Vacation rentals in South Sarasota, FL with a pool

Explore 151 vacation rentals, homes, and villas with pools in South Sarasota, 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 $77 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.

151 Homes with Pools in South Sarasota

Sleeps 6 • Private Pool • Fire Pit • Game House

Sarasota, FL, US
3 Bedrooms 8 Guests
Aug 24 - 26
$184 night

This 3-bedroom home is in a prime location & has EVERYTHING you need for an amazing vacation in Sarasota, FL! • Private Pool • Fire Pit • Outdoor Patio/Dining • BBQ Grill • Game House: Ping Pong Table, Basketball Hoops, 1 Child and 2 Adult Bikes! • Den w/ Smart TV & Dedicated Workspace • Fully Stocked Kitchen • Drip Coffee Maker • Plush Beds • High Speed WIFI • Family Friendly - High Chair & Pack ’n Play • Dog Friendly • Ample Parking • Washer & Dryer Pack your bags and bring the whole crew—this 3-bedroom, 2-bathroom home sleeps up to 8 guests and is designed for both relaxation and fun. Start your mornings with a splash in the private pool, lounge on the patio, or wind down by the firepit under the stars. Feeling playful? Head to the indoor game room for a round of ping pong or grab the bikes and cruise around the neighborhood like a local. Conveniently located, our home offers easy access to nearby attractions, shopping, and dining options. Whether you’re here for sunny pool days, cozy nights by the fire, or friendly game competitions, this home has all the right vibes for an unforgettable Sarasota getaway! MAIN SPACES OF THE HOME: – 3 BEDROOMS & 2 BATHROOMS– BEDROOM 1: * King-sized Bed * Smart TV * Nightstand and Lamps * Dedicated Workspace * Cozy Seating * Ensuite Bathroom BEDROOM 2: * Queen-sized Bed * Nightstand and Lamp * Ceiling Fan * Closet BEDROOM 3: * King-sized Bed * Nightstand and Lamp * Dresser w/ Mirror * Ceiling Fan – 2 BATHROOMS – * Ensuite Bathroom with Walk-in Shower * Full Bathroom with Shower/Tub Combo – CHEF’S KITCHEN – * Fully Stocked * High-end Appliances * Large Refrigerator * Ample Cabinetry & Cooking Space * Coffee Maker: Drip – LIVING ROOM – * Smart TV * Sofa Bed (Queen) * Ceiling Fan * Open Floor Plan – GAME ROOM – * Ping Pong Table * Basketball Hoops * 1 Child & 2 Adult Bikes * Full-sized Fridge * Beach Essentials: Pool Toys, Coolers, and Beach Gear – OUTDOOR FUN & AMENITIES – * Private Pool * Fire Pit * Outdoor Patio/Dining * BBQ Grill The guest has access to the entire home minus the locked cleaners’ closet. By Car: Renting a car is a convenient option to explore the area at your own pace. Having a car makes it easy to visit the many shopping centers, restaurants, and other points of interest in the area. Rideshare Services: Services like Uber and Lyft are readily available in the area, providing a convenient alternative to driving. Simply book a ride through the app, and you’ll be on your way to your destination in no time. Check-in is at 4pm Check-out is at 10am - Up to 2 dogs are allowed for $125 per stay, no cats please. We kindly ask that your dog is crate trained and that you pick up after your dog. - No parties allowed—violations may result in immediate termination of the stay. We aim to maintain a respectful environment for our neighbors. - Parking in the driveway with a carport for 5 cars max. Street parking allowed: NO - If you’re interested in a long-term stay, please reach out to inquire about availability. - Guests must be 25 years or older to book this property. GUEST VERIFICATION: To help ensure a smooth and secure stay for all guests, the primary guest listed on the reservation may be asked to complete a quick verification process within 48 hours of booking, depending on the platform used to book the reservation. Prior to check-in, guests may also be asked to sign a Rental Agreement that includes agreeing to our rental terms and conditions and, on certain booking platforms, providing a valid government-issued ID and matching credit card before arrival. Included with your booking is our damage waiver coverage, which helps protect against accidental, self-reported damage during your stay when reported prior to check-out.

The Coastal Nest

Siesta Key, FL, US
3 Bedrooms 6 Guests
Aug 24 - Sep 23
$184 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.

Sarasota Waterfront Escape: Private Pool & Views!

South Sarasota, FL, US
5 Bedrooms 12 Guests
Aug 29 - Sep 28
$235 night

Canal Views & Picturesque Sunsets | 5 Mi to Siesta Key | Snowbirds & Remote Workers Welcome Whether you're seeking a peaceful escape or an adventurous getaway, you'll find that this 5-bedroom, 3-bath vacation rental has everything you need for your extended stay in Sarasota. Take a refreshing dip in the private pool, make sandcastles on nearby beaches, and enjoy an afternoon picnic at Bayfront Park. As the sun sets, come home for dinner and a cozy movie night with your crew. Book today! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed, 1 full sleeper sofa - Bedroom 2: 1 queen bed - Bedroom 3: 1 full bed - Bedroom 4: 1 twin bed w/ 1 twin trundle - Bedroom 5: 1 queen sleeper sofa MAIN FEATURES - Smart TV - Dining tables - Private boat dock - Screened-in lanai w/ private pool (not heated) - Spacious yard KITCHEN - Refrigerator, stove/oven, dishwasher, microwave - Drip coffee maker (bring your own coffee) - Cooking basics, dishware/flatware GENERAL - Free WiFi - Central A/C & heating, ceiling fans - Linens & towels, trash bags & paper towels - Complimentary toiletries - Washer/dryer FAQ - 2 exterior security cameras (facing out) - Quiet hours (after 11:00 PM) ACCESSIBILITY - Single-story home, 1 small step required to enter PARKING - Garage (1 vehicle) - Driveway (2 vehicles) -- THE LOCATION -- - 4 miles to Siesta Beach, 9 miles to Lido Key Beach, 13 miles to Nokomis Public Beach & 15 miles to Venice Beach - 5 miles to Sarasota Art Museum & 10 miles to The John and Mable Ringling Museum of Art - 6 miles to Bayfront Park - 9 miles to Sarasota Jungle Gardens - 10 miles to Mote Marine Laboratory & Aquarium - 10 miles to Sarasota Bradenton International Airport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $75 fee (+ fees & taxes, max 1 pet) - No events, parties, or large gatherings - Must be at least 25 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in - Please observe quiet hours after 11:00 PM ADDITIONAL INFORMATION - Your safety matters. This property features 2 exterior security cameras. Camera 1 is on the front of the house facing the entryway, and camera 2 is on the back of the house facing the lanai and backyard. The cameras are outward facing and do not look into any interior spaces. They actively record video and audio while guests are in the residence - This single-story home requires 1 small step to enter

