Vacation rentals in Sarasota, FL with a pool

3 Bedrooms • 8 Guests

$206 night

Experience the perfect Sarasota getaway! This beautifully updated 3-bedroom, 2-bath vacation home combines comfort, convenience, and a prime location just steps from Ed Smith Stadium, home of the Baltimore Orioles Spring Training. Whether you’re planning a family vacation, beach escape, golf trip, or baseball getaway, you’ll love being just minutes from Sarasota’s best attractions. Spend your days lounging by your private screened pool (pool heat available as an add on amenity at $35 plus tax per day and should be arranged at least 3 days prior to check in to allow for scheduling), exploring the vibrant shops and restaurants of Downtown Sarasota, or soaking up the sun on the white sands of Lido Key Beach, located less than 5 miles away. World-famous Siesta Key Beach, St. Armands Circle, and Sarasota’s arts and cultural attractions are all within an easy drive. Inside, the bright, open-concept living space is designed for relaxing after a day of adventure. The comfortable living room features soaring ceilings, plenty of natural light, and a large smart TV for movie nights. The fully equipped kitchen opens to the living area, making it easy to prepare meals while staying connected with family and friends. A spacious dining area provides plenty of seating for everyone. Things To Note- Pet Policy- One well-behaved dog considered with PRIOR approval and $200 pet fee + tax, No cats. Pool Heater- Is available as an add on amenity at $35 plus tax per day and should be arranged at least 3 days prior to check in to allow for scheduling. Stays of greater than 30 nights may require a mid-stay clean and would be arranged through management. VR-24-00135 What Guests Love- Private screened swimming pool Walk to Ed Smith Stadium Less than 5 miles to Lido Key Beach Minutes to Downtown Sarasota, St. Armands Circle & Siesta Key Fully equipped kitchen Smart TVs & high-speed Wi-Fi Driveway parking Bright, open floor plan with vaulted ceilings Quiet residential neighborhood Sleeping Arrangements Primary Bedroom: King Bed with ensuite bath Guest Bedroom: Queen Bed Guest Bedroom: Two Twin Beds (or customize to your actual setup) The Perfect Sarasota Location You’ll be in the heart of everything Sarasota has to offer- Ed Smith Stadium: Walkable- 3–5-minute walk Downtown Sarasota: Approximately 2 miles Lido Key Beach: Less than 5 miles St. Armands Circle: Less than 5 miles Siesta Key Beach: Approximately 7 miles Restaurants, shopping, golf courses, parks, and marinas all nearby. Whether you’re attending Spring Training, enjoying a beach vacation, or exploring Sarasota’s award-winning dining and arts scene, this home offers the ideal home base for your Florida escape. Book your Sarasota vacation today and enjoy the perfect combination of location, comfort, and your own private pool! License: VR-24-00135

