Vacation rentals in Siesta Key, FL with a pool

Explore 650 vacation rentals, homes, and villas with pools in Siesta Key, FL for your next getaway or business trip. Step outside to your own private or shared pool and into a home filled with premium amenities such as Air Condition Homes, Homes with Free Parking and Best Affordable Homes. Throughout your stay, unwind poolside, soak up the sun, and enjoy an outdoor space designed for relaxation. With options starting as low as $48 per night and homes offering up to 15 bedrooms and 17 bathrooms, it's easy to book a comfortable, personalized stay. You'll also have access to high-speed Wi-Fi and 24/7 local support, creating a more secure, connected atmosphere for your trip. Marriott Bonvoy members enjoy the added benefit of earning points on every stay, so each trip's more rewarding than the last. Book your next poolside escape with Homes & Villas by Marriott.

650 Homes with Pools in Siesta Key

Siesta Sun Oasis - 5545

Sarasota, FL, US
5 Bedrooms 10 Guests
Aug 28 - Sep 4
$844 night

☀️ Siesta Sun Oasis | Private Pool, Walk to Siesta Key Beach, Game Room & Large Backyard Court 💖 Why You’ll Love This Home Siesta Sun Oasis offers a spacious island retreat designed for gathering, relaxing, and enjoying time outdoors. With five bedrooms and a large backyard built for recreation, this home makes it easy to balance beach days with time spent at home. A complimentary 6-passenger golf cart is included with bookings through November 1st and ready upon arrival, courtesy of Robin Hood Rentals, making it easy to explore Siesta Key’s beaches, shops, and restaurants. The private pool and oversized concrete court create a setting where everyone can find their favorite way to unwind, from poolside lounging to friendly games of pickleball or soccer. Inside, the home blends comfort and functionality with generous living spaces and a well-equipped kitchen featuring LG appliances, a wine cooler, and a combination microwave, air fryer, and oven for easy meals and entertaining. Siesta Sun Oasis provides the space to enjoy every part of your stay. 👨‍👩‍👧 Perfect For Families, multi-generational groups, or friends looking for a spacious Siesta Key stay with outdoor activities, poolside relaxation, and room for everyone to spread out. 🎞️ Imagine This Start the day outside as the morning sun fills the backyard. Plan the day around a quick trip to Siesta Key Beach before returning home to cool off in the private pool. In the afternoon, challenge friends to a game on the backyard court, perfect for pickleball, soccer, or casual outdoor play while others relax by the pool or gather inside around the pool table. As evening settles in, the backyard becomes the heart of the home. Start up the grill, share stories from the day, and enjoy the warm island air before retreating indoors to comfortable bedrooms across the home. 🛌 Where You’ll Sleep • Bedroom 1: King Bed, Ensuite Bath, TV • Bedroom 2: King Bed, TV • Bedroom 3: Queen Bed, TV • Bedroom 4: Queen Bed, Ensuite Jack and Jill Bath, TV • Bedroom 5: Queen Bed, Ensuite Jack and Jill Bath, TV • Office: Sleeper Sofa (Connected to the Primary Suite) 📍 Explore the Area • 0.5 Miles to Siesta Key Beach – Powdery White Sand and Gulf Swimming • 1.5 Miles to Siesta Key Village – Restaurants, Coffee Shops, and Island Boutiques • 1.6 Miles to Crescent Beach – A Scenic Stretch of Shoreline with Calm Waters • 6.0 Miles to Downtown Sarasota – Bayfront Parks, Arts, and Dining • 9.2 Miles to St. Armands Circle – Upscale Shopping and Restaurants ⌛ Book Today: Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection. 🔎 Need to Know: Starter packs of kitchen and toiletry essentials are provided for your first couple of nights. Free high-speed WiFi is included. We happily welcome one small dog (up to 25 lbs) with a $250 pet fee—breed guidelines apply to ensure a safe and comfortable stay for everyone. Please reach out prior to booking so we can help make your pup’s stay just as wonderful as yours.

Gulf Birdie - 5551

Siesta Key, FL, US
3 Bedrooms 9 Guests
Aug 18 - 25
$767 night

🌴 Gulf Birdie | Waterfront Pool, Hot Tub & Putting Green, 0.5 Miles to Siesta Beach 💖 Why You’ll Love This Home Canal waters shimmer in the backyard as palm fronds sway overhead. A breeze flows while you grill in the gourmet outdoor kitchen. Lounge in the private heated pool or spa, challenge friends on the putting green, and enjoy a fire pit under a starry Florida sky - all just 0.5 miles from Siesta Key’s white sand beach. Inside, soft coastal tones and textures create a serene space to unwind in style. 👨‍👩‍👧 Perfect For Families, couples, or multi-generational groups seeking a luxurious, beachy escape with walkable Gulf access. 🎞️ Imagine This Start your morning with coffee on the screened lanai as the canal glistens in the sun. Slip into the pool for a refreshing swim, then stroll 0.5 miles to Siesta Beach for soft white sands and turquoise waters. Back home, grill lunch in your private outdoor kitchen while the kids practice putts on the green or paddle along the canal. As the sun sets, soak in the spa and gather around the fire pit with cocktails. Inside, comfortable coastal décor and thoughtful touches invite you to relax after a day of fun and sun. 🛌 Where You’ll Sleep • Bedroom 1: King Bed, Ensuite Bath, TV, Private Balcony • Bedroom 2: Queen Bed + Twin Bed, Shared Hallway Bath, TV • Bedroom 3: Two Twin Beds, Shared Hallway Bath, TV • Bonus Room: Queen Sleeper Sofa, Main Living Area 📍 Explore the Area • Waterfront Setting – Paddle the Canal or Soak in the Views from Your Own Backyard • 0.5 Miles to Siesta Key Beach – Walk or Bike to One of the Country’s Top-Rated Beaches • 1.5 Miles to Siesta Key Village – Island Dining, Boutiques, Ice Cream Shops, and Coastal Nightlife ⌛ Don’t Wait - This waterfront gem books quickly. Your reservation includes peace of mind with our CottageClean program, featuring a 6-hour deep clean and 35-point inspection. 🔎 Need to Know: This pool is heated from November 15th to April 15th. There is a 1 rental per 30 day period, per Sarasota, FL ordinance, contact us for more information. The primary guest making the reservation must be at least 26 years of age.

Siesta Springs

Sarasota, FL, US
5 Bedrooms 14 Guests
Aug 22 - 25
$1,099 night

Vunique Vacations was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. This home was built for vacation! With balconies on all levels and a roof top deck that is 50 feet above the ground, there are views everywhere! The heated saltwater pool and spa area are an homage to Florida’s famous natural springs (without the alligators of course). The pool area has crystal clear water and has a rock waterfall with integrated water slide and a rock jumping platform and rope swing for those brave enough to literally slide, swing, or jump in! There is also a large sun shelf with bubblers, and lights. At the backside of the pool, you’ll find a turf area that extends the playing and lounging areas and includes putt-putt golf. Adjacent to the pool is the covered patio area that features 2 smart TVs, outdoor grill (natural gas), and plenty of covered seating and dining options. These spaces are all within the fenced backyard for privacy and security making it family friendly and perfect for the home’s pet friendly policy (fees and restrictions apply). This nearly 3,600 square foot home provides views and balconies on all levels. This home has an elevator with service to all floors (except the rooftop). This home provides 5 bedrooms (all with en suite baths and balcony access), with 2 master bedrooms, and a bunk room that was outfitted to be a kids dream with a rock-climbing wall, smart TV and seating, and arcade and gaming consoles! There are 4 king beds and 2 custom full over full bunk beds in this home; and 5 full baths and 2 half baths. The home comfortably sleeps 14 people in beds. The great room is set up as a family friendly gathering space that includes the kitchen, living, dining areas, and a balcony with additional seating. The kitchen is fully stocked, and we mean that because we know how important it is to you, our valued guests! Not only is it stocked, but it’s also stocked with the products and manufacturers you trust. This home also offers a club room or secondary living space with multiple games, wet bar that supports this space, and a balcony with seating that provides access to the home’s 50-foot-high rooftop deck! Floor Plan Description (by level): Ground Level: Free parking for up to 4 vehicles (2 in garage, 2 in driveway). The fenced pool and backyard area (pet friendly - fees and restrictions apply), including the covered patio space and pool that was previously described, and there are ceiling fans throughout the space. The home’s ping pong table, corn hole boards, poolside basketball hoop, outdoor connect 4, bocce ball and beach equipment can be found here that includes 2 beach wagons, 2 coolers, 10 beach chairs, and 4 bikes. We include a full refrigerator and freezer (with ice maker) here as well so your beach prep and breakdown, and your use of the home and pool is that much easier. These appliances can also be used to support your pool days and time at home as well. You’ll also access the home’s main entrance foyer with elevator and stair access to the home’s three (3) living levels and rooftop deck above. The First Level of Living (2nd Floor): The great room has a fully stocked kitchen that includes a large pantry, cooktop with hood vent, double ovens (2), full sized refrigerator (with ice maker) and freezer, 2 trash and recycling pull-outs, 2 dishwashers, microwave, toaster, coffee maker, and is very well appointed with cookware, bakeware, dishware, cutlery, and specialty items like crockpots, blenders, and more. If you have any questions on kitchen supplies, our reservationists would be happy to provide more details. The living area is very comfortably set up with smart TV and seating, with access to a balcony with additional dining seating. The dining area here seats 14 people comfortably via a 8-person custom dining table, 6-person kitchen island bar top. Master bedroom 2 has double -Juliet balconies’ accessed from the bedroom and bath, a king bed, and an en suite bathroom with double faucet vanity and walk-in shower. There is a half bath on this floor. The Second Level of Living (3rd Floor): You’ll find 3 bedrooms on this level. Bedrooms 3 and 4 both have balcony access, a king bed, and an en suite bath with double faucet vanity and walk-in shower. Bedroom 5 has a rock-climbing wall built into the room that every child is going to love, a seating area with smart TV, arcade game table, and balcony access (with parental safety features), 2 full over full bunk beds, and an en suite bathroom with vanity and shower/bathtub combination. There is also an oversized laundry room on this level with utility sink and 2 stackable washer/dryer units. The Third Level of Living & Rooftop Deck (4th Floor): Master bedroom 1 has Gulf views, balcony access, window nook, walk in closet, and a large en suite bathroom with 2 vanities, walk-in double shower, freestanding bathtub, and private water closet. The club room has Gulf views, dry bar, seating, workspace, 2 smart TVs, dining/card table, Wall Scrabble, and Nintendo Switch gaming console in this room. The dry bar has a beverage refrigerator with ice maker and trash pull-out. It also has a half bath, and a balcony with stair access to the roof top deck (both with Gulf views). The rooftop deck is perfect for enjoying sunrise over Siesta and greater Sarasota, or sunset over the Gulf of Mexico. So, be sure to grab a book, a coffee or cocktail, and enjoy the sea breeze and Florida sun from this amazing elevated outdoor living space that overlooks all of Siesta Key. These are great indoor and outdoor entertainment spaces! https://www.youtube.com/watch?v=WNPfYYiwzlM The North and South village entertainment districts can be accessed easiest by bike, golf cart, car, or free trolley. If you want to explore further, without the hassle of driving, you’ll find multiple stops nearby for the free trolley that provides transportation service to the entirety of Siesta Key. You’re also just a quick drive or Uber/Lyft (10-15 minutes) to downtown Sarasota for access to the amazing Sarasota Performing Arts scene, and numerous fantastic restaurants, shops, marinas, bars and entertainment, and more. And, day trips to Lido Key and Anna Maria Island are just 30 minutes away, as well as the amazing theme parks of Tampa and Orlando that are all just 1-2 hours away! Please note that this home is in close proximity to an ongoing construction project. Please inquire with the host for more information. This home provides private beach access. Access to the private beach is controlled. Please accurately list the number of travelers associated with your reservation, and our team will contact you and walk you through the easy to follow private beach rules. This Siesta Key luxury vacation rental features Smart TVs with cable and streaming services, as well as Free Wi-Fi throughout the property - including the outside areas for complete coverage for all your work or personal needs. TVs in all bedrooms. Accessibility - in addition to the home’s elevator access to all levels (except rooftop), most doorways and walkways are 30 inches or larger and walk-in showers featured in most bathrooms. Please see the Photos, 3D Tour, & Video for this home for exact information. *Don’t forget to check out our Matterport 3D Tour for this home* And, if you still have any questions concerning our homes, rates, availability calendar, amenities, policies, or otherwise, please contact our team of professional reservationists and we will be happy to assist you. We want you to fully understand what you are booking, and yes, an actual human team member is available to help! You are just a couple of clicks away from paradise!