Casamigos - 1805

Sarasota, FL, US
5 Bedrooms 10 Guests
Aug 30 - Sep 6
$482 night

🌴 Casamigos | Heated Saltwater Pool & Tiki Bar 💖 Why You’ll Love This Home Experience island elegance at Casamigos, a tropical oasis designed for memorable gatherings. From a private heated saltwater pool to an authentic 8-seat tiki bar, every detail invites you to unwind in style. This upscale retreat blends vibrant West Indies charm with modern luxury—ideal for creating lasting vacation memories. 👨‍👩‍👧 Perfect For Multi-generational families, friend groups, and anyone seeking a stylish, spacious getaway near Siesta Key’s best beaches and dining. 🎞️ Imagine This Imagine waking to the soft Florida sun filtering through towering palms as you step into an airy living room with 12-foot ceilings and cool coastal breezes. Hear the gentle splash of the heated pool just beyond sliding glass doors, where the scent of bougainvillea mingles with fresh breakfast from the gourmet kitchen. In the afternoon, enjoy a fresh panini from the provided press and unwind with a glass of wine from the wine fridge. In the evening, gather with friends at the tiki bar under twinkling lights, sharing cocktails and laughter surrounded by lush tropical blooms and complete privacy. 🛌 Where You’ll Sleep • Bedroom 1: King Bed, Ensuite Bath, TV • Bedroom 2: King Bed, Hall Bath, TV • Bedroom 3: King Bed, Hall Bath, TV • Bedroom 4: King Bed, Hall Bath, TV • Bedroom 5: 2 Twin Beds, Shared Bath 📍 Explore the Area • 3.4 Miles to Siesta Key Village, Full of Shops, Cafes, and Nightlife • 4.5 Miles to Siesta Key Beach, Famous for its Powdery White Sand • 2.2 Miles to Downtown Sarasota, Dining, Shopping, Parks • 5.5 Miles to Lido Key’s Beaches and Restaurants ⌛ 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 are provided for a seamless first couple of nights. Free high-speed WiFi included. The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. Please inquire if any guests require stair-free access. This property is registered as a vacation rental with the City of Sarasota with a Registration Number of VR25-00068 Due to City of Sarasota vacation rental code, this property must be rented once during a seven (7) day period and have a maximum occupancy of 10 guests. The primary guest making the reservation must be at least 26 years of age.

Ventana Rosa - 1905

Sarasota, FL, US
3 Bedrooms 8 Guests
Aug 25 - Sep 1
$272 night

🌴 Ventana Rosa | Heated Pool + Lush Tropical Outdoor Living 💖 Why You’ll Love This Home Wrapped in tropical foliage and designer touches, Ventana Rosa is a beautifully renovated Sarasota retreat with a private heated pool, lush outdoor space, and thoughtfully styled interiors. Just minutes from Siesta Key Beach, it offers a seamless indoor-outdoor flow for families or groups to reconnect and unwind in comfort. 👨‍👩‍👧 Perfect For Ideal for families, friend groups, and remote work escapes looking for a serene, upscale home base with easy access to Siesta Key and downtown Sarasota. 🎞️ Imagine This Start your morning on the shaded poolside terrace, sunlight flickering through palm fronds. The kids splash in the heated pool while you prepare brunch in the gourmet kitchen stocked with modern appliances and bright quartz counters. After a beach day just minutes away, rinse off in the outdoor shower, fire up the gas grill for dinner, and share stories beneath string lights in your private tropical hideaway. End the evening curled up on the sofa, planning tomorrow’s adventures on Florida’s Gulf Coast. 🛌 Where You’ll Sleep • Bedroom 1: King Bed, En-Suite Bath with Walk-In Shower, TV • Bedroom 2: King Bed, Shared Bath, TV • Bedroom 3: Queen Bed + 2 Twin Beds, Shared Bath, TV • Living Room: Sleeper Sofa (Queen), Ground Floor 📍 Explore the Area • 1.7 miles to Siesta Key Beach – world-famous quartz sand and turquoise water • 1.5 miles to Siesta Key Village – boutiques, dining, nightlife • 4.8 miles to Downtown Sarasota – arts, shopping, and cultural attractions • Surrounded by walkable neighborhoods, local parks, and island energy ⌛ Don’t Wait—This Home Books Fast Your stay includes peace of mind with our CottageClean™ program, featuring a 6-hour deep clean and 35-point inspection before your arrival. Starter packs of kitchen and toiletry essentials are included for a seamless first few nights. Free High-Speed WiFi is provided throughout the home. 📝 Need to Know: This is a single level home. The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. This property is registered as a vacation rental with the City of Sarasota with Registration Number VR25-00069.

Siesta Sun Oasis - 5545

Sarasota, FL, US
5 Bedrooms 10 Guests
Aug 28 - Sep 4
$815 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.

The Sun Dial - 827

Siesta Key, FL, US
4 Bedrooms 12 Guests
Aug 26 - Sep 2
$662 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.

Hidden Treasure - 622

Siesta Key, FL, US
4 Bedrooms 8 Guests
Aug 30 - Sep 6
$782 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.

Sunkissed Pool Home

Siesta Key, FL, US
3 Bedrooms 6 Guests
Aug 24 - 31
$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.