Vitamin Sea

4 Bedrooms • 8 Guests

$182 night

What Guests Love- Private Pool – Optional heat (Nov–Apr) for $35/day + tax; must be scheduled before arrival Screened Lanai – Outdoor seating, ambient lighting, and poolside lounging Propane Grill – Perfect for outdoor cooking Beach Gear – 2 chairs, umbrella, cooler Garage & Parking – One-car garage with automatic opener + driveway parking Fully Stocked Kitchen – Modern appliances, granite countertops, bar seating, plus separate dining area for 6 Spacious Living Room – 2 large sofas, flat-screen TV, and lanai access 1 set of towels (1 bath, 1 hand, and 1 washcloth) are provided per person for the max number of people the home sleeps Laundry Room – Full-size washer/dryer Guest House – Private kitchenette, bathroom, and living area Tech & Comfort – Wi-Fi, Streaming TV, central A/C Pet Friendly – One small, well-behaved dog considered ($200 pet fee + tax, approval required). No cats. No Smoking inside the home Location Highlights 8 minutes → Gillespie Park (dog park, pickleball, tennis, trails, fitness equipment) 6 minutes → Payne Park (dog park, skate park, disc golf, playgrounds, cafe) 5 miles → Lido Beach 7 miles → Siesta Key Beach 20 minutes → Sarasota/Bradenton Airport Close to downtown Sarasota for dining, shopping, and nightlife Welcome to your private Sarasota retreat, featuring a sparkling pool (heat optional), screened lanai, and a detached guest house for ultimate comfort and privacy. The main house offers an open-concept floor plan with a modern kitchen, dining space, and two spacious living rooms with that opens to the lanai. Three bedrooms include a master suite with en-suite bath and two guest rooms with convenient access to a shared bathroom. The guest house by the pool is a perfect setup for extended family, friends, teens, or a nanny. It features a king bed, TV, sofa, kitchenette, washer/dryer, full bath, and a cozy private patio. Whether you’re unwinding by the pool, grilling outdoors, or heading out to enjoy Sarasota’s white-sand beaches, lively downtown, or family-friendly parks, this home is the perfect place to make lasting memories! 4 BR / 3 BA / Sleeps 8 Sarasota FL 34237 Vacation Rental License # 25-VR-000004 Minimum stay duration of 7 days/nights Sleeping Arrangements Master Bedroom – Queen bed with en-suite bathroom Guest Bedroom 1 – Queen bed with en-suite bathroom Guest Bedroom 2 – King bed, shares hallway bath with tub/shower combo Guest Bedroom 3 (Detached Guest House, 320 sq ft) – King bed, King sofa, TV, beverage fridge, table with 2 chairs, washer/dryer, full bathroom, and small private patio/courtyard by the pool Note: Main house also offers a Full-size Sofa Bed Professionally cleaned and sanitized per CDC guidelines between each stay. Extended stays (60+ days) require a mid-stay professional clean (fee applies). License: 425-VR-000004

Casamigos - 1805

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.

2440 Floyd St

6 Bedrooms • 10 Guests

$1,051 night

Welcome to 2440 Floyd Street, a stunning, modern retreat in the heart of Sarasota. This spacious 6-bedroom, 4.5-bathroom home offers luxury, comfort, and privacy, making it the perfect getaway for families, groups, and corporate travelers. With a heated pool, private rooftop terrace, and a detached guest house, this home offers a true resort-style experience just minutes from Siesta Key Beach, Lido Key, and downtown Sarasota. The Space Designed for both relaxation and entertainment, this home features an open floor plan, soaring ceilings, and beautiful wood floors throughout. The gourmet kitchen boasts a large marble island, high-end Fulgor appliances, and ample pantry space, perfect for cooking up a feast or enjoying a casual breakfast. The living area is a stylish, welcoming space with plush seating, contemporary decor, and large sliding doors that open up to the outdoor patio and pool area, seamlessly blending indoor and outdoor living. Whether you’re here for a family vacation, corporate retreat, or special getaway, this Sarasota home provides the perfect blend of luxury, comfort, and prime location. Bedrooms & Bathrooms • Primary Suite (Main Floor) – King bed, spa-like ensuite bathroom with soaking tub, dual sinks, and walk-in shower with elegant marble accents. Direct pool access. • Downstairs Guest - 1 Queen Bed • Upstairs Bedroom 1 – Queen bed, ensuite bathroom • Upstairs Bedroom 2 – Queen bed, private balcony with cozy outdoor seating • Upstairs Bedroom 3 – Two twin beds, bright and airy • Detached Guest House – Queen bed, kitchenette, dining for 4, ensuite full bathroom All bedrooms are designed with luxurious linens, designer furnishings, and ample closet space to ensure a comfortable and restful stay. Outdoor Paradise ✔ Heated pool with lounge seating ✔ Outdoor kitchen with grill ✔ Covered patio off the living room with dining and lounge space ✔ Rooftop terrace with plush seating, perfect for sunset cocktails ✔ Tropical landscaping with Oak trees for shade Additional Amenities ✔ 2-Car Garage & Ample Driveway Parking ✔ Laundry Room with Washer & Dryer ✔ Smart TVs, High-Speed WiFi, and Work-Friendly Spaces ✔ Beach Gear for the Whole Group – chairs, umbrellas, coolers, and kids’ toys Prime Location – Close to Everything! Located in Sarasota’s charming and historic Arlington Park neighborhood, this home offers a peaceful, walkable setting while being just minutes from top attractions: ✔ Downtown Sarasota – Vibrant nightlife, fine dining, and boutique shopping (5-minute drive) ✔ Siesta Key Beach – Ranked among the best beaches in the world (10-minute drive) ✔ Lido Key & St. Armands Circle – Upscale shopping and dining (15-minute drive) ✔ Pinecraft (Mennonite & Amish Community) – Local markets and homemade treats Additional Properties: This property is adjacent to 2 additional 6-bedroom properties and 1 additional 5 bedroom property adding additional sleeping space for 34 additional guests. We welcome large groups who are looking to house several people across multiple properties. Please inquire for more information. What’s provided for your stay: Have fun at the beach with chairs, coolers, umbrellas, toys and more, pre-stocked into the villa prior to your arrival. Each residence has their own Property Liaison to ensure any problems or concerns will be resolved in an effective and timely manner. **Minimum Age 25: All Reservations must be booked by and accompanied by an adult who is 25 years of age or older. Valid photo I.D. may be required at the time of booking. **Property is monitored by video and audio surveliance on the exterior of the property. This property is located in a quiet residential neighborhood. Parties will not be tolerated. Standard Occupancy for this property is 6 guests. Each guest above 6 will be charged an additional $50/night. Pet Fee: 2 Dogs of up-to 50lbs are welcome at our property. An additional pet fee of $35/night/pet will be applied.