Serving Sunset

Siesta Key, FL, US
5 Bedrooms 14 Guests
Aug 27 - 30
$1,153 night

Vunique Vacations was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. People love beach volleyball here, so we designed a heated saltwater pool and spa with a volleyball theme! The pool volleyball area is nearly 20 feet by 30 feet, and it’s separated by a wall and landscaping from the remainder of the pool area and covered patio, so the effects of the volleyball game don’t extend beyond the court! The pool also has a waterslide, and a large sun shelf with seating, bubblers, lights, and staircase that leads to the pool. At the backside of the pool, you’ll find a turfed area with putt-putt golf. Adjacent to the pool is the covered patio area that features 3 smart TVs, outdoor grill (natural gas), and plenty of covered seating and dining. These spaces are all within the fenced backyard for privacy and security making it family friendly and perfect for the home’s pet friendly policy (fees and restrictions apply). This nearly 3,600 square foot home provides views and balconies on all levels, including the rooftop deck that is over 50 feet above the ground. This home has an elevator with service to all floors (except the rooftop). This home provides 5 bedrooms (all with en suite baths and balcony access) and there is a rock-climbing wall in the bunk room! There are 4 king beds and 2 custom full over full bunk beds; and 5 full baths and 2 half baths. The home comfortably sleeps 14 people in beds. The great room is family friendly and includes the kitchen, living, dining areas, and balcony. The kitchen is fully stocked, and we mean that because we know how important it is to you, our valued guests! Not only is it stocked, but it’s also stocked with the products and manufacturers you trust. This home also has a club room or secondary living space with multiple games, wet bar that supports this space, and the balcony that provides access to the home’s 50-foot-high rooftop deck! Floor Plan Description (by level): Ground Level: Free parking for up to 4 vehicles. The fully fenced pool and backyard area (pet friendly – fees and restrictions apply), includes the covered patio space and pool that was previously described and there are ceiling fans throughout. The home’s ping pong table, corn hole boards, poolside basketball hoop, outdoor connect 4, bocce ball and beach equipment can be found here that includes 2 beach wagons, 2 coolers, 10 beach chairs, and 4 bikes. We include a full refrigerator and deep freezer nearby for easy storage of food, drinks, and ice, so your beach prep and breakdown are that much easier.? These appliances can also be used to support your pool days and time at home. You’ll also access the home’s main entrance foyer with elevator and stair access to the home’s three (3) living levels and rooftop deck above. The First Level of Living (2nd Floor): The great room has a fully stocked kitchen with a large pantry, cooktop with hood vent, double ovens (2), full sized refrigerator (with ice maker) and freezer, 2 trash/recycling pull-outs, 2 dishwashers, microwave, toaster, coffee maker, and is very well appointed with cookware, bakeware, dishware, cutlery, and specialty items like crockpots, blenders, and more. If you have any questions on kitchen supplies, our reservationists would be happy to provide more details. The living area is very comfortable with balcony access and the dining area seats 13 people comfortably via an 8-person dining table, 5-person kitchen island bar top. Master bedroom 2 has double ‘Juliet balconies’ accessed from the bedroom and bath, a king bed, and an en suite bathroom with double faucet vanity and walk-in shower. There is a half bath on this floor. The Second Level of Living (3rd Floor): Bedrooms 3 and 4 both have balcony access, a king bed, and an en suite bath with double faucet vanity and walk-in shower. Bedroom 5 has a rock-climbing wall built into the room that every child is going to love, a seating area with smart TV, balcony access (with parental safety features) and, 2 full over full bunk beds, and an en suite bathroom with vanity and shower/bathtub combination. There is also an oversized laundry room on this level with utility sink and 2 stackable washer/dryer units. The Third Level of Living & Rooftop Deck (4th Floor): Master bedroom 1 has Gulf views, balcony access, walk in closet, and a large en suite bathroom with 2 vanities, walk-in double shower, freestanding bathtub, and private water closet. The club room has a wet bar, seating, workspace area, and games including Nintendo Switch gaming console and shuffleboard in this room. The wet bar has a sink, beverage and wine refrigerators, ice maker, and trash pull-out. It also has a half bath, and a balcony and stair access to the roof top deck (both with Gulf views). The rooftop deck is perfect for enjoying sunrise over Siesta and greater Sarasota, or sunset over the Gulf of Mexico. So, be sure to grab a book, a coffee or cocktail, and enjoy the sea breeze and Florida sun from this amazing elevated outdoor living space that overlooks all of Siesta Key. These are great indoor and outdoor entertainment spaces!? https://www.youtube.com/watch?v=eHzunY8jO74 Private beach! This amazing home is a few steps from the sands of the world-famous Siesta Key Beach and the private section of it that is just for those on this private street! It’s centrally located to the North and South Siesta village entertainment districts and all the restaurants, entertainment, shopping, grocers, and more on the Key. Everything can be accessed by bike, golf cart, car, or free trolley. If you want to explore further, without the hassle of driving, you’ll find multiple stops nearby for the free trolley that provides transportation service to the entirety of Siesta Key. You’re also just a quick drive or Uber/Lyft (10-15 minutes) to downtown Sarasota for access to the amazing Sarasota Performing Arts scene, and numerous fantastic restaurants, shops, marinas, bars and entertainment, and more. And, day trips to Lido Key and Anna Maria Island are just 30 minutes away, as well as the amazing theme parks of Tampa and Orlando that are all just 1-2 hours away! This home provides private beach access. Access to the private beach is controlled. Please accurately list the number of travelers associated with your reservation, and our team will contact you and walk you through the easy to follow private beach rules. This Siesta Key luxury vacation rental features Smart TVs with cable and streaming services, as well as Free Wi-Fi throughout the property - including the outside areas for complete coverage for all your work or personal needs. TVs in all bedrooms. Accessibility - in addition to the home’s elevator access to all levels, most doorways and walkways are 30 inches or larger and walk-in showers featured in most bathrooms. Please see the Photos, 3D Tour, & Video for this home for exact information. *Don’t forget to check out our Matterport 3D Tour for this home* And, if you still have any questions concerning our homes, rates, availability calendar, amenities, policies, or otherwise, please contact our team of professional reservationists and we will be happy to assist you. We want you to fully understand what you are booking, and yes, an actual human team member is available to help! You are just a couple of clicks away from paradise!

Blue Lagoon

Sarasota, FL, US
5 Bedrooms 14 Guests
Aug 24 - 27
$920 night

Vunique Vacations was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. Private Beach! This amazing home is just steps from the sands of the world-famous Siesta Key Beach and the private section of it that is just for those on this private street! The heated saltwater pool and spa has a rock waterfall with integrated water slide, rock jumping platform, poolside basketball hoop, bocce ball and rope swing for those brave enough to literally slide, swing, or jump in! There is also a large sun shelf with loungers, bubblers, and lights. At the backside of the pool, there is a turf area that includes putt-putt golf. Adjacent to the pool is the covered patio area that has 3 smart TVs, outdoor grill (natural gas), and plenty of covered seating and dining. These spaces are all within the fenced backyard for privacy and security making it family friendly and perfect for the home’s pet friendly policy (fees and restrictions apply). This nearly 3,600 square foot home provides views and balconies on all levels, including the rooftop deck that is over 50 feet above the ground. This home has an elevator with service to all floors (except the rooftop). This home has 5 bedrooms (all with en suite baths and balcony access); and 5 full baths and 2 half baths. There are 4 king beds and 2 custom Queen over Queen bunk beds. The home comfortably sleeps 14 people in beds. The great room is family friendly and includes the kitchen, living, dining areas, and balcony. The kitchen is fully stocked, and we mean that because we know how important it is to you, our valued guests! Not only is it stocked, but it’s also stocked with the products and manufacturers you trust. This home also has a club room with multiple games, bar area, and a balcony with seating that provides access to the home’s 50-foot-high rooftop deck! Floor Plan Description (by level): Ground Level: Free parking for up to 4 vehicles. The fully fenced pool and backyard area (pet friendly – fees and restrictions apply) includes the covered patio space and pool that was previously described with ceiling fans throughout. The home’s ping pong table, corn hole boards, outdoor connect 4, and beach equipment can be found here that includes 2 beach wagons, 2 coolers, 10 beach chairs, and 4 bikes. We include a full refrigerator and deep freezer nearby for easy storage of food, drinks, and ice, so your beach prep and breakdown are that much easier.? These appliances can also be used to support your pool days and time at home. You’ll also access the home’s main entrance foyer with elevator and stair access to the home’s three (3) living levels and rooftop deck above. The First Level of Living (2nd Floor): The great room has a fully stocked kitchen with a large pantry, cooktop with hood vent, double ovens (2), full sized refrigerator (w/ ice maker) and freezer, trash/recycling pull-outs, 2 dishwashers, microwave, toaster, coffee maker, and is very well appointed with cookware, bakeware, dish-ware, cutlery, and specialty items like crockpots, blenders, and more. If you have any questions on kitchen supplies, our team would be happy to provide more details. The living area is very comfortable and the dining area here seats 14 people comfortably via a 8-person dining table, 6-person kitchen bar top. Master bedroom 2 has double ‘Juliet balconies’, a king bed, and an en suite bathroom with double faucet vanity and walk-in shower. There is a half bath on this floor. The Second Level of Living (3rd Floor): Bedrooms 3 and 4 both have balcony access, a king bed, and an en suite bath with double faucet vanity and walk-in shower. Bedroom 5 has balcony access (with parental safety features), 2 smart TVs, seating, workspace with TVs to connect your computer for dual screens for work or computer gaming, 2 queen over queen bunk beds, city closets, and an en suite bathroom with vanity and shower/bathtub combination. There is also an oversized laundry room on this level with utility sink and 2 stackable washer/dryer units. The Third Level of Living & Rooftop Deck (4th Floor): Master bedroom 1 has Gulf views, balcony access, walk in closet, and a large en suite bathroom with 2 vanities, walk-in double shower, freestanding bathtub, and private water closet. The club room has a wet bar, seating, and games (Nintendo Switch 2, air hockey and wall Scrabble). The bar has a sink, beverage and wine refrigerators, ice maker, and trash pull-out. It also has a half bath, and a balcony with stair access to the roof top deck (both with Gulf views). The rooftop deck is perfect for enjoying sunrise or sunset. So, be sure to grab a book, a coffee or cocktail, and enjoy the sea breeze and Florida sun from this amazing elevated outdoor living space that overlooks all of Siesta Key. These are great indoor and outdoor entertainment spaces! https://www.youtube.com/watch?v=VrmBWqJtdvo North and South Siesta village entertainment districts and all the restaurants, entertainment, shopping, grocers, and more on the Key can be accessed by bike, golf cart, car, or free trolley. If you want to explore further, without the hassle of driving, you’ll find multiple stops nearby for the free trolley that provides transportation service to the entirety of Siesta Key. You’re also just a quick drive or Uber/Lyft (10-15 minutes) to downtown Sarasota for access to the amazing Sarasota Performing Arts scene, and numerous fantastic restaurants, shops, marinas, bars and entertainment, and more. And, day trips to Lido Key and Anna Maria Island are just 30 minutes away, as well as the amazing theme parks of Tampa and Orlando that are all just 1-2 hours away! This home provides private beach access. Access to the private beach is controlled. Please accurately list the number of travelers associated with your reservation, and our team will contact you and walk you through the easy to follow private beach rules. This Siesta Key luxury vacation rental features Smart TVs with cable and streaming services, as well as Free Wi-Fi throughout the property - including the outside areas for complete coverage for all your work or personal needs. TVs in all bedrooms. Accessibility - in addition to the home’s elevator access to all levels, most doorways and walkways are 30 inches or larger and walk-in showers featured in most bathrooms. Please see the Photos, 3D Tour, & Video for this home for exact information. *Don’t forget to check out our Matterport 3D Tour for this home* And, if you still have any questions concerning our homes, rates, availability calendar, amenities, policies, or otherwise, please contact our team of professional reservationists and we will be happy to assist you. We want you to fully understand what you are booking, and yes, an actual human team member is available to help! You are just a couple of clicks away from paradise!