Sunburst Courtyard - 430

Siesta Key, FL, US
4 Bedrooms 12 Guests
Oct 31 - Nov 28
$875 night

Welcome to Sunburst Courtyard, your waterfront paradise located on the tropical island of Siesta Key! This exceptional 4-bedroom, 3-bathroom rental home offers all the amenities you need for a memorable stay, and its prime location provides easy access to the world-famous Siesta Key Beach, just a 15-minute walk away. As you enter Sunburst Courtyard, you’ll be greeted by the mother-in-law suite, providing a private and comfortable space for guests or extended family members. Moving through the property, you’ll discover the centerpiece of this home - the spacious screened-in courtyard, featuring a sparkling private heated pool & spa and ample lounging areas. Spend your days swimming, relaxing poolside, or grilling out and enjoying delicious BBQ meals in the warm island breeze. The main house of Sunburst Courtyard features two bedrooms and two baths, offering a comfortable and inviting space to unwind. The bright and elegant design creates a welcoming atmosphere, while the private casita adjacent to the courtyard provides two additional generously sized bedrooms, ensuring privacy and space for everyone in your group. Inside the main living quarters, the fully equipped gourmet kitchen is a chef’s dream, featuring top-of-the-line appliances, sleek countertops, wood cabinets, and ample space to create culinary masterpieces. Whether you’re whipping up a quick breakfast or preparing a gourmet feast, this kitchen has everything you need. Adjacent to the kitchen is the inviting living area, complete with comfortable seating and a pool table for hours of entertainment and friendly competition. The living room features a screened-in balcony, perfect for those looking to unwind in the shade while still taking in the breathtaking water views. As you make your way to the backyard, you’ll find a tranquil retreat where you can soak up the sun, sip your favorite beverage, and take in the picturesque surroundings. From the comfort of your own backyard, you can marvel at the beauty of the water and immerse yourself in the peacefulness of the outdoors. Sunburst Courtyard is ideally located, allowing you to experience the best of Siesta Key. Take a leisurely 10-minute walk to Siesta Key Village, where you can explore a variety of dining options, indulge in some retail therapy, and immerse yourself in the vibrant local entertainment scene. For beach lovers, a scenic 15-minute stroll will lead you to the pristine white sands and crystal-clear waters of Siesta Key Beach, consistently ranked among the top beaches in the world. Exclusive Amenities Include: • Private Screened Heated Pool & Spa • Pool Table • 10 Minute Walk to Siesta Key Village • 15 Minute Walk to Siesta Key Beach • Canal Front Home • 2 Bedroom Detached Private Guest Quarters • 4 Bedrooms, 3 Full Baths • 2 King Beds, 1 Queen Bed, 1 Twin Bed w/ Trundle Bed (convertible to a King), 1 Queen Sleeper Sofa, 2 Rollaway Twin Beds (Sleeps 12) with Linens Provided • Private Courtyard Lounge Area • Private 2 Car 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 & Multiple HDTV’s • Gas Grill • Enhanced Cleaning Protocols Provided By Our CottageClean Team • Island Shuttle Transportation Available ​​​​​​​• Dog-Friendly with a Fee (1 dog up to 25lbs) Sunburst Courtyard can accommodate up to 12 guest with a bedding configuration as follows: Main Cottage: • Bedroom # 1: King Bed (1) - Sleeps: 2 • Bedroom # 2: Queen Bed (1) - Sleeps: 2 Private Guest Quarters: • Bedroom # 3: King Bed (1) - Sleeps: 2 • Bedroom # 4: Twin Bed w/ Trundle Bed (convertible to a King) (1) - Sleeps: 2 • Common Space: Queen Sleeper Sofa (1) - Sleeps: 2 • Extra: Twin Rollaway 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. 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. We happily welcome up to 2 small dogs (up to 25 lbs) with a $250 fee per pet—breed guidelines apply to ensure a safe and comfortable stay for everyone.

Mainsail Vacation Rental

Siesta Key, FL, US
4 Bedrooms 10 Guests
Dec 31 - Jan 5
$2,149 night

Mainsail by Siesta Key Luxury Rental Properties Mainsail by Siesta Key Luxury Rental Properties is a breathtaking 4 bedroom, 3 and a half bath waterfront luxury home with a bonus room, private dock, and spectacular Intracoastal Waterway views. Nestled at the end of a quiet street and just a 10-minute walk to Crescent Beach, this upscale retreat offers a refined yet relaxed coastal lifestyle perfect for large families and groups. With a private pool, in-ground spa, multiple outdoor lounges, and seamless indoor and outdoor living. Mainsail sets the stage for an unforgettable Siesta Key luxury rental experience near South Siesta Key Village. Highlights • 10-minute walk to Crescent Beach • 4 Bedrooms / 3.5 Bathrooms • 3 King beds, 2 Queens • Private dock (18 ft) • Private heated pool and in-ground spa • 2 kayaks included • Outdoor bar and outdoor kitchen • Covered outdoor dining and lounge areas • Wet bar and wine fridge • 5 parking spaces Designed for waterfront relaxation, Mainsail features a private heated pool, a spa, and wide poolside terraces capturing panoramic waterway views. Enjoy evening cocktails at the outdoor bar, prepare meals in the covered outdoor kitchen, or gather for sunset dining on the balcony overlooking the Intracoastal. With two kayaks included, guests can explore the calm waterway right from the private dock. Every outdoor space is crafted for comfort, inviting you to unwind in a true tropical outdoor oasis. Inside, Mainsail offers a bright and expansive open concept layout with designer inspired coastal interiors. Floor to ceiling windows frame sparkling water views throughout the living and dining areas, while the gourmet kitchen features high end appliances, generous counter space, and island seating ideal for group gatherings. The dining table seats nine comfortably for shared meals, and an additional wet bar with a wine fridge enhances the luxury entertaining experience. Multiple lounge areas, and beautiful hardwood floors throughout, create a warm, elevated atmosphere. Retreat to the luxurious second-floor primary suite, complete with a California king bed, ensuite bathroom, double vanity, walk-in shower, and walk-in closet, plus a convenient mini refrigerator. On the main floor, two guest suites offer king beds and private ensuite bathrooms, one with a shower/tub combination and one with a walk-in shower. A fourth bedroom includes two queen beds, making it ideal for families or additional guests. The bonus room features a twin daybed, offering a space for relaxing or flexible use. All rooms are designed with calming coastal finishes to ensure a restful stay. Room Details -Primary Bedroom (2nd floor): King bed, ensuite bathroom with double vanity + walk-in shower -Second Bedroom (1st floor): King bed, ensuite bathroom with shower/tub combo -Third Bedroom (1st floor): King bed, ensuite bathroom with walk-in shower -Fourth Bedroom (1st floor): Two Queen beds This home includes a private dock, kayaks, outdoor bar, outdoor kitchen, multiple waterfront terraces, balcony seating, covered lounges, wet bar, and extensive space for up to five vehicles. Located near South Siesta Key Village, guests are close to shops, nightlife, restaurants, and beautiful Siesta Key Beach. Mainsail by Siesta Key Luxury Rental Properties is a rare blend of waterfront elegance, luxury amenities, and prime island location. From its private dock and expansive outdoor spaces to refined interiors and incredible waterway views, this home offers the perfect setting for a memorable Siesta Key escape. Book your stay at Mainsail today and experience the best of waterfront luxury on Siesta Key!