The Patterson

3 Bedrooms • 5 Guests

Aug 26 - Sep 2

$376 night

Cert # VR25-00083 Peaceful Coastal Retreat with Pool — Steps from Sarasota Bay Welcome to your serene escape in the heart of Sarasota’s vibrant Indian Beach Sapphire Shores neighborhood. Just one block from the shimmering Sarasota Bay and minutes to downtown nightlife, this charming 3-bedroom, 2-bath home offers the perfect blend of relaxation and accessibility. Property Highlights: 3 bedrooms, 2 bathrooms – Sleeps 5 comfortably Private screened-in pool with loungers, outdoor dining for 6, TV, and propane grill Chic, coastal-inspired decor with designer touches throughout Fully equipped kitchen, modern appliances, and indoor/outdoor dining areas All bedrooms feature TVs for personalized relaxation Dedicated home office with desk, smart TV, and sleeper sofa – perfect for remote work Master suite with queen bed and ensuite bathroom Tropical landscaping and tranquil outdoor spaces for morning coffee or evening cocktails Step inside to find a beautifully curated interior designed with comfort and calm in mind—decorated with tropical accents, curated artwork, and warm, welcoming tones. The spacious primary suite features a queen bed, ensuite bathroom, and smart TV. A second queen bedroom offers comfort and privacy, while the third bedroom doubles as a home office, complete with a pull-out sofa, smart TV, and dedicated workspace—ideal for remote workers or extra guests. Gather in the inviting living room, cozy up by the candle lit fireplace, or enjoy meals in the sunlit dining area under a statement chandelier. Each room is outfitted with thoughtful design details, TVs, and ceiling fans for comfort and entertainment. Outside, your private screened-in pool awaits—surrounded by lush tropical landscaping for the ultimate in privacy and serenity. Lounge poolside, dine al fresco under the stars at the outdoor dining table for six, enjoy the outdoor TV, and fire up the propane grill for family barbecues. Neighborhood & Location: Located in the historic Indian Beach Sapphire Shores district—home to stately banyan trees, charming architecture, and a laid-back coastal vibe—this home places you in the heart of Sarasota’s arts and cultural corridor. Just blocks from: 1 block to Sarasota Bay for morning walks and sunset views A short stroll to the Ringling Museum of Art & Ringling College of Art + Design Close to New College of Florida and FSU Sarasota-Manatee Only 2 miles to Downtown Sarasota, known for its lively arts scene, gourmet restaurants, live music, weekend markets, and stylish bars 3.5 miles to Lido Key Beach & St. Armands Circle — perfect for boutique shopping and beachfront dining 10 miles to world-famous Siesta Key Beach, consistently ranked among the top beaches in the U.S. Whether you’re here for the beach, arts, or a quiet work-from-paradise getaway, this thoughtfully equipped home provides the perfect base for your Sarasota escape. Amenities Fast Wi-Fi Smart TVs in every room Washer/dryer in unit Central A/C Beach Chairs, Cooler, Umbrella provided Beach towels Parking in driveway Perfect For: Families Couples’ getaways Remote workers Ringling College visitors Snowbirds Why You’ll Love It Here: This peaceful getaway combines resort-style outdoor living with the comfort of a thoughtfully curated interior. Whether you’re enjoying a dip in the pool, grilling under the palms, or heading out for a day at the beach, you’ll have everything you need to relax, recharge, and explore Sarasota’s vibrant lifestyle. Pet Policy The Patterson is Dog-Friendly for 1 Dog of 50lbs or fewer . An additional $35/night/dog pet fee will be applied for guests with pets. Guests with Pets must sign the Pet Waiver. Property Notes **Minimum Age 25: All Reservations must be booked by and accompanied by an adult who is 25 years of age or older. Valid photo I.D. may be required at the time of booking. **Property is monitored by video and audio surveillance on the exterior of the property. This property is located in a quiet residential neighborhood. Parties will not be tolerated. What’s provided for your stay: Have fun at the beach with chairs, coolers, umbrellas, toys and more, pre-stocked into the villa prior to your arrival. Each residence has their own Property Liaison to ensure any problems or concerns will be resolved in an effective and timely manner. Standard Occupancy for this property is 4 guests. Each guest above 4 will be charged an additional $50/night.