Sand Dollar Cottage - 910

Siesta Key, FL, US
3 Bedrooms 8 Guests
Aug 18 - 25
$632 night

🌴 Sand Dollar Cottage | Canal-Front Oasis + Private Heated Pool 💖 Why You’ll Love This Home Float into coastal serenity at this canal-front escape on Siesta Key. Paddle from your private dock, dine in the screened lanai, or cool off in the private heated pool—all just a 15-minute walk to Siesta Key Beach. This home blends laid-back luxury with island charm. 👨‍👩‍👧 Perfect For Ideal for families, couples, or groups looking for a peaceful waterfront retreat near the beach and vibrant Siesta Key Village 🎞️ Imagine This You wake to the gentle shimmer of water just outside your window. Brew a cup from the Keurig, then sip it poolside as the sun rises over the canal. After breakfast in the screened lanai, grab a kayak and explore quiet mangrove-lined waterways. Back at home, rinse off in the outdoor shower, then stroll 0.7 miles to Siesta Key Beach for a sunny afternoon on the powdery sands. Return in time for sunset cocktails by the pool or grill up a fresh catch and gather around the dining table to recap the day’s adventures. When night falls, settle into plush beds or stream a movie on one of four HDTVs—ready to do it all again tomorrow. 🛌 Where You’ll Sleep Bedroom 1: King Bed, ensuite bath, ground floor, canal views, TV Bedroom 2: Queen Bed, shared bath, ground floor, TV Bedroom 3: Two Twin Beds, shared bath, ground floor, TV Additional: Two portable cots in bedroom closets (linens provided) 📍 Explore the Area • 0.7 miles to Siesta Key Beach • 1.4 miles to Siesta Key Village – restaurants, boutiques, live music • Easy walk or bike to shops, cafes, and island market • Nearby kayak routes, fishing spots, and island shuttle pick-up • Peaceful residential street with relaxed, coastal energy 📝 Don’t wait—this home books fast. Your reservation includes peace of mind with our CottageClean™ program - a 6-hour deep clean and 35-point inspection. ✨ Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. Free high-speed WiFi included. This pool is heated between November 15 - April 15. If any guest has difficulty with stairs, please contact us for alternative accommodations. Sarasota ordinance allows one rental per 30-day period—contact us with questions before booking.

The Sun Dial - 827

Siesta Key, FL, US
4 Bedrooms 12 Guests
Aug 26 - Sep 2
$913 night

🌴 The Sun Dial | Waterfront Pool Home + Walk to Beach 💖 Why You’ll Love This Home Nestled on the peaceful canals of Siesta Key, The Sun Dial offers the perfect fusion of luxury, privacy, and adventure. From sunrise coffee on your private balcony to kayaking the calm waterways at sunset, this home was made for unforgettable moments. With a private heated pool, spacious layout, and just 1 mile from world-famous Siesta Key Beach, every detail is designed for comfort, style, and coastal charm. 👨‍👩‍👧 Perfect For Ideal for multi-generational families, couples traveling together, or groups seeking high-end comfort with waterfront access. 🎞️ Imagine This... You wake to the glow of the morning sun reflecting off the water, brewing coffee in your private master suite kitchenette before stepping onto the balcony to watch kayakers drift by. The breeze is warm, the canal still. Later, everyone gathers in the open-concept kitchen and living area—kids splash in the large private pool while adults sip mimosas under swaying palms. Maybe someone spots the custom sun dial in the garden and snaps a photo—it’s little touches like that which make this place feel different. In the afternoon, you launch a kayak and explore the serene backwater channels, or take the short stroll to Siesta Key Beach (1 mile) for an ocean swim. As the day winds down, the group heads to Siesta Key Village (1.8 miles) for fresh seafood and live music. Back home, the laughter continues under starlit skies on your private lanai. The Sun Dial isn’t just a place to stay—it’s part of the story you’ll tell. 🛌 Where You’ll Sleep • Bedroom 1: King Bed, Ensuite Bath, Top Floor, TV, Private Balcony, Kitchenette • Bedroom 2: King Bed + Twin Bunk Bed, Shared Bath, Main Floor, TV • Bedroom 3: King Bed, Ensuite Bath, Main Floor, TV • Bedroom 4: King Bed, Shared Bath, Main Floor, TV • Bonus Space: Queen Sleeper Sofa – Living Room 📍 Explore the Area • 1.0 mile to Siesta Key Beach (walkable via shaded neighborhood roads) • 1.8 miles to Siesta Key Village – shops, restaurants, nightlife • Canal access on-site – 2 kayaks provided • Watch sunsets, explore barrier island nature, or walk to dinner by the sea ⌛ Don’t Miss Out This luxury home books quickly, especially in high season. Your stay includes peace of mind with our CottageClean™ program: a six-hour deep clean and a 35-point inspection before every guest arrival—so you can vacation worry-free from the moment you arrive. 📝 Need to Know - There is a 1 rental per 30 day period, per Sarasota, FL ordinance, contact us for more information. Reservation must follow under the accordance of the Sarasota County code regulations. This pool is heated from November 15th to April 15th. Exterior security cameras are installed at the front door for security purposes only. No cameras are located inside the home or in private guest areas.

Vantage Point

Siesta Key, FL, US
6 Bedrooms 18 Guests
Aug 25 - 28
$2,013 night

Vunique Vacations was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. Welcome to Vantage Point, a standout Siesta Key retreat designed for elevated group getaways just moments from the beach. With 6 bedrooms, 6 full bathrooms, and 2 half baths, the home comfortably sleeps up to 18 guests and is thoughtfully designed so everyone can gather without feeling crowded. From a resort-style pool with a sun shelf, waterslide, and heated spa to ping pong, poolside basketball hoop, putt putt, corn hole, rooftop fire pit, and multiple outdoor gathering spaces, the home is built around fun, connection, and easy downtime. Inside and out, every level offers something memorable—from relaxed mornings by the pool to evenings spent together under the open sky. Come experience Vantage Point, where the house itself becomes part of the vacation! Floor Plan Description (by level): Ground Level: This level includes a 2-car garage with an EV charger, along with driveway parking for 4 additional vehicles, plus elevator and stair access to all levels of the home, including the rooftop. Through the foyer you’ll make your way into a covered pool area with a resort-style pool featuring a sun shelf, waterslide, and heated spa, and a putt putt course located directly next to the waterslide. The covered pool area offers generous space to gather, with plenty of seating for your whole group, additional bar-height dining, 3 HD TV’s and soft seating arranged throughout the space. A natural gas grill is set up nearby for easy poolside cooking. There is also a pink pong table and a corn hole set up so nobody in your group will be bored. First Level of Living (Main Living Level): This level brings everyone together indoors with an open, inviting layout centered around a chef’s kitchen designed for group stays. The kitchen features double ovens, a large island with seating for 5, and a butler’s pantry equipped with a beverage fridge with ice maker and a microwave drawer. The main dining table seats 12, and the living room opens to a spacious balcony with dining for 10, with stairs leading directly down to the pool area for easy indoor-outdoor flow. This floor also includes a half bath and 2 bedrooms. Master Bedroom 1 features a king bed, an en suite bathroom with a freestanding tub, walk-in shower, and single vanity with 2 faucets, along with balcony access with seating for 2 overlooking the pool area. Bedroom 4 offers a king bed and an en suite bathroom with a single-sink vanity and walk-in shower. A dedicated laundry room on this level includes a utility sink, 2 stackable washer and dryer units, and a clothes hanging rod with shelving. Second Level of Living: The second living level is designed for entertainment and private retreats. A dedicated club room features an media centre with 85-inch TV w/surround sound, two theater-style sofas with seating for 7, Nintendo Switch gaming console, a built-in media wall with 2 workstations, and a beverage refrigerator with ice maker. Sliding doors open to a balcony with soft seating for 8, which is also accessible from Master Bedroom 3 and Bedroom 5. This level includes 4 bedrooms. Both Master Bedroom 3 has a king size bed, built in work station, walk-in closet, balcony access with Gulf Views and a en suite bath with both shower and soaking tub. Master Bedroom 2 also includes balcony access with soft seating for 2 overlooking the pool area. Bedroom 5 has a king size bed, en suite bathroom with shower and access to the balcony shared with the Club Room and Master Bedroom 3. Bedroom 6 serves as the bunk room and includes 2 full-over-full bunk beds, a bathroom with a walk-in shower, one sink with 2 faucets, and an additional sink located just outside the bathroom for added convenience. Rooftop Deck: The rooftop at Vantage Point offers a relaxed escape above it all, with elevator access, a half bath, and sweeping Gulf views. A covered rooftop lounge features 2 HDTVs, soft seating, bar height dining and a bar area with a beverage fridge with ice maker, creating a comfortable spot to gather and unwind. There is also an outdoor fire put with seating and multiple chaise lounges provided for you to enjoy the sunshine, coastal breeze, and Gulf views stretching out toward the water. Whether you’re spending time together during the day or enjoying a quiet moment at sunset, the rooftop offers a memorable setting that feels elevated without being overdone. https://www.youtube.com/watch?v=ObHNK8bU7bw This home is located just across the street from the north entrance to the public Siesta Key Beach. Siesta Key Village and all the restaurants, entertainment, shopping, grocers, and more on the Key can be accessed by bike, golf cart, car, or free trolley. If you want to explore further, without the hassle of driving, you’ll find multiple stops nearby for the free trolley that provides transportation service to the entirety of Siesta Key. You’re also just a quick drive or Uber/Lyft (10-15 minutes) to downtown Sarasota for access to the amazing Sarasota Performing Arts scene, and numerous fantastic restaurants, shops, marinas, bars and entertainment, and more. And, day trips to Lido Key and Anna Maria Island are just 30 minutes away, as well as the amazing theme parks of Tampa and Orlando that are all just 1-2 hours away! This Siesta Key luxury vacation rental features Smart TVs with cable and streaming services, as well as Free Wi-Fi throughout the property - including the outside areas for complete coverage for all your work or personal needs. TVs in all bedrooms. Accessibility - in addition to the home’s elevator access to all levels, most doorways and walkways are 30 inches or larger and walk-in showers featured in most bathrooms. Please see the Photos, 3D Tour, & Video for this home for exact information. *Don’t forget to check out our Matterport 3D Tour for this home* And, if you still have any questions concerning our homes, rates, availability calendar, amenities, policies, or otherwise, please contact our team of professional reservationists and we will be happy to assist you. We want you to fully understand what you are booking, and yes, an actual human team member is available to help! You are just a couple of clicks away from paradise!