The Sarasota Starburst

Sarasota, FL, US
2 Bedrooms 6 Guests
Aug 24 - Sep 3
$205 night

Welcome to The Sarasota Starburst, a stylish mid-century sanctuary where 1960s Florida charm meets modern Florida luxury. Inspired by the iconic Sarasota School of Architecture movement, this home blends retro "pop" aesthetics with all the high-tech amenities a modern traveler needs. Whether you are here to lounge by the heated pool or need a bright, professional space for a "workation," this colorful retreat is your perfect Sarasota base. LOCATION HIGHLIGHTS - Central Sarasota: Nestled in a quiet neighborhood just minutes from the vibrant downtown scene. - Beach Proximity: A short drive to the world-famous white sands of Siesta Key and Lido Beach. - Neighborhood Vibe: Peaceful and residential, yet close to the best shopping and dining on the Gulf Coast. PROPERTY FEATURES - Heated Pool & Lanai: Enjoy year-round swimming in your private, screened-in oasis. - Pet-Friendly: A fully fenced-in backyard means your four-legged family members can vacation, too! - Work-from-Home Ready: A dedicated, professional workspace featuring a standing desk and dual monitors. - Retro Design: Authentic mid-century feel with "Sputnik" starburst wallpaper and curated pops of color. LIVING ROOM - Step into a sun-drenched, open-concept living area designed for relaxation. Large windows in the entry room flood the space with natural light, highlighting the clean lines and vintage-modern décor. - Whether you’re streaming your favorite shows on the Smart TV or curled up with a book, this room offers a bright and airy atmosphere for the whole group. - Sofa bed sleeps another 2 people KITCHEN AND DINING - The heart of the home is the "cozy-chic" kitchen, featuring sleek cabinetry and table seating for 4. - It is fully equipped with all the essentials for a home-cooked meal. Enjoy breakfast at the dining table, or head out to the covered patio to use the grill for a dinner by the pool. BEDROOMS AND BATHROOMS - Master Suite: Features a comfortable King bed, large closets, a Smart TV, and a private ensuite bathroom with a modern walk-in shower. - Second Bedroom: A beautifully decorated guest room with a Queen bed and plenty of natural light. - Bathrooms: Well-appointed with fresh linens and modern fixtures to ensure a spa-like stay. EXTRA PERKS - Beach Gear: We provide two beach chairs, a beach umbrella, and plush beach towels for your trips to the coast. - Laundry Room: Full-sized washer and dryer located in the laundry room for your convenience. - Parking: Attached garage suitable for a small vehicle, plus additional driveway parking. - Smart Tech: High-speed Wi-Fi and Smart TVs throughout - just bring your own streaming logins! NEARBY FAVORITES - The Ringling: Explore the historic circus tycoon’s estate and art museum. - St. Armands Circle: A premier destination for upscale outdoor shopping and gourmet dining. - Marie Selby Botanical Gardens: A world-class urban orchid garden on the bayfront. IMPORTANT INFO - Pet Policy: We are dog-friendly! Please let us know if you are bringing a pet. - Streaming Only: There is no cable TV; guests must use their own accounts for streaming services. - Pool Heat: The pool is heated for your comfort year-round (extra fee applies) - Quiet Hours: Please be mindful of our neighbors in this peaceful residential area. - There is a door camera for added security Experience the perfect blend of 1960s nostalgia and modern Sarasota living. From the "Starburst" kitchen to the sun-soaked lanai, every inch of this home is designed to help you relax, recharge, and enjoy the Florida sun. Book your stay at The Sarasota Starburst 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.

Paradise Palms!

Siesta Key, FL, US
3 Bedrooms 8 Guests
Aug 24 - 31
$378 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.

Golden Springs Estate

Siesta Key, FL, US
10 Bedrooms 28 Guests
Aug 24 - 27
$2,093 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 an exceptional dual-home retreat nestled on a private street just steps from the sugar-white sands of world-renowned Siesta Key Beach. This luxury estate is comprised of two beautifully appointed five-bedroom residences—Siesta Springs and Golden Set—each with its own private heated saltwater pool, rooftop deck, and Gulf-facing balconies—creating one expansive and cohesive coastal experience. Perfect for multi-generational families, group getaways, or multiple families traveling together, this combined estate offers nearly 7,200 square feet of indoor living space and can comfortably accommodate up to 28 guests in beds. Floor Plan Description (by level): Ground Level: Upon arrival, guests will find ample parking for up to eight vehicles, four covered spots and four additional driveway spaces. Each home boasts its own private, fenced backyard oasis designed for maximum relaxation and fun. Home A evokes Florida’s famous natural springs with a heated saltwater pool featuring a rock waterfall, integrated water slide, rock jump platform, and rope swing. Home B offers a sport-focused pool experience with a 20-by-30-foot volleyball court space built right into the pool. Both pools include generous sun shelves equipped with loungers, poolside basketball hoops, bubblers and pool lighting. Surrounding each pool, turf-lined mini-golf courses, outdoor connect 4 and bocce ball offer friendly competition, while the adjacent covered patios include smart TVs (3 in each home), ceiling fans, gas grills, and plentiful soft seating and dining areas for alfresco meals. A dedicated outdoor refrigerator and freezer at each property make poolside snacks and drinks easily accessible. For beach days, each home is stocked with two beach wagons, two coolers, ten beach chairs, and four adult bikes. Guests enter each home through spacious foyers with elevator and stair access to all upper levels, including the rooftop decks. The First Level of Living (2nd Floor): Each home’s second floor serves as its main indoor gathering space, featuring open-concept great rooms that combine the fully stocked kitchen, living area, and dining space. These expansive areas are ideal for entertaining, group meals, or simply enjoying family time, and they open onto furnished balconies for additional seating and fresh Gulf breezes. In Home A, the kitchen features a large pantry, full-size refrigerator with ice maker, freezer, double wall ovens, hooded cooktop, microwave, coffee maker, two dishwashers, toaster, crockpot, blender, and ample cookware, bakeware, cutlery, and serving pieces. The dining setup includes an 8-person dining table and 6-seat island bar. Home B mirrors these amenities with the addition of a 10-person dining table and seating for six at the island, offering combined seating for 30 guests. Each home includes a king bedroom on this level. Master Bedroom 2 in both homes features a king bed, en suite bathroom with a walk-in shower and double vanity with trough sink, and Juliet balconies accessible from both the bedroom and bath. A powder room is also available in each home on this floor for guest convenience. The Second Level of Living (3rd Floor): This floor includes three bedrooms per home—six total—each with private balconies and en suite baths, providing ultimate comfort and privacy for guests. In Home A, Bedrooms 3 and 4 each have king beds, balcony access, and en suite bathrooms featuring double vanities and walk-in showers. Bedroom 5 is a dream come true for children or teens with two custom full-over-full bunk beds, Nintendo Switch gaming console, two smart TVs, a lounge area, and an en suite bathroom with a shower/tub combo. Home B’s Bedrooms 3 and 4 also offer king beds, peeking Gulf views, private balconies, and en suite bathrooms with walk-in showers and double vanities. Bedroom 5 is thoughtfully curated for younger guests, boasting two full-over-full bunk beds, a rock-climbing wall, a cozy lounge, workspace with dual monitors for gaming or schoolwork, a smart TV, and an en suite bathroom with a combination shower and tub. Each home includes an oversized laundry room on this level with a utility sink and two stackable washer/dryer sets, making it easy to handle laundry for large groups. The Third Level of Living & Rooftop Deck (4th Floor): This top floor features each home’s primary master suite and an expansive club room—perfect for winding down or gathering for fun. Home A’s Master Bedroom 1 includes a king bed, private Gulf-facing balcony, walk-in closet, cozy reading nook, and a spa-like en suite bathroom with dual vanities, a freestanding soaking tub, walk-in double shower, and private water closet. The adjoining club room features a wet bar with beverage fridge, ice maker, and sink, and is outfitted with smart TVs, foosball table, Nintendo Switch gaming console, and games like wall Scrabble. A half bath and balcony leads to the staircase to the rooftop. Home B’s Master Bedroom 1 mirrors these luxurious features with Gulf views, balcony access, a freestanding tub, walk-in double shower, dual vanities, and private toilet room. The club room in this home is equally impressive with its own wet bar, beverage fridge, workstation, dual smart TVs and a shuffleboard. A half bath and stair access lead to the rooftop deck. Each rooftop deck rises 50 feet above ground, offering panoramic views of Siesta Key and the shimmering Gulf of Mexico. Outfitted with bar seating these spaces are perfect for morning coffee, mid-day sunbathing, or sunset cocktails. With unbeatable views and ambiance, they’re the highlight of your stay. https://www.youtube.com/watch?v=nc5JxIKjxqs https://www.youtube.com/watch?v=WNPfYYiwzlM Located just minutes from Siesta Key’s vibrant North and South Village districts, guests can explore shops, restaurants, bars, and grocery markets by walking, biking, or hopping aboard the free island 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 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! These Siesta Key luxury vacation rentals 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!

Tropical Retreat

Siesta Key, FL, US
4 Bedrooms 10 Guests
Aug 31 - Sep 2
$897 night

🌴 Tropical Retreat | Heated Pool + 1 Block to Siesta Key Beach 💖 Why You’ll Love This Home Two charming cottages, one unforgettable escape—Tropical Retreat brings together private indoor space and outdoor serenity just one block from Siesta Key Beach. With a screened-in heated pool, BBQ area, and alfresco dining, your group can unwind in complete exclusivity just steps from white sands and turquoise waters. 👨‍👩‍👧 Perfect For Ideal for multi-family vacations, couples traveling together, or groups wanting a flexible layout with separate spaces and shared outdoor amenities. 🎞️ Imagine This Wake up to the sounds of palm trees swaying and take your coffee to the poolside patio. The kids splash in the heated pool. Inside Coconut House, sunlight fills the open kitchen as you prepare lunch for the group. Meanwhile, a friend naps in the sunny bedroom upstairs at Palm Shade Cottage, enjoying the privacy of a separate retreat. Come evening, gather around the outdoor table for a tropical dinner under the stars as food sizzles on the grill. Take a sunset stroll to the beach—just one block away. 🛌 Where You’ll Sleep Coconut House • Bedroom 1: King Bed, Ensuite Bathroom, Ground Floor, TV • Bedroom 2: Queen Bed, Shared Hall Bath, Ground Floor, TV • Bedroom 3: Two Twin Beds, Shared Hall Bath, Ground Floor, TV Palm Shade Cottage • Bedroom 4: Queen Bed, Ensuite Bath, Second Floor, TV • Common Space: Full Murphy Bed, Hall Bath, Ground Floor 📍 Explore the Area • 0.1 miles to Siesta Key Beach – White sand, turquoise water, beach access • 0.4 miles to Siesta Key Village – Boutique shops, island eateries, and nightlife • 0.2 miles to Siesta Public Beach Park – Kayak rentals, picnic tables, and family-friendly park space • 0.3 miles to Local Cafés and Bakeries – Fresh coffee, pastries, and ocean views • 0.5 miles to Turtle Beach Trail – Scenic walking path and coastal wildlife • Coastal energy meets quiet, residential surroundings for a relaxing stroll ⌛ 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 are provided for a seamless first couple of nights. Free high-speed WiFi is included. This pool is heated between November 15–April 15. This is a combined duplex property—Coconut House (606B) and Palm Shade Cottage (606A) are accessed by separate entrances and do not share interior space. Coconut House is a single-floor unit. If any guest has difficulty with stairs at Palm Shade Cottage, please contact us for alternative accommodations.

La Contento Casa - 5560

Siesta Key, FL, US
3 Bedrooms 8 Guests
Aug 24 - 31
$637 night

"🌴 La Contento Casa | Private Heated Pool, Walk to Siesta Key Village and Beach 💖 Why You’ll Love This Home Awaken to sun-drenched mornings and tranquil canal views in this inviting waterfront retreat. La Contento Casa offers a seamless blend of indoor comfort and outdoor serenity, promising an escape where every moment feels like a breath of fresh air. 👨‍👩‍👧 Perfect For Families seeking a memorable beach vacation, couples desiring a peaceful waterfront escape, or small groups looking for a comfortable and convenient base to explore Siesta Key. 🎞️ Imagine This Your day begins with a gentle breeze drifting in as you relax on your covered back porch, watching the palms sway. After a leisurely breakfast prepared in the gourmet-grade kitchen with its convenient window pass-through to the patio, you gather your beach essentials—provided for your convenience—and take the short, invigorating 10-minute walk to Siesta Key Beach, feeling the world-famous white sands beneath your toes. Back at La Contento Casa, the private heated pool is waiting, followed by an afternoon lounging by the water, perhaps with a drink crafted at your outdoor bar with sink. As evening approaches, the scent of a home-cooked meal fills the air, enjoyed alfresco with the canal views as your backdrop. Later, unwind in the spacious living area, sharing stories and laughter, before drifting off to sleep in one of the comfortable king beds, dreaming of another perfect day in paradise. 🛌 Where You’ll Sleep - Bedroom 1: King Bed, shared bath, main floor, TV - Bedroom 2: King Bed, shared bath, main floor, TV - Bedroom 3: Two Twin Beds, shared bath, main floor, TV - Bonus Room: Two Rollaway Beds, located in common area 📍 Explore the Area Discover the best of Siesta Key with ease. 0.4 miles to Siesta Key Beach, renowned for its crystal-white quartz sand. Enjoy a delightful stroll or quick drive to Siesta Key Village (1.4 miles), offering an array of charming boutiques, diverse dining options, and vibrant coastal energy. 📝 Your Siesta Key Escape Awaits 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. This pool is heated between November 15 - April 15. Please note: There is 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."

Waters Edge - 5049

Siesta Key, FL, US
3 Bedrooms 8 Guests
Aug 26 - Sep 2
$636 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."