Beach Palm Villa - 5533

Siesta Key, FL, US
4 Bedrooms 12 Guests
Aug 18 - 25
$767 night

🌴 Beach Palm Villa | Heated Pool + Walk to Siesta Key Beach 💖 Why You’ll Love This Home Immerse yourself in coastal luxury at Beach Palm Villa, a private Siesta Key retreat just a short stroll from world-famous Siesta Key Beach. Designed for effortless comfort and style, this 4-bedroom oasis combines resort-level amenities with the relaxed rhythm of island living. From poolside lounging to family dinners under the stars, every moment here feels like a treasured memory in the making. 👨‍👩‍👧 Perfect For Multi-generational families, friend groups, or couples seeking a luxurious island escape within walking distance to the beach. 🎞️ Imagine This You wake to the sound of rustling palms and the promise of another sun-filled day. Brew a cup of coffee in the gourmet kitchen and step outside to your private heated pool, where the morning light dances across the water. Spend your day soaking in the sun, strolling to Siesta Key Beach just 10 minutes away, or perfecting your short game on the outdoor putting green. As evening falls, laughter fills the air around the fire pit while the sky glows in shades of coral and gold. Here, every detail invites you to relax, reconnect, and make lifelong memories. The heart of Beach Palm Villa is its modern, fully equipped kitchen, perfect for culinary creativity and casual gatherings alike. Enjoy regular and Keurig coffee makers, a dishwasher, stainless-steel appliances, and a water purification system that ensures every sip and ingredient is as refreshing as the Gulf breeze. With plenty of prep space and elegant design, cooking here feels effortless and inspiring. 🛌 Where You’ll Sleep • Bedroom 1: King Bed, Ensuite Bath, TV • Bedroom 2: King Bed, Shared Bath, TV • Bedroom 3: Queen Bed, Shared Bath, TV • Bedroom 4: Two Twin Bunk Beds with Trundles, Shared Bath, TV 📍 Explore the Area • 0.5 Miles (10-Minute Walk) to Siesta Key Beach • 0.7 Miles to Siesta Key Village – Dining, Shopping, and Nightlife • 7.0 Miles to Downtown Sarasota – Arts, Culture, and Entertainment • 9.6 Miles to St. Armands Circle – Upscale Boutiques and Restaurants • 11.5 Miles to Sarasota-Bradenton International Airport (SRQ) ⌛ Don’t wait—this home books fast. Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection. 🔎 Need to Know: There is a 1 rental per 30 day period, per Sarasota, FL ordinance, contact us for more information. Reservation must follow under the accordance of the Sarasota County code regulations. The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather.

Isla Amor - 86

Siesta Key, FL, US
5 Bedrooms 11 Guests
Aug 23 - 30
$1,073 night

🌴 Isla Amor | Escape to a Luxury Waterfront Home with Heated Pool & Stunning Views in Siesta Key 💖 Why You’ll Love This Home Imagine waking up to serene canal views, stepping out onto your private balcony, and spending your day basking in the sun by a resort-style heated pool. Isla Amor delivers an unforgettable escape—romantic, family-ready, and infused with island charm. With five thoughtfully appointed bedrooms, stylish open-concept interiors, and outdoor living spaces made for memory-making, this Siesta Key gem is a tranquil paradise tucked in the sought-after Palm Island enclave. 👨‍👩‍👧 Perfect For Families, couples, and adult groups looking for a peaceful waterfront home near Siesta Key Beach—ideal for extended stays, celebrations, or a quiet, luxurious reset. 🎞️ Imagine This Begin your day with coffee on the main floor balcony, the canal glistening below and palms swaying in the breeze. Head inside to the gourmet kitchen to whip up breakfast, or grab your beach gear—just a 7-minute stroll (0.3 miles) and you’re on Siesta Key Beach’s iconic powder-white sand. Spend the afternoon lounging by the heated pool or enjoying drinks at the outdoor wet bar with a mini fridge. As the sun sets, gather around the table-top fire pit or dine al fresco in the screened-in porch. Whether you’re sharing laughs at the indoor bar or winding down in your plush king suite, Isla Amor wraps every moment in warmth and comfort. 🛌 Where You’ll Sleep • Bedroom 1: King Bed, Ensuite, Main Floor, TV • Bedroom 2: King Bed, Shared Bath, Upper Floor, TV • Bedroom 3: King Bed, Shared Bath, Upper Floor, TV • Bedroom 4: 2 Twin Beds, Shared Bath, Upper Floor, TV • Bedroom 5: 3 Twin Modular Beds, Shared Bath, Upper Floor, TV 📍 Explore the Area • 0.3 Miles to Siesta Key Beach – A 7-Minute Walk to the Soft Quartz Sand and Turquoise Water • 1.2 Miles to South Siesta Key Village – Boutique Shopping, Dining, and Live Music • Canal-Front Living with Peaceful Coastal Ambiance • Quick Access to Kayaking, Paddle Boarding, and Local Excursions • Quiet Palm Island Neighborhood with Minimal Through-Traffic ⌛ Don’t wait—this home books fast. Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection. 📝 Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. Free high-speed WiFi throughout. The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. If any guest has difficulty with stairs, please contact us for alternative accommodations. Please note, a privately owned boat is stored at the dock and is not available for guest use. Exterior security cameras are present. A security camera monitors the dock area solely for the safety and security of the boat and associated equipment. There is a camera located at the front door. The primary guest making the reservation must be at least 26 years of age.

Sandy Feet Retreat - 5539

Sarasota, FL, US
3 Bedrooms 6 Guests
Sep 1 - 8
$868 night

🌴 Sandy Feet Retreat | Coastal Pool Retreat, Steps to Siesta Key Beach & Village 💖 Why You’ll Love This Home This is the kind of place where shoes come off instantly and the beach becomes part of your daily rhythm. You’re just steps from Siesta Key Beach, yet tucked into a calm residential pocket that feels private, easy, and refreshingly peaceful. Every detail feels intentional, from the high-end coastal décor to the bright, airy layout designed for comfort and connection. Mornings begin with Gulf breezes on the screened lanai, afternoons drift by beside the heated pool and spa with a sun-shelf tanning ledge, and evenings end with glowing Siesta Key sunsets. 👨‍👩‍👧 Perfect For Families, couples, multigenerational groups, and remote workers seeking walkable beach access and relaxed island living. 🎞️ Imagine This Wake to soft sunlight, brew a cup of coffee, and step onto the screened porch as warm island air drifts through. With the beach so close, there’s no rush or planning, just grab a towel and wander down to the sand whenever the mood strikes. Afternoons slow naturally with cool, light-filled interiors and space to truly unwind together. As the sun sets, gather outside again for dinner, watching the sky change colors, already excited for another perfect Siesta Key day. 🛌 Where You’ll Sleep • Bedroom 1: King Bed, Ensuite Bath, TV • Bedroom 2: King Bed, Shared Bath, TV • Bedroom 3: Queen Bed, Shared Bath, TV 📍 Explore the Area • 0.1 Miles to Siesta Key Beach – World-Famous Quartz Sand and Calm Gulf Waters • 0.7 Miles to Siesta Key Village – Restaurants, Live Music, Cafés, and Boutiques • 4.5 Miles to Turtle Beach – Quieter Shoreline and Kayaking Access • 7.3 Miles to Downtown Sarasota – Arts, Waterfront Dining, and Cultural Attractions • 9.8 Miles to St. Armands Circle – Upscale Shopping and Dining • Free Island Trolley Service Makes Getting Around Easy ⌛ Don’t wait—this home books fast. Your reservation includes peace of mind with our CottageClean program, featuring a 6-hour deep clean and 35-point inspection. 🔎 Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. Exterior security cameras are installed at the front door and along both sides of the property for security purposes only. No cameras are located inside the home or in private guest areas.

Majestic Coastal Escape

Siesta Key, FL, US
3 Bedrooms 6 Guests
Aug 18 - 28
$388 night

Welcome to Majestic Coastal Escape – A Luxury Siesta Key Retreat! Step into a world where mid-century sophistication meets coastal serenity. Majestic Coastal Escape is more than just a home; it’s an architectural sanctuary. Featuring a rare triple-King layout, this 2,400 sq. ft. masterpiece boasts vaulted ceilings, exposed beams, and floor-to-ceiling glass that blurs the line between the designer interior and your private tropical oasis—complete with a modern pool and spa. LOCATION HIGHLIGHTS: - Newly renovated mid-century modern home in desirable Siesta Key neighborhood - Short 15-minute walk (0.7 miles) to Siesta Key Beach Access #8 - 1.5 miles to Siesta Key Village for dining, shopping, nightlife, and entertainment - Quiet residential area for privacy and relaxation - Close to powdery white sands and crystal-clear Gulf waters PROPERTY FEATURES: - 3 bedrooms/ 2 bathrooms home (2400+ sq ft) - Private heated pool and spa surrounded by lush tropical greenery (note: pool heat is extra) - Vaulted ceilings, exposed beams, curated artwork, and modern design - Two enclosed lanais for outdoor living and shade - Smart TV with streaming apps, Sonos sound system, high-speed WiFi - Covered carport parking and outdoor BBQ grill LIVING ROOM: - Open-concept living space with floor-to-ceiling glass sliders - Striking decorative stone fireplace - Views of pool and tropical landscaping KITCHEN AND DINING: - Chef’s kitchen with soft-close cabinetry, large farmhouse sink, and high-end appliances - Quartz countertops, ample prep space, and modern finishes - Dining area for 10 guests - Easy access to outdoor lanai for alfresco meals BEDROOMS AND BATHROOMS: - Master bedroom: king bed, en-suite bath, and lanai access - Master ensuite bathroom: spacious vanity, walk-in shower - Second and third bedrooms with king-sized, low-profile beds - Guest bathroom: tub/shower combo with spa styled vanity EXTRA PERKS: - Poolside loungers, multiple seating areas, and outdoor dining for 10 - Screened lanai for shade and privacy - Complimentary beach items provided: a couple of beach chairs, a beach umbrella, and beach towels - Exterior security cameras for added safety LOCAL FAVORITES: -- Siesta Key Beach Access #8 for sunbathing, swimming, and shell-hunting - Sunday night drum circle at the beach - Siesta Key Village for boutique shopping, fine dining, and nightlife - Short drive or free shuttle to the village from the home IMPORTANT INFO: - No pets, no smoking, no parties - Maximum occupancy 6 guests - Pool Heat is optional. Extra fee applies. EXPERIENCE THE BEST OF SIESTA KEY IN THIS LUXURIOUS MID-CENTURY MODERN RETREAT, WHERE RELAXATION AND SOPHISTICATION MEET COASTAL CHARM. IMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Dockside Getaway on Avenida