Silver Shore - 657B

Siesta Key, FL, US
3 Bedrooms 12 Guests
Aug 30 - Sep 1
$967 night

🌴 Silver Shore | Modern Escape, Rooftop Deck, Pool & Across from Siesta Key Beach 💖 Why You’ll Love This Home From morning coffee on the rooftop to sunset dips in your private heated pool, Silver Shore invites you to unwind in total comfort. Spacious enough for large families or groups, this upscale retreat offers elevator access, beach proximity, and modern style—all in one beautifully designed unit which is apart of a shared duplex. 👨‍👩‍👧 Perfect For Perfect for multigenerational families or groups seeking luxury, space, and easy access to Siesta Key Beach and Village—all with bonus rooftop views! 🎞️ Imagine This The open-concept layout welcomes you with designer furnishings, sleek finishes, and a kitchen that’s made for group feasts and late-night snacks. As the kids scatter to the bunk room and adults claim their king suites, the home hums with anticipation. Outdoors, your private backyard and heated pool offer space to lounge, splash, or grill. When the day slows, head to the shared rooftop lookout—wine in hand—to soak in panoramic island views as dusk paints the Gulf in coral tones. Then retreat to your serene bedrooms, where high-end beds and blackout shades promise deep, restful sleep before another beach-filled day. 🛌 Where You’ll Sleep - Bedroom 1: King Bed, Ensuite Bath, Upper Floor, TV - Bedroom 2: King Bed, Shared Bath, Upper Floor, TV - Bedroom 3: Two Full Over Full Bunk Beds, Shared Bath, Upper Floor, TV 📍 Explore the Area - 0.1 miles to Siesta Key Public Beach Access - 0.6 miles to Siesta Key Village – shops, fresh seafood, nightlife & boutiques - Walkable, bike-friendly neighborhood with island energy - Kayak, bike, or paddle board rentals available nearby 📝 Your Siesta Key Escape Awaits Silver Shore blends modern comfort with unbeatable beach access—plus a rooftop deck that’s hard to top. Book now and arrive knowing your home has been meticulously cleaned under our CottageClean™ program, including a 6-hour deep clean and 35-point inspection before each guest’s arrival. 📝 Need to Know: This unit is one side of a duplex. Guests will have private access to the right-side garage, a private backyard and pool area, the entire fourth floor, and the right side of the third floor. The third floor is divided by a wall, providing a fully private space on your side. A shared exterior spiral staircase leads to the shared rooftop deck, which may be accessed by guests of the neighboring unit. Please contact us if you have any questions about the layout of this duplex. Starter Supplies: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. Free High-Speed WiFi. Heated Pool: Heated from November 15 – April 15. This home has stairs and an elevator. Please contact us if any guest has mobility concerns. • Related Units: Looking for more space or options? Book other units in the same building:  • 6 Bedroom Option: Beach Dream  • 3 Bedroom Option: Crystal Sands

Beach Dream

Siesta Key, FL, US
6 Bedrooms 22 Guests
Aug 30 - Sep 1
$1,976 night

🩴 Beach Dream | 6BR with Rooftop Patio, Two Private Heated Pools, and a 2-Min Walk to Siesta Key Beach 💖 Why You’ll Love This Home Welcome to Beach Dream, a luxurious 6-bedroom entire duplex offering dual private pools, a rooftop lookout, and a prime location to Siesta Key Beach just across the street. With modern interiors, sleeping for up to 22 guests, it’s the perfect space for reunions, retreats, and unforgettable coastal gatherings. 👨‍👩‍👧 Perfect For Ideal for large families, multi-generational groups, wedding parties, or friends traveling together—Beach Dream gives you the privacy of two units with the shared benefits of rooftop sunsets and unbeatable walkability to the beach and village. 🎞️ Imagine This Wake up just steps from the sand, where two fully private heated pools await your crew’s morning splash. Each part of this stylish duplex boasts its own modern living space, full kitchen, and designer bedrooms, giving your group the ability to gather together while also spreading out when needed. Prepare meals in either sleek kitchen, or host a group dinner al fresco on the patios. Spend afternoons lounging in one of the two fenced backyards or sipping cocktails on the shared rooftop lookout, with panoramic views of Siesta Key’s shimmering Gulf waters. With dual laundry rooms and TVs in every bedroom, Beach Dream is both functional and fabulous for group living. As night falls, retreat to one of six beautifully appointed bedrooms, including four with king beds and two expansive bunk rooms that sleep up to 14 combined. Whether you’re planning lazy beach days or lively evenings in Siesta Key Village, Beach Dream is the elevated group escape you’ve been dreaming of. 🛌 Where You’ll Sleep Crystal Sands: • Bedroom 1: King Bed, Ensuite Bath, 2nd Floor, TV • Bedroom 2: King Bed, Shared Bath, 2nd Floor, TV • Bedroom 3: Full Over Full Bunk Bed & Full Bed, Shared Bath, 2nd Floor, TV Silver Shore • Bedroom 4: King Bed, Ensuite Bath, 4th Floor, TV • Bedroom 5: King Bed, Shared Bath, 4th Floor, TV • Bedroom 6: Two Full Over Full Bunk Beds, Shared Bath, 4th Floor, TV 📍 Explore the Area • 0.1 miles to Siesta Key Public Beach Access • 0.6 miles to Siesta Key Village – a short walk to dining, boutiques, and nightlife • Rent kayaks, paddle boards, and bikes nearby • Enjoy local cafés, sunset bars, and family activities all within easy reach 📝 Your Siesta Key Escape Awaits A rare find for large groups, Beach Dream offers two duplex homes, two pools, and a rooftop deck just a 2-minute walk to the beach. Your stay includes our trusted CottageClean™ program—a deep, 6-hour clean and 35-point inspection before every guest. Now is the time to book your dream group getaway! Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. Free High-Speed WiFi. Both pools are heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. Stairs: Both units have stairs. Contact us if any guest has mobility concerns. Duplex Note: This listing includes both duplex units. Guests will have access to the entire unit, including both private pools and backyards. Related Units: Prefer to book just one part of the duplex? View individual listings:  • 3 Bedroom Option: Crystal Sands  • 3 Bedroom Option: Silver Shore

Villa Champagne - 5322

Siesta Key, FL, US
4 Bedrooms 8 Guests
Aug 25 - 27
$978 night

🌴 Villa Champagne | Private Pool, Walk to Siesta Key Beach and Island Living 💖 Why You’ll Love This Home Wake up to canal views, sip coffee on a sunlit balcony, and unwind in your private pool and spa after beach-filled days. Close to Siesta Key Beach and Siesta Key Village, Villa Champagne offers coastal luxury just steps from everything you love about the island. 👨‍👩‍👧 Perfect For Families, couples, or friend groups looking for a spacious coastal home with all bedrooms upstairs, outdoor living spaces, and sunset views. 🎞️ Imagine This Start your morning with a stroll to a nearby café in the Village before heading to the powder-soft sands of Siesta Key Beach. Back at the house, prep lunch or fire up the BBQ for grilled dinner. Soak in the spa as the sun sets over the canal, then toast the evening from your private balcony or comfy outdoor lounge. Every moment here invites you to slow down and savor island life. 🛌 Where You’ll Sleep • Bedroom 1: King Bed, Ensuite Bathroom, Walk-In Shower & Soaking Tub, Private Balcony, TV • Bedroom 2: Queen Bed, Hall Full Bath, TV • Bedroom 3: Queen Bed, Shared Full Bath, TV • Bedroom 4: Two Twin Beds, Shared Full Bath, TV 📍 Explore the Area • 0.4 Miles to Siesta Key Beach Access 10 – Soft White Sand & Turquoise Waters • 0.9 Miles to Siesta Key Village – Shops, Dining, Music & More • 0.7 Miles to Siesta Key Beach Pavilion • Just Minutes to Downtown Sarasota, and Local Art Galleries on the Free Trolly ⌛ Don’t Wait - This island getaway books quickly. Your stay includes our CottageClean™ promise: a 6-hour deep clean followed by a 35-point inspection—so you arrive at a spotless home. 📝 Need to Know: Starter packs of kitchen and toiletry essentials are provided for the first couple of nights. Free high-speed WiFi is available throughout the home. Exterior security cameras are installed at the front-door entry and at the back of the home facing the landscaping for security purposes only. No cameras are located inside the home or directed toward private guest areas.