Siesta Key, FL, US
2 Bedrooms 6 Guests
Aug 23 - 30
$351 night

Welcome to The Dockside Getaway on Siesta Key! A sun-filled, high-end retreat that combines indoor elegance with outdoor bliss. This upscale, canal-access property is perfect for families, seasonal visitors, or couples looking to experience Sarasota’s most iconic island in laid-back luxury. LOCATION HIGHLIGHTS: - Minutes to Siesta Key Village for restaurants, shops, and bars - Short distance to Siesta Key Beach with powder-soft white sand and turquoise water - Quiet residential neighborhood for peaceful escapes - Easy access to canal for boating, paddleboarding, or kayaking PROPERTY FEATURES: - 2 bedroom/ 2-bath canal-access retreat (1300 sq ft) - Private, heated pool with sun shelf and lounge seating, partially fenced yard (note: Pool Heat is extra) - Pet friendly: 1 small dog allowed with prior approval and fee - Covered outdoor lounge with dining, seating, and smart TV - Front patio shaded for coffee or cocktails - Private dock across the street - Washer and dryer - Ring doorbell for added security LIVING ROOM: - Indoor elegant space with high-end furnishings, couch doubles as a sofa bed - Open layout connecting to outdoor lounge - Smart TV and streaming capabilities (just need your log in), dedicated wifi KITCHEN AND DINING: - Fully equipped kitchen with modern appliances - Dining table seats 4 plus 1 more seat at the bar - Access to outdoor dining in covered lounge, seats 6 BEDROOMS AND BATHROOMS: - Master bedroom: king bed, wall-mounted TV and ensuite bathroom - Master ensuite bathroom: walk-in shower and updated vanity - Guest bedroom: queen bed, with work desk - Guest bathroom: walk-in shower, vanity with big mirror EXTRA PERKS: - Complimentary beach items provided: a couple of beach chairs, a beach wagon, beach umbrella and beach towels LOCAL FAVORITES: - Siesta Key Village with shops, bars, and dining - Siesta Key Beach - Nearby outdoor activities like boating, paddleboarding, and kayaking IMPORTANT INFO: - No smoking anywhere on property - No parties or events, please respect the quiet residential neighborhood - Pool heat optional at an extra cost MAKE MEMORIES THAT LAST A LIFETIME ON SIESTA KEY. BOOK YOUR PERFECT VACATION TODAY! All pets must be approved so reach out to us first. Certain properties have weight and breed restrictions. For approved pets, there is an a nonrefundable pet fee of $300 plus taxes and processing fee per pet. Make sure to pick up after your dogs. IMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

The Hideaway (SKLRP)

Siesta Key, FL, US
4 Bedrooms 10 Guests
Aug 21 - 23
$610 night

The Hideaway by Siesta Key Luxury Rental Properties Welcome to The Hideaway, a luxurious private gated retreat featuring four bedrooms and five bathrooms, located less than a 5-minute walk to Siesta Key Beach. This beautifully designed home offers the perfect blend of upscale comfort and relaxed island living, complete with a screened in pool, spacious balconies, an elevator, and high-end finishes throughout. Just steps from Siesta Key Village, this property is ideal for family vacations and extended coastal getaways. Highlights • 3-minute walk to Siesta Key Beach • 4 Bedrooms, 4.5 Bathrooms • 1 King, 2 Queens, 2 Double over Double Bunk Beds • Private Pool in Screened-In Patio • Multiple Balconies • Pool Table and Upstairs Game Room • Elevator • Near Siesta Key Village • 4 Parking Spaces The centerpiece of this elegant home is the expansive screened in outdoor oasis, designed for both relaxation and entertainment. Guests can take a refreshing swim in the private pool, unwind on comfortable loungers, or enjoy meals outdoors with the serene sound of island breezes. The covered patio and screened in surroundings create a peaceful environment protected from sun and insects. Inside, the home’s luxurious features continue with a game room and bar area on the upper level. The elevator adds convenience for all ages, and the private gated entrance enhances the sense of seclusion and comfort. The open concept main living area offers a bright and welcoming setting, seamlessly connecting the living room, dining space, gourmet kitchen, laundry room, and half bath. The living room features a plush sofa and large TV for movie nights, while the modern coastal kitchen boasts high-end appliances and a gas stove designed for preparing meals with ease. Guests can dine casually at the kitchen island or more formally at the dining table. Upstairs, the game room includes a pool table and a stylish bar setup. Sliding glass doors open to a stunning deck with outdoor seating, creating a relaxing spot to enjoy the refreshing island air. The first floor primary bedroom is a serene retreat with a canopy king bed, patio access, pool views, and a luxurious ensuite bathroom featuring a rain shower, standalone soaking tub, and an oversized walk-in closet. On the second floor, two beautifully designed queen bedrooms each feature their own ensuite bathroom with walk-in showers, offering comfort and privacy for guests. The third-floor bedroom is perfect for younger travelers, with two double-over-double bunk beds, a workstation, closet, and a private ensuite bathroom with walk-in shower. Room Details -Primary Bedroom (1st Floor): King bed, patio access, ensuite bathroom with walk-in rain shower and standalone tub -Second Bedroom (2nd Floor): Queen bed, ensuite bathroom with walk-in shower -Third Bedroom (2nd Floor): Queen bed, ensuite bathroom with walk-in shower -Fourth Bedroom (3rd Floor): Two Double-over-Double Bunk Beds, ensuite bathroom with walk-in shower The Hideaway offers a private gated entrance, screened-in pool, game room, bar, elevator, and multiple balconies to enjoy the island atmosphere. Located just one block from Siesta Key Village, guests can easily walk to cafes, boutique shops, restaurants, ice cream spots, and live entertainment. With its luxurious design, private pool, well-appointed kitchen, game room, and prime location near both the beach and Siesta Key Village, The Hideaway by Siesta Key Luxury Rental Properties offers an elevated island retreat perfect for families and groups. Book your stay at The Hideaway today and experience the best of Siesta Key!

Palm Island Canal Home - 4 BR

Siesta Key, FL, US
4 Bedrooms 8 Guests
Aug 18 - 25
$603 night

Welcome to Palm Island Canal Estate! Indulge in the ultimate Siesta Key lifestyle at this breathtaking Spanish Mediterranean custom estate. Nestled in a prestigious, quiet enclave, this 3,500 sq. ft. masterpiece offers a rare combination of canal-front serenity and beachside convenience. Whether you’re launching a kayak from your private backyard or taking a 5-minute stroll to the powdery sands of Beach Access #10, this home is the pinnacle of coastal luxury. The owners cherish this as their family getaway and wish to share it with other families who will treat it with care. THE OUTDOOR OASIS - Private Splash Pool: Refresh in your heated pool (maintained at a perfect 86°F year-round at no extra cost). - Canal-Side Living: Launch your kayaks directly from your backyard and explore the scenic waterways of Siesta Key. - Outdoor Lounging: Multiple screened lanais and seating areas offer the perfect vantage point for morning coffee or sunset cocktails. DESIGNER INTERIORS - Mediterranean Elegance: Custom architecture featuring dark cherry cabinetry, granite countertops, and soaring ceilings. - Coastal Sophistication: Professionally decorated with Tommy Bahama-inspired furnishings and a dedicated wet bar for evening entertaining. - Dining for the Whole Group: Features a formal dining room, a side café nook, and a convenient main-floor powder room for guests. HOME LAYOUT & BEDROOMS - Suite Privacy: The 4-bedroom layout is spread across multiple levels, offering maximum privacy for large groups. - Master Sanctuary (Upper Level): A King suite with private lanai access and a spa-like ensuite featuring a jetted tub and walk-in shower. - King Guest Suite (Mid-Level): A spacious King room with a private ensuite bathroom. - Additional Guest Rooms (Upper Level): One Queen bedroom with balcony access and one Twin bedroom - perfect for kids or extra guests. - Remote Work Den: A dedicated workspace with a desk for those who need to stay connected. PROPERTY FEATURES - Climate & Comfort: Central AC and ceiling fans throughout. - Tech-Ready: Dedicated high-speed WiFi and YouTube TV included. - Parking & Extras: Spacious garage/driveway parking and complimentary beach gear provided. IMPORTANT INFO - Layout Note: This custom home features multiple staircases, which adds to the architectural charm but may not be suitable for those with limited mobility. - Guests must respect family-friendly quiet nature - Pristine Environment: Located in a quiet residential area. Strictly no pets, smoking, or parties. YOUR LUXURY, FAMILY BEACH VACATION STARTS THE MOMENT YOU RESERVE. BOOK PALM ISLAND ESTATE TODAY! IMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Siesta Key Village, Heated Pool, Beach Access 4-min. Walk, 3bdr

Siesta Key, FL, US
3 Bedrooms 10 Guests
Aug 27 - 30
$526 night

Known for its quartz sand and crystal clear waters, the beaches of Siesta Keys are ranked No. 2 in the U.S. and No. 9 globally as one of the best travel destinations in 2024. Siesta Key, a barrier island in the Gulf of Mexico, is less than a 30 min drive from SRQ Airport. This vacation rental is one of a few hand-selected options brought to you by Siesta Key Dreams. With Beach and Village walkability, we are confident that this space will cultivate unforgettable memories. This two-story townhouse style location, Siesta Key Dream’s closest unit to the Village, includes 3 spacious bedrooms that are perfect for up to 10 guests. On the first floor, you’ll experience an open floor plan connecting a welcoming living room, a dining room that seats 6, and kitchen featuring stainless steel appliances. On the second floor, you’ll find three bedrooms and two bathrooms. The main bedroom has an in-room bathroom, tub with jets, and a walkout balcony perfect for a coffee and a read. In the guest room, you’ll see a Juliet balcony that provides fantastic view of the pool below, the keys greenery, and surrounding neighborhoods. This location provides free, high-speed internet & Wi-Fi, multiple HD Televisions equipped with live sports & extension channel options via free streaming services, and electric appliances (fridges, ovens, dishwashers, Keurig-pods, washers/dryers) so you will not miss a beat. If needed, this rental can accommodate up to seven beds, which includes a sofa bed on the first floor & a fold-away bed on the second floor. Outside, you’ll have a shared, heated pool and outdoor space that is perfect to bask in the Florida sun and enjoy a quiet pool day or festive BBQ! The 18 x 26 ft pool is surrounded by an array of palm trees and tropical plants, providing full coverage and privacy from neighbors. On the pool deck, you’ll find multiple chaise lounge chairs, large umbrellas for shade, dining tables, and a BBQ for use. This outdoor space is perfect for relaxing or gatherings with friends and family! Siesta Key Dreams always shows our exact address in our listings, so our guests know exactly how close they truly are to the beach and village. Unplug and explore your surroundings, such as the Siesta Village which is a mere ten steps across the street from you – it is so close, you can often hear live music playing! From cafes to fine dining, local shopping and entertainment, you will certainly find what you need. If you’re looking to soak up the sun and clear waters, the beach access point is less than a 5-minute walk from this property. Easily slip on your sandals and take a brief stroll to experience the brilliant 99% white quartz sand. In addition to the stunning, white quartz sand, the beaches of Siesta Keys offer picnic areas, concession stands, and volleyball courts. The shallow, crystal water and year-round lifeguard protection makes each beach a safe and relaxing escape. Having your property mere minutes away from the ocean means that you will certainly witness breathtaking sunsets. A 3-minute walk from the beach reveals Siesta Village, which offers a wide-range of dining and entertainment options from gourmet donuts, coffee, and seafood to award-winning steakhouses. We recognize that parking can be difficult at times to locate, which is why our rentals come with private, reserved spaces at no additional cost to you. Alternatively, we offer an exclusive upgrade which includes a golf cart rental for easy travel and access to all the top tourist spots around town. The Siesta Key Breeze Trolley also operates on the main roads outside your rental, which is free for all riders and operates 8 AM - 10 PM, seven days a week! Siesta Key Dreams wishes to provide you with "Unreasonable Hospitality” – service at the highest caliber, well above your expectations. As soon as you secure your vacation rental, our team will provide you with clear expectations to help prepare for your stay. If you experience any issues upon arrival, a Guest Experience Manager who lives within the Siesta Keys area will be available at a moment’s notice to assist you. Siesta Key Dreams takes pride in providing professional and personalized services to ensure that your stay is unforgettable. Included within your reservation and rental cost are complimentary bathroom toiletries (shampoo, conditioner, soap), coffee & a Keurig-pods, and your choice of either a bottle of wine, champagne, or sparkling grape juice. To prep for the numerous beach trips, we provide you with towels, beach chairs, umbrellas, and carts to transport your items easily! Traveling with your children? We offer complementary cribs and highchairs available per request! Shortly after you secure your vacation rental, you will receive a link where you can book local services experiences provided by vendors throughout the island. Siesta Key Dreams provides golf-carts to rent and mid-stay services such as cleanings, and linen changes. When available, guests can request flexible booking with early check-in or late check out options. Siesta Key Dreams also offers baggage drop-off prior to your check-in time. You will be able to indicate your preferences in the link you will receive prior to check-in. Guests will receive a Rental Agreement via email that provides common details about our terms and conditions, such as our no-smoking policy. Before you check-in, and just after booking, we require guest verification. At the time of check-in, we place a security deposit hold of $500 on the card on file. You will receive information after booking and the process only takes a couple minutes. This allows us to provide a safe location for our guests, neighbors, and employees. Looking for a larger space? Siesta Key Dreams offers the entire complex to rent.

The Coastal Nest

Siesta Key, FL, US
3 Bedrooms 6 Guests
Aug 18 - Sep 17
$253 night

The Coastal Nest by Tropical Sands Accommodations Welcome to The Coastal Nest, an upscale three-bedroom, two-bath vacation home tucked away in a quiet residential neighborhood of Sarasota. Designed for comfort and longer stays, this inviting retreat offers a relaxed coastal atmosphere, thoughtful amenities, and a convenient island location ideal for guests seeking a peaceful home base near Sarasota’s renowned beaches, dining, and outdoor activities. With flexible stay requirements throughout the year and a layout well suited for couples, families, or seasonal visitors, The Coastal Nest delivers an easygoing Florida lifestyle with all the essentials for a comfortable getaway. Highlights • 3 Bedrooms / 2 Bathrooms • King bed, 2 Queen beds • Washer and dryer • Beach chairs and beach cart • Upscale residential home • Quiet island neighborhood • Flexible stay requirements • 2 Parking spots • Convenient Sarasota location The Coastal Nest is equipped with practical comforts that enhance everyday living. Beach chairs and a beach cart make trips to the shoreline simple and enjoyable, while the washer and dryer add convenience for longer stays. This home’s thoughtful setup makes it especially appealing for guests planning extended visits to the Sarasota area. Inside, the home features a comfortable and welcoming living area designed for relaxing after a day of exploring the coast. The kitchen is well equipped for daily meal preparation and casual dining, offering a functional layout that supports both short and long-term stays. Nearby dining space provides an inviting spot for shared meals, morning coffee, or planning the day ahead. The primary bedroom offers a restful retreat with a king bed and a private ensuite bathroom featuring a walk-in shower. Two additional guest bedrooms are furnished with queen beds and share a hallway bathroom with a shower and tub combination, providing comfort and convenience for guests or family members. Room Details • Primary Bedroom: King bed with ensuite bathroom and walk-in shower • Second Bedroom: Queen bed • Third Bedroom: Queen bed • Hall Bathroom: Full bathroom with shower and tub combination Additional features include beach gear for guest use and in home laundry facilities. Please note that the garage and golf cart are reserved for owner use only. Settle into relaxed island living at The Coastal Nest by Tropical Sands Accommodations. With a comfortable layout, essential amenities, and a prime Sarasota location ideal for seasonal or extended stays, this home is a wonderful place to unwind and enjoy Florida at your own pace. Book your stay today and make The Coastal Nest your next coastal retreat. - This home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. This home requires a minimum 30-night stay in accordance with local city regulations, and shorter stays are not permitted. This property does not allow pets of any kind. 2 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Tropical Sands Accommodations Rental Policies for full details. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Sunkissed Pool Home

Siesta Key, FL, US
3 Bedrooms 6 Guests
Aug 21 - 28
$354 night

Welcome to the Sunkissed Pool Home! A beautifully renovated 3-bedroom, 2.5-bathroom private residence on Siesta Key. This upscale home offers a luxurious retreat with a private, enclosed swimming pool, where a new heater can be added for a fee. Perfect for up to 6 guests, the home is ideally located for beachgoers and vacationers alike. LOCATION HIGHLIGHTS: - Siesta Key private home just 1.4 miles from Siesta Key Beach & Pavilion - 1.8 miles from Siesta Key Village with shops, dining, and entertainment - Close to local beaches, parks, and attractions PROPERTY FEATURES: - Renovated 3-bedroom, 2.5-bathroom home (1800+ sq ft) - Private, enclosed pool with optional heater (heat fee extra) - Garage fits one small vehicle (height restriction 5’11”) - Security camera outside and pool door alarm for safety - WiFi throughout the home - Private washer and dryer - Dog-friendly with prior approval and fee (no aggressive breeds, barkers, or chewers) LIVING ROOM: - Family room with large reclining sofa, smart TV for streaming - Open layout connecting to pool and kitchen KITCHEN AND DINING: - High-end stainless steel kitchen with island - Fully stocked with dishes, cookware, and small appliances - Dining table seats 6, island bar seats 4 BEDROOMS AND BATHROOMS: - Master Suite: King bed, en-suite bath with soaking tub, direct pool access - Second Bedroom: Queen bed with pool access - Third Bedroom: Queen bed - Two full bathrooms and one half-bath: walk-in shower and tub/shower combo EXTRA PERKS: - Beach accessories included: towels, couple of chairs, umbrella - Electric George Foreman grill available LOCAL FAVORITES: - Minutes from Siesta Key Village shops, restaurants, and nightlife - Quick access to Siesta Key beaches and watersports IMPORTANT INFO - Maximum occupancy 6 guests - Dogs allowed with prior approval (pets not allowed in pool) - Non-smoking property (vaping restricted to outdoor designated areas) ENJOY YOUR STAY AT THIS SERENE AND WELL-APPOINTED HOME, WHERE YOU CAN RELAX IN STYLE AND COMFORT. All pets must be approved so reach out to us first. Certain properties have weight and breed restrictions. For approved pets, there is an a nonrefundable pet fee of $300 plus taxes and processing fee per pet. Make sure to pick up after your dogs. IMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Hidden Treasure - 622

Siesta Key, FL, US
4 Bedrooms 8 Guests
Aug 30 - Sep 6
$887 night

Escape to Siesta Key’s Hidden Treasure – A Peaceful, Private Island Retreat Welcome to Siesta Key’s Hidden Treasure, a delightful, tranquil escape offering the perfect balance of comfort and luxury. This charming property features a spacious 2-bedroom, 2-bathroom main house and a detached 2-bedroom, 1-bathroom Casita, ideal for larger groups or families looking for both shared and private spaces. Whether you’re seeking relaxation or adventure, Hidden Treasure has everything you need for an unforgettable getaway. Charming and Comfortable Living Spaces Step inside the main house, where you’ll find a bright and cheerful atmosphere designed to make you feel right at home. The main bedroom serves as a peaceful retreat, complete with a luxurious ensuite bath featuring double sinks, an opulent shower, and a seated dressing vanity. The detached Casita off the screened patio provides a cozy, private getaway with a king bedroom, a twin bedroom with two beds, and a shared full bath. With 2 king beds, 1 queen bed, and 2 twin beds, the home comfortably accommodates up to 8 guests, perfect for families or friends. Fresh linens are provided for your convenience. Outdoor Paradise Awaits The heart of this home lies in the screened pool and patio area, a true backyard oasis. Step through the sliding glass doors into a tropical paradise, featuring a private heated saltwater pool, a hot tub, multiple dining areas, and an elevated sun deck perfect for soaking up the sun. Relax poolside in the spacious courtyard, fire up the grill, or enjoy a meal while basking in the gorgeous island weather. As the day winds down, gather around the fire table for breathtaking sunset views. The Banyan tree with its sprawling roots stands as the centerpiece of the lush, tropical landscape, offering an enchanting atmosphere. Fully Equipped for a Seamless Stay The home provides all the essentials to ensure a stress-free vacation. Brew your favorite coffee using the regular or Keurig coffee maker, prepare meals with the fully equipped kitchen, and enjoy the convenience of a dishwasher, washer/dryer, and other amenities for a hassle-free stay. Ideal Location for Siesta Key Adventure Hidden Treasure offers the perfect location for enjoying all that Siesta Key has to offer. In just minutes, you can sink your toes into the powdery white sands of Siesta Key Beach, renowned for its beauty and serenity. Take a scenic stroll or bike ride to the charming Siesta Key Village, where you’ll find a variety of dining, shopping, and entertainment options. Book Your Escape Today Whether you’re lounging by the pool, exploring the nearby beach, or simply enjoying quality time with loved ones, Hidden Treasure is the perfect place to create lasting memories. Book your stay today and experience the ultimate Siesta Key getaway, where relaxation, comfort, and natural beauty come together. Exclusive Amenities Include: • Private Screened Saltwater Heated Pool • Private Hot Tub • 10 Minute Walk to Siesta Key Village • 15 Minute Walk to Siesta Key Beach • 2 Bedroom Detached Private Guest Quarters • 4 Bedrooms, 3 Full Baths (1 Master Bedroom) • 2 King Bed, 1 Queen Beds, 2 Twin Beds (Sleeps 8) with linens provided • Sun Deck • Outdoor Dining & Lounge area • Private Garage • Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, and Kitchen Essentials Provided • Starter Pack of Toiletry Essentials Included - Shampoo, Conditioner, Hand / Face Soap, Body Lotion, & Makeup Wipes • Starter Pack of Home Essentials Included - Dish Soap, Dish Sponge, Dishwasher Tablets, Laundry Tablets, & Cleaning Wipes • Beach Towels, Chairs, Cooler, & Caddy Provided • Free WiFi & 4 HDTV’s • Gas Grill • Enhanced cleaning protocols provided by our CottageClean Team • Island Shuttle Transportation Available Hidden Treasure can accommodate up to 8 guest with a bedding configuration as follows: Main Cottage: • Bedroom # 1: King Bed (1) - Sleeps: 2 • Bedroom # 2: Queen Bed (1) - Sleeps: 2 Private Casita Guest Quarters: • Bedroom # 3: King Bed (1) - Sleeps: 2 • Bedroom # 4: Twin Beds (2) - Sleeps: 2 We go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol within our CottageClean Program. After our six hour in-depth cleaning of your home, we complete a 35 point property inspection to ensure that you feel tremendously safe and happy with this amazing home. This allows you to vacation worry free regarding the cleanliness of your home and truly relax as soon as you arrive. Our goal is to have you feel like you are walking into a brand new vacation home that no one has ever stayed at before! PLEASE NOTE: There is a 1 rental per 30 day period, per Sarasota, FL ordinance, contact us for more information. Reservation must follow under the accordance of the Sarasota County code regulations. This pool is heated from November 15th to April 15th.