Nicely Updated, Large Home Just Minutes to Siesta Key and Downtown Sarasota, 2 Game Rooms

Sarasota, FL, US
4 Bedrooms 10 Guests
Aug 24 - 31
$446 night

Welcome to our stunning pool home in Sarasota, Florida! This large and spacious 4-bedroom, 2-bath, dog-friendly retreat is perfectly located just 10 minutes away from the world-renowned Siesta Key beaches and the vibrant downtown Sarasota. With its beautiful updates and modern furnishings, this home offers a delightful blend of comfort and style for your vacation. Highlights and Amenities • Spacious open floor plan perfect for Family & Friend Gatherings • Heated swimming pool with pool-side loungers • Pet-friendly with private fenced-in backyard oasis • Outdoor seating areas, and BBQ grill • Fully stocked beach essentials, including beach chairs, cooler, and umbrella • Lightweight Sand Resistant Turkish Beach Towels Provided • High-Quality Linens and Plush Bath Towels • High Speed Internet and Wi-Fi, Smart TVs for Streaming • Close to Downtown Sarasota restaurants, shops, galleries, and nightlife • Short drive to Siesta Key, Lido Key, and Sarasota’s top rated beaches • Pool Table and Ping Pong Tables • Free Trolley for convenient transportation • Near top-rated parks and golf courses As you step inside, you’ll immediately notice the attention to detail and the welcoming ambiance. The house is tastefully decorated throughout, exuding a modern flair that creates an inviting atmosphere for all guests. With its ample space and thoughtful layout, this vacation home comfortably accommodates up to 10 guests, making it an ideal choice for families or groups of friends. The bedrooms in this home are designed with your comfort in mind. There are two bedrooms with king beds, one bedroom with a queen bed, and a fourth bedroom featuring a bunk bed with a trundle. Additionally, there is a queen pullout sofa available for extra sleeping arrangements. Each bedroom is tastefully furnished, providing a cozy and relaxing retreat after a day of exploring the Sarasota area. One of the highlights of this vacation home is the theatre game room, complete with a generously sized 75" SMART TV, gaming console and pullout couch. Whether you’re in the mood for a movie night or some friendly competition, this room offers the perfect space to unwind and have fun. In the oversized two-car garage, you’ll find a pool table and ping pong table, adding to the entertainment options available for you and your guests. The open living area seamlessly combines a spacious living room, a cozy fireplace with comfortable chairs, a formal dining room, and a gourmet kitchen. The kitchen is a chef’s dream, featuring granite countertops, wood cabinetry, and top-of-the-line stainless steel appliances. With a kitchen counter boasting four barstools and an additional eat-in area with bench seating for five, there’s plenty of room for everyone to gather and enjoy meals together. The backyard of this vacation home is a true oasis. Step outside to discover a crystal clear pool, sun loungers, and an outdoor table and chairs, perfect for al fresco dining or simply soaking up the Florida sunshine. A gas grill is provided for those who enjoy cooking outdoors, and an outdoor fireplace adds a touch of warmth and ambiance to your evenings. Surrounding the pool area is a lovely garden, creating a serene and peaceful atmosphere. Whether you’re looking to relax by the private pool, explore the famous beaches, or immerse yourself in the vibrant culture of downtown Sarasota, this vacation home offers the perfect base for your Florida getaway. With its convenient location, modern amenities, and spacious design, you’re sure to create unforgettable memories during your stay in this beautiful Sarasota retreat. Other Things to Note: ---------------------------------------- Pet Fee: This is a pet friendly home. Please include your pet in your booking so we can make the appropriate arrangements for the departure cleaning. A $125 pet fee, per pet is required to help remove pet hair and dander from any furnishings and floors for our future guests. Thank you for your understanding, and we look forward to hosting you and your pup! Pool Heater: We recommend only heating the pool in the months of October through May, as the pool during summer months should not need heating. If you’d like the pool heated during your stay, please let us know at least 24–48 hours before your arrival so we can have it ready for you. A $12 daily heating fee applies to help cover energy costs. Please note, if you request heating after check-in, a $50 service fee will be added for our team to come out and activate the heater. Dogs are not allowed in the pool at any time as the filtration system is not designed for filtering pet hair. Thank you for your understanding—we want to ensure you enjoy a comfortable and relaxing swim! ---------------------------------------- City of Sarasota VR24-00154

Siesta Springs

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. 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!

4 Mi to Siesta Key Beach! Spacious Family Getaway

Gulf Gate Estates, FL, US
3 Bedrooms 8 Guests
Aug 26 - 28
$175 night

Pet Friendly w/ Fee | 3 Bikes | Wheelchair Accessible | 4 Mi to Village Green Golf Club | 6 Mi to Dtwn Sarasota Sunshine State bliss begins upon arrival at this vibrant Sarasota vacation rental! Dive straight into your own private oasis, where a large lanai frames a sparkling pool and spa, and roomy indoor spaces seamlessly meet a kitchen designed to feed your crew. After sunny beach days, head home to fire up the gas grill for a family BBQ. Your next Gulf Coast getaway is just a click away! -- THE PROPERTY -- OUTDOOR LIVING - Lanai, private pool (heated w/ fee), hot tub - Furnished patio, gas grill - 3 adult-sized bicycles INDOOR LIVING - Smart TVs, board games - Dining table - Washer, dryer - Central A/C & heating KITCHEN - Electric stove, oven, dishwasher - Keurig coffee maker - Toaster, microwave, air fryer - Cooking basics, dishware & flatware ACCESSIBILITY - Single-story home - Step-free access via garage - Wheelchair accessible PARKING - Garage (2 vehicles) - Driveway (2 vehicles) - Trailer parking -- THE LOCATION -- - A paradise for sun-seekers, just minutes from the world-renowned white quartz sands - Walk to Detwiler's Farm Market for fresh local groceries & delicious bakery treats - Close to Gulf Gate dining, shopping & local entertainment options - 6 miles to Marie Selby Botanical Gardens' stunning bayfront displays & tropical air plants - 10 miles to Lido Key Beach - 11 miles to The Ringling Museum Complex, Ca' d'Zan mansion, & iconic circus history exhibits -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $50 fee (+ fees & taxes, 1 max) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - Quiet hours (after 11:00 PM) ADDITIONAL INFORMATION - Optional $25 nightly pool heat fee (+ fees & taxes, paid pre-trip, applied to entire stay)

Sunset Lagoon Estate

Siesta Key, FL, US
10 Bedrooms 28 Guests
Aug 27 - 30
$2,093 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 an extraordinary dual-home retreat on a private street just steps from the award-winning sands of Siesta Key Beach. Combining two luxurious five-bedroom homes – Blue Lagoon and Serving Sunset into one expansive estate, this vacation destination is ideal for extended families or multi-family groups seeking style, space, and the serenity of the Gulf Coast. This nearly 7,200-square-foot estate offers ten total bedrooms, ten full bathrooms, and four half baths—comfortably accommodating up to 28 guests in beds. Both homes include private heated saltwater pools, rooftop decks 50 feet above ground with Gulf views, club rooms, and balconies on all levels. The property is fully fenced, pet-friendly (fees and restrictions apply), and built for entertainment and relaxation at every level. Floor Plan Description (by level): Ground Level: On arrival, guests are greeted by parking for up to eight vehicles—four covered and four in the driveways. Each home features its own fully fenced backyard oasis. Unit A’s pool is styled after a natural Florida spring, complete with a cascading rock waterfall, an integrated waterslide, a rope swing, poolside basketball hoop and a rock jump platform. Meanwhile, Unit B features a volleyball-themed pool with a 20x30-foot court area and adjacent lounging zones for spectators. Both pools include expansive sun shelves, bubblers, and LED lighting. Behind the pools, each yard offers a custom turf mini-golf course. The adjacent covered patios are ideal for outdoor living and feature smart TVs (Home A has 2 and Home B has 3), natural gas grills, ceiling fans, outdoor connect 4 and bocce ball games and abundant soft seating and dining spaces. Each home provides a refrigerator and freezer near the patio for poolside snacks and drinks, and the beach gear setup includes two wagons, two coolers, ten beach chairs, and four adult bikes per home. These resort-style grounds are private, secure, and perfect for both adults and kids to relax and play freely. Guests also enter each home through a welcoming foyer with elevator and stair access to all upper levels, including the club rooms and rooftop decks. The First Level of Living (2nd Floor): This level functions as the primary shared space in both homes and includes the kitchen, dining, and living areas. Each great room is designed with comfort and flow in mind, connecting easily to balconies with additional outdoor seating. In Home A, the fully stocked chef’s kitchen includes a large pantry, cooktop with hood vent, dual wall ovens, full-size refrigerator with ice maker, freezer, two dishwashers, microwave, coffee maker, toaster, blender, crockpot, and extensive cookware and serve ware. Guests can dine together at the 8-person dining table or the 6-seat kitchen island. The adjacent living area offers plush seating, a large smart TV, and balcony access for enjoying the Gulf breeze. Home B mirrors these high-end finishes and appliances. The dining area seats 13 total guests with space for eight at the table and five at the island. Both homes’ open-concept layouts ensure everyone remains connected—whether preparing meals, watching a movie, or enjoying happy hour outdoors. Each home also includes a king-bedroom on this level. Master Bedroom 2 in both homes features a king bed, dual Juliet balconies (one from the bedroom, one from the en suite bath), and a luxurious en suite bathroom with a walk-in shower and double faucet vanity with trough sink. A convenient half bath is also located in each home on this level. The Second Level of Living (3rd Floor): This level houses three bedrooms in each home, for a total of six guest suites. All bedrooms feature balcony access and en suite bathrooms, providing privacy and comfort for everyone in your group. In Home A, Bedrooms 3 and 4 each include a king bed, balcony access, and en suite bathrooms with walk-in showers and double vanities. Bedroom 5 is a custom bunk room designed with kids in mind—it features two full-over-full bunk beds, two smart TVs and dual monitors perfect for gaming or productivity. This suite also includes a city closet and en suite bath with a shower/tub combo. In Home B, Bedrooms 3 and 4 echo the same upscale design, each with a king bed, en suite bath, and private balconies with peeking Gulf views. Bedroom 5 is another children’s favorite with two full-over-full bunk beds, a rock-climbing wall, a smart TV, and a fun layout designed to entertain. Its en suite bath includes a combination tub and shower. Each home also features an oversized laundry room with a utility sink and dual stackable washer/dryer sets on this floor, making mid-stay laundry a breeze. The Third Level of Living & Rooftop Deck (4th Floor): The top floor in each home blends luxurious sleeping quarters with elevated entertainment spaces. Each home’s Master Bedroom 1 is a sanctuary of comfort and style. In Home A, the suite includes a king bed, Gulf views, walk-in closet, balcony access, and a stunning en suite bathroom with dual vanities, a freestanding soaking tub, walk-in double shower, and a private water closet. Home B’s Master Bedroom 1 is similarly appointed, offering direct rooftop access, a king bed, Gulf-facing balcony, and a spa-like en suite with walk-in double shower, dual vanities, freestanding tub, and a private water closet. The club rooms on this level are made for entertainment and relaxation. In Home A, the club room features a wet bar with sink, beverage and wine fridges, and an ice maker. Entertainment options include a smart TV, Nintendo Switch gaming consoles, wall Scrabble, and air hockey. A half bath and balcony provide access to the rooftop deck. In Home B, the club room includes shuffleboard, dual smart TVs, and a workstation—along with a wet bar and beverage fridge. A half bath and stairway lead directly to the rooftop deck. These rooftop spaces are ideal for coffee at sunrise or cocktails at sunset, with panoramic views stretching across Siesta Key and the Gulf of Mexico. Outfitted with comfortable seating, these elevated retreats are unforgettable highlights of the estate. https://www.youtube.com/watch?v=VrmBWqJtdvo https://www.youtube.com/watch?v=eHzunY8jO74 Steps to Your Private Beach! Guests can walk, bike, or ride the free island trolley to explore Siesta Key’s North and South Village entertainment districts filled with restaurants, bars, shops, and groceries. Downtown Sarasota is a quick 10–15-minute drive for world-class dining, theater, and waterfront parks, and day trips to Lido Key, Anna Maria Island, or even Orlando’s major attractions are easy and accessible. These Siesta Key luxury vacation rentals feature 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 both homes being equipped with private elevators providing access to all interior levels (excluding the rooftop deck), 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!

Vacation Rentals in South Sarasota by Amenities & Features

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Vacation Rentals Near South Sarasota

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