Waters Edge - 5049

Siesta Key, FL, US
3 Bedrooms 8 Guests
Aug 18 - 25
$767 night

"Recently Renovated and a Prime Location: Your Gateway to Siesta Key’s Beauty & Adventure Perfectly positioned just north of Siesta Key Village, Waters Edge is only minutes away from the island’s world-famous Siesta Key Beach, known for its powdery white sand and crystalline waters. Explore the vibrant village, with its eclectic mix of shops, delicious dining spots, and lively entertainment. Whether you’re looking to soak up the sun on the beach, stroll through the village, or enjoy a quiet day by the canal, this home offers the perfect balance of convenience and peace. Luxurious Accommodations: Comfort & Privacy for All Inside, Waters Edge provides a thoughtfully designed floor plan with three beautifully appointed bedrooms, ensuring comfort and privacy for everyone in your group. Master Suite: A tranquil retreat, featuring a king-sized bed, a cozy seating area, and direct access to the lanai. The master en suite is a spa-like haven with an oversized double shower, twin basin vanity, and a private commode, offering ultimate in comfort and relaxation. Second Bedroom: Ideal for couples or additional guests, this room also features a king-sized bed and en suite bathroom. It has direct access to the screened pool area, offering a seamless indoor-outdoor experience. Third Bedroom: Perfect for families or friends, this room boasts double queen beds and easy access to the hall full bath, ensuring ample space and convenience for everyone. With three full bathrooms, the home ensures no shortage of convenience, making it the ideal choice for groups who want both comfort and privacy. The inviting living area is designed with relaxation in mind, featuring plenty of seating to unwind after a day of adventure. The fully equipped gourmet kitchen - a chef’s dream! The large kitchen and dining area make it easy to prepare and enjoy meals together. Exceptional Outdoor Living: Your Private Canal-Front Paradise Waters Edge truly shines with its exceptional outdoor spaces. Step outside and relax in the screened-in private heated pool, perfect for swimming year-round, or enjoy a peaceful moment in the canal-front seating area overlooking the water. For added fun, the shuffleboard will provide hours of friendly competition for guests of all ages. Enjoy a casual BBQ in the backyard, where the ambiance is perfect for creating lasting memories under the stars. Canal-Front Location: With easy access to the Intracoastal Waterway, you’ll have endless opportunities for kayaking, paddleboarding, and simply soaking in the serenity of the water. The canal’s calm waters and peaceful atmosphere will make your stay extra special. Ideal for Long-Term Stays: Comfort & Convenience Await Whether you’re here for a short vacation or an extended stay, Waters Edge is the perfect place to experience Siesta Key. The home’s spacious accommodations, quiet neighborhood, and convenient access to local attractions make it ideal for long-term guests who want to enjoy both privacy and proximity to the best of the island. Book Your Siesta Key Getaway Today Experience Waters Edge—where comfort, luxury, and relaxation come together in a stunning canal-front setting. Whether you’re here to unwind by the pool, explore the natural beauty of Siesta Key, or spend time with loved ones, this home promises an unforgettable vacation. Book your stay today at Waters Edge, and start planning your dream Siesta Key escape! Exclusive Amenities Include: • Screened-In Private Heated Pool: Enjoy year-round relaxation. • BBQ Grill: Perfect for outdoor cookouts and gatherings. • Canal-Front Location: Beautiful views with access to the Intracoastal Waterway. • Shuffleboard: Great for all ages to enjoy. • 3 Bedrooms, 3 Bathrooms: Comfortably sleeps up to 8 guests. • 2 King Beds, 2 Queen Beds, • Close to Siesta Key Village and Beach: Easy access to dining, shopping, and the beach. • Spacious Living and Dining Areas: Perfect for family meals and relaxation. • 10 Minute Walk to Siesta Key Village • 1 mile from Siesta Key Beach • Covered Back Patio • Private 2 Car Garage • Outdoor Dining & Lounge area • Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, and Kitchen Essentials Provided • Starter Pack of Toiletry Essentials Included - Shampoo, Conditioner, Hand / Face Soap, Body Lotion, & Makeup Wipes • Starter Pack of Home Essentials Included - Dish Soap, Dish Sponge, Dishwasher Tablets, Laundry Tablets, & Cleaning Wipes • Beach Towels, Chairs, Cooler, & Caddy Provided • Free WiFi • Enhanced cleaning protocols provided by our CottageClean Team • Island Shuttle Transportation Available • Dog-Friendly with an additional Fee (1 dog up to 25lbs) Waters Edge can accommodate up to 8 guests with a bedding configuration as follows: ● Bedroom # 1: King Bed (1) – Sleeps: 2 ● Bedroom # 2: King Bed (1) – Sleeps: 2 ● Bedroom # 3: Queen Beds (2) – Sleeps: 4 We go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol within our CottageClean Program. After our six hour in-depth cleaning of your home, we complete a 35 point property inspection to ensure that you feel tremendously safe and happy with this amazing home. This allows you to vacation worry free regarding the cleanliness of your home and truly relax as soon as you arrive. Our goal is to have you feel like you are walking into a brand new vacation home that no one has ever stayed at before! PLEASE NOTE: There is a 1 rental per 30 day period, per Sarasota, FL ordinance, contact us for more information. Reservation must follow under the accordance of the Sarasota County code regulations. This pool is heated from November 15th to April 15th."

Bali Hai House - 5041

Siesta Key, FL, US
3 Bedrooms 8 Guests
Aug 18 - 25
$586 night

🌴 Bali Hai House | Canal-Front Home with Private Heated Pool, Near Siesta Key Village 💖 Why You’ll Love This Home Bali Hai House places you on a quiet canal in Siesta Key, offering private waterfront views while remaining close to the island’s most popular spots. Located less than 1 mile to Siesta Key Village and under 1.5 miles to Siesta Key Public Beach Access 2, this three-bedroom retreat balances convenience with a peaceful residential setting. With a screened-in patio, private heated pool, and direct canal access, the outdoor spaces are designed for spending time together while staying connected to the water. 👨‍👩‍👧 Perfect For Families and small groups seeking a waterfront Siesta Key stay with private pool access and proximity to both the beach and village dining. 🎞️ Imagine This Start the morning on the screened patio overlooking the canal as wildlife moves quietly across the water. Brew coffee in the kitchen and plan the day, whether that means heading to Siesta Key Beach for a morning swim or strolling through Siesta Key Village for breakfast and shopping. In the afternoon, return home to cool off in the private pool or stretch out in the hammock while others gather around the outdoor seating area. Cast a fishing line directly from the canal’s edge or simply settle into a quiet moment by the water. As evening approaches, light the fire table and share laughs outdoors, or unwind inside in the comfortable living area before retreating to your private bedroom space. 🛌 Where You’ll Sleep • Bedroom 1: King Bed – Sleeps 2 • Bedroom 2: King Bed – Sleeps 2 • Bedroom 3: King Bed – Sleeps 2 • Living Room: Queen Sleeper Sofa – Sleeps 2 Accommodates up to 8 guests. 📍 Explore The Area • 0.8 Miles to Siesta Key Village - Dining, Boutiques, Coffee Shops, and Live Music • 1.5 Miles to Siesta Key Beach - Wide Sand, Gulf Swimming, and Beach Access • 3.6 Miles to Point of Rocks - Perfect for Snorkeling and Shelling • 5.0 Miles to Downtown Sarasota - Options for Restaurants, Shows, and Nightlife. ⌛ Don’t Wait Your reservation includes peace of mind through our CottageClean™ program, featuring a six-hour deep clean followed by a detailed 35-point inspection prior to arrival. 🔎 Need to Know Per Sarasota ordinance, this property is limited to one rental per 30-day period. Reservations must comply with Sarasota County regulations. The pool is heated from November 15th to April 15th. During cooler weather, heating performance may vary depending on outdoor temperatures. Exterior security cameras are installed at the front and rear of the home for security purposes only. No cameras are located inside the home or directed toward private guest areas.

Siesta Key Village, Heated Pool, Beach Access 4-min. Walk, 3bdr

Siesta Key, FL, US
3 Bedrooms 10 Guests
Sep 2 - 5
$521 night

Known for its quartz sand and crystal clear waters, the beaches of Siesta Keys are ranked No. 2 in the U.S. and No. 9 globally as one of the best travel destinations in 2024. Siesta Key, a barrier island in the Gulf of Mexico, is less than a 30 min drive from SRQ Airport. This vacation rental is one of a few hand-selected options brought to you by Siesta Key Dreams. With Beach and Village walkability, we are confident that this space will cultivate unforgettable memories. This two-story townhouse style location, Siesta Key Dream’s closest unit to the Village, includes 3 spacious bedrooms that are perfect for up to 10 guests. On the first floor, you’ll experience an open floor plan connecting a welcoming living room, a dining room that seats 6, and kitchen featuring stainless steel appliances. On the second floor, you’ll find three bedrooms and two bathrooms. The main bedroom has an in-room bathroom, tub with jets, and a walkout balcony perfect for a coffee and a read. In the guest room, you’ll see a Juliet balcony that provides fantastic view of the pool below, the keys greenery, and surrounding neighborhoods. This location provides free, high-speed internet & Wi-Fi, multiple HD Televisions equipped with live sports & extension channel options via free streaming services, and electric appliances (fridges, ovens, dishwashers, Keurig-pods, washers/dryers) so you will not miss a beat. If needed, this rental can accommodate up to seven beds, which includes a sofa bed on the first floor & a fold-away bed on the second floor. Outside, you’ll have a shared, heated pool and outdoor space that is perfect to bask in the Florida sun and enjoy a quiet pool day or festive BBQ! The 18 x 26 ft pool is surrounded by an array of palm trees and tropical plants, providing full coverage and privacy from neighbors. On the pool deck, you’ll find multiple chaise lounge chairs, large umbrellas for shade, dining tables, and a BBQ for use. This outdoor space is perfect for relaxing or gatherings with friends and family! Siesta Key Dreams always shows our exact address in our listings, so our guests know exactly how close they truly are to the beach and village. Unplug and explore your surroundings, such as the Siesta Village which is a mere ten steps across the street from you – it is so close, you can often hear live music playing! From cafes to fine dining, local shopping and entertainment, you will certainly find what you need. If you’re looking to soak up the sun and clear waters, the beach access point is less than a 5-minute walk from this property. Easily slip on your sandals and take a brief stroll to experience the brilliant 99% white quartz sand. In addition to the stunning, white quartz sand, the beaches of Siesta Keys offer picnic areas, concession stands, and volleyball courts. The shallow, crystal water and year-round lifeguard protection makes each beach a safe and relaxing escape. Having your property mere minutes away from the ocean means that you will certainly witness breathtaking sunsets. A 3-minute walk from the beach reveals Siesta Village, which offers a wide-range of dining and entertainment options from gourmet donuts, coffee, and seafood to award-winning steakhouses. We recognize that parking can be difficult at times to locate, which is why our rentals come with private, reserved spaces at no additional cost to you. Alternatively, we offer an exclusive upgrade which includes a golf cart rental for easy travel and access to all the top tourist spots around town. The Siesta Key Breeze Trolley also operates on the main roads outside your rental, which is free for all riders and operates 8 AM - 10 PM, seven days a week! Siesta Key Dreams wishes to provide you with "Unreasonable Hospitality” – service at the highest caliber, well above your expectations. As soon as you secure your vacation rental, our team will provide you with clear expectations to help prepare for your stay. If you experience any issues upon arrival, a Guest Experience Manager who lives within the Siesta Keys area will be available at a moment’s notice to assist you. Siesta Key Dreams takes pride in providing professional and personalized services to ensure that your stay is unforgettable. Included within your reservation and rental cost are complimentary bathroom toiletries (shampoo, conditioner, soap), coffee & a Keurig-pods, and your choice of either a bottle of wine, champagne, or sparkling grape juice. To prep for the numerous beach trips, we provide you with towels, beach chairs, umbrellas, and carts to transport your items easily! Traveling with your children? We offer complementary cribs and highchairs available per request! Shortly after you secure your vacation rental, you will receive a link where you can book local services experiences provided by vendors throughout the island. Siesta Key Dreams provides golf-carts to rent and mid-stay services such as cleanings, and linen changes. When available, guests can request flexible booking with early check-in or late check out options. Siesta Key Dreams also offers baggage drop-off prior to your check-in time. You will be able to indicate your preferences in the link you will receive prior to check-in. Guests will receive a Rental Agreement via email that provides common details about our terms and conditions, such as our no-smoking policy. Before you check-in, and just after booking, we require guest verification. At the time of check-in, we place a security deposit hold of $500 on the card on file. You will receive information after booking and the process only takes a couple minutes. This allows us to provide a safe location for our guests, neighbors, and employees. Looking for a larger space? Siesta Key Dreams offers the entire complex to rent.

Shaker of Salt

Sarasota, FL, US
7 Bedrooms 19 Guests
Aug 22 - 25
$1,586 night

Vunique Vacations was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. Looking for your Lost Shaker of Salt? Well, you’ve found it in this luxury rental home on Siesta Key that pays homage to the late, great Jimmy Buffet and the theme behind his music - paradise, good vibes, and of course great cocktails with better friends! This home is a dream, with outdoor covered patios, balconies, pool area, private sand volleyball court, and entertainment spaces, you’ll have it all! Ya, you read that right, there is a sand volleyball court! You can search, but you won’t find another home like this anywhere in Southwest Florida. It’s truly unique! Woven around the volleyball court you’ll find a beautiful lagoon style pool and spa, with a waterslide, beach entry, and large sun shelves with bubblers and lights! The covered patio is a real outdoor living space with a real tiki bar, 3-large smart TV’s, outdoor grill (natural gas), and multiple dining and lounging options. These spaces are all within the fenced in backyard that borders Sabal Lake and provides privacy and security making it family friendly and perfect for the home’s pet friendly policy (fees and restrictions apply). Sabal Lake is fed directly from Sarasota Bay and provides a peaceful wildlife estuary full of mangroves, birds, and fish for you to enjoy. When you enter this home with 4,100 square feet interior living space, you’ll notice the elevator with service to all floors (except the rooftop), and the fact that this home was purposefully designed to provide the best vacation possible! It has 7 bedrooms (all with en suite baths) and 7 full baths and 2 half baths. There are a total of 6 king beds and 2 sets of king over king bunk beds that comfortably sleep 19 people in beds. The great room is set up as the perfect gathering space as it includes the kitchen, living, and dining areas of the home. The kitchen is a fully stocked kitchen, and we mean that because we know how important it is to you, our valued guests! Not only is it stocked, but it’s also stocked with the products and manufacturers you trust. Additionally, this home features a club room or secondary living space with smart TV, gaming consoles, wet bar with bar top seating, and access to a balcony and the rooftop deck. There are 2 balconies off the great room and club room spaces, the rear balconies overlook the pool and lake, and the front balconies overlook South Siesta Village. Floor Plan Description (by level): Ground Level: Free parking for up to 6 vehicles (2 covered spaces, and 4 spaces in the driveway). On this ground level you’ll find the fully fenced backyard area (pet friendly - fees and restrictions apply), including the sand volleyball court, pool, and covered patio space. This entire area, as previously described, is unmatched! And again, just a reminder, you have a private volleyball court all to yourself! The home’s beach equipment can be found in the garage, which includes 2 beach wagons, 2 coolers, 6 beach chairs, and 4 bikes. We include a full refrigerator and freezer here as well so your beach prep and breakdown, and your use of the home and pool is that much easier. These appliances can also be used to support your pool days and time at home as well. You’ll also access the home’s main entrance foyer with elevator and stair access to the home’s 2 living levels above. The First Level of Living (2nd Floor): This level features a great room with the fully stocked kitchen that includes a cooktop, wall mounted double ovens, full sized refrigerator (with ice maker) and freezer, double dishwashers, double trash/recycling, microwave, toaster, coffee maker, and is very well appointed with cookware, bakeware, dishware, cutlery, and specialty items like crockpots, blenders, and more. If you have any questions on kitchen supplies, our reservationists would be happy to provide more details. The living area is very accommodating, and the dining area seats 16 people comfortably - dining table for 10 and bar seating for 6. There are also 2 balconies on this level, with the rear balcony providing additional dining and seating options directly off the great room. There are 3 bedrooms on this floor including the master bedroom. The master features water views, a king bed, walk-in closet, and an oversized en-suite bathroom with double vanity, a large walk-in shower offering dual shower heads and a free-standing bathtub, and a private water closet. Bedroom 2 (water views) and bedroom 3 both feature king beds and an en-suite bathroom with vanity and walk-in shower. Also located on this floor is a half bath and laundry room with 2 stackable washer/dryer units. The Second Level of Living (3rd Floor): The club room is a secondary living space with comfy couches and large smart TV, wet bar with beverage fridge, bar top seating for 4, and a half bath. The club room houses Nintendo Switch gaming console. It has balcony access with views of the lake and village area and provides stair access to the rooftop deck. There are also 4 bedrooms on this floor. Bedrooms 4 (water view), 5 and 6 all feature a king bed and an en-suite bathroom with vanity and walk-in shower. Bedroom 7 features 2-sets of custom-built king over king bunk beds, seating, and an en-suite bathroom with a vanity and shower/bathtub combo! The Rooftop Deck: This rooftop space provides seating and beautiful views of the Gulf of Mexico, sunset, and treetop views over Siesta Key. It’s perfect for enjoying sunrise over the South Siesta Key Village, or sunset over the Gulf of Mexico, so be sure to grab a book, a coffee or cocktail, and enjoy the sea breeze and Florida sun from this amazing perch overlooking all of Siesta Key. https://www.youtube.com/watch?v=3nKXcGLWoik This home is located in the South Siesta Village entertainment district. You’re next to all the restaurants, entertainment, shopping, markets, marina, and so much more! This super fun entertainment district is a guest favorite! But, even with this proximity, we’ve designed this luxury rental home so that you still have your own privacy. It’s the perfect mix of fun when you want it, and quiet when you need it. You’re also within 1 block from the world-famous Siesta Key Beach (Beach Access 12), so walkability here is maxed at 100%! If you want to explore further, without the hassle of driving, you’ll find multiple stops nearby for the free trolley that provides transportation service to the entirety of Siesta Key. You’re also just a quick drive or Uber/Lyft to the mainland Sarasota area (5 minutes) and downtown Sarasota (20-25 min) for access to the Sarasota’s Performing Arts scene, and numerous fantastic restaurants, shops, marinas, bars and entertainment, grocers, and more. And, day trips to Lido Key, Anna Maria Island, Venice Beach (shark tooth hunting), Myakka State Park and so much more are all less than an hour away, as well as the amazing theme parks of Tampa and Orlando that are all just 1-2 hours away! This Siesta Key luxury vacation rental features Smart TVs with cable and streaming services, as well as Free Wi-Fi throughout the property - including the outside areas for complete coverage for all your work or personal needs. TVs in all bedrooms. Accessibility - in addition to the home’s elevator access to all levels, most doorways and walkways are 30 inches or larger and walk-in showers featured in most bathrooms. Please see the Photos, 3D Tour, & Video for this home for exact information. *Don’t forget to check out our Matterport 3D Tour for this home* And, if you still have any questions concerning our homes, rates, availability calendar, amenities, policies, or otherwise, please contact our team of professional reservationists and we will be happy to assist you. We want you to fully understand what you are booking, and yes, an actual human team member is available to help! You are just a couple of clicks away from paradise!

Paradise Palms!

Siesta Key, FL, US
3 Bedrooms 8 Guests
Aug 18 - 25
$368 night

Welcome to Paradise Palms, a freshly updated three-bedroom sanctuary where island peace meets modern comfort. Tucked away in a quiet residential pocket just minutes from the world-famous white sands of Siesta Key Beach, this home offers the perfect blend of privacy and proximity. Featuring a sparkling screened-in pool and two spacious living areas, it’s a premier choice for families or small groups looking to experience the best of the Gulf Coast. The Highlights - Private Screened-In Pool: Your own tropical oasis for sun-soaked afternoons. - Prime Location: Less than 1.5 miles to Siesta Key Beach access. - Recreation Ready: Ping pong and air hockey tables, plus board games, puzzles, and books. - Beach Gear Included: We provide beach chairs and a beach cart to make your shore days effortless. - Open-Concept Living: Two distinct living rooms with vaulted ceilings and skylights. - Al Fresco Living: Screened lanai with BBQ grill, outdoor dining, and lounge seating. The Living Space The interior of Paradise Palms is designed for relaxation. The bright, airy layout features two separate living rooms, offering plenty of space for the group to spread out. One living area serves as a cozy media room with a large flat-screen TV and direct pool access, while the second boasts soaring vaulted ceilings and coastal decor. Perfect for a quiet morning coffee or evening cocktails! The fully equipped kitchen features modern appliances and bar seating for casual snacks. For family dinners, the formal dining area comfortably seats eight, ensuring everyone has a spot at the table. Bedrooms & Bathrooms - Primary Suite: A true retreat featuring a King bed, private sitting area, and an ensuite bathroom with a walk-in shower. Sliding glass doors lead you directly from your bedroom to the pool deck. - Bedroom 2: Features a comfortable Queen bed and easy access to the hall bath. - Bedroom 3: Perfect for kids or additional guests with a Full bed. - Extra Sleeping: A Queen sleeper sofa in the living room provides flexibility for larger groups. Outdoor Oasis - Step through the sliding doors into your private screened-in lanai. Surrounded by lush tropical landscaping, the pool area is designed for the Florida lifestyle. - Fire up the BBQ grill for a poolside cookout, dine at the outdoor table, or challenge the family to a tournament on the ping pong and air hockey table. Essential Amenities - High-Speed Wi-Fi & Smart TVs for streaming. - Full-Sized Washer & Dryer inside the home. - Parking: Space for up to 4 vehicles (No overnight street parking allowed). - Pet Policy: We are dog-friendly with prior approval and fee! The Neighborhood Paradise Palms is situated in a peaceful residential neighborhood. To maintain the tranquility of our community, we ask all guests to observe local noise ordinances and be respectful neighbors. You are just a short drive or bike ride away from the vibrant Siesta Key Village, local boutiques, and the breathtaking sunset views of the Gulf. Other information: - No smoking property - Pool heat extra - reach out for details. - No parties or large gatherings - This home is in a quiet residential neighborhood. We kindly ask that all guests treat the home and surrounding community with the same care and respect as they would their own. - Per Sarasota ordinance, this rental is limited to 1 rental per 30 day period. Ready to soak up the sun? Book your stay at Paradise Palms today! All pets must be approved so reach out to us first. Certain properties have weight and breed restrictions. For approved pets, there is an a nonrefundable pet fee of $300 plus taxes and processing fee per pet. Make sure to pick up after your dogs. IMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Vacation Rentals in Siesta Key by Amenities & Features

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Vacation Rentals Near Siesta Key

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