The Bohemian Bungalow

2 Bedrooms • 4 Guests

$662 night

Welcome to the Bohemian Bungalow! Spiritual Oasis! This is the perfect location for those who have a flair for the healing arts and an eclectic, creative style and sensibility. Be inspired in this 3-bed 2-bath bungalow, full of an array of unique art, crystals, sound tools and a library of both unusual and uncommon plays and books. The owner is an educator in the healing arts and has designed the home for comfort, rejuvenation and shared experiences. Utilize the plethora of pottery, kitchen wares and linens for your meals at home. The open living plan offers plenty of seating for dining and lounging. There is ample space in this Florida bungalow to spend time together or grab a book off the shelf and cozy up for some much-needed alone time. Relax in the front courtyard with the chiminea at dusk and watch the birds. Enjoy the backyard heated pool and the covered patio with convenient dining and lounge areas. Unwind outside and use the BBQ, smoker and firepit to keep warm. The master bedroom is bright yet peaceful, has a king bed, plenty of storage, smart tv and access to the covered patio and pool. The comfortable guest bedroom has a queen bed, and the third room has a desk, a double size futon and access to the BBQ patio. Enjoy this 1600 square foot artisan oasis on a quiet “old Florida” street just a block from the bay and a mile from downtown Sarasota and Sarasota Bay Park & Marina. Master: King 2nd Bedroom: Queen 3rd Bedroom: Office + Double Sized Futon ***We welcome dogs and children with the following caution. The owner has a variety of cataloged crystal trays with small gemstones and minerals throughout the home. You are welcome to peruse and handle them during your visit but please keep watch of your dogs, and/or children as they could be dangerous if swallowed. AMENITIES Private Heated Pool Lush outdoor spaces Outdoor Shower Propane Fire Pit Chimenea Traeger Smoker Full-House Water Filter Beach Supplies: Chairs, Umbrellas, Coolers, Carts & Toys Extra Bedding Extra Towels ART & EDUCATION: Within 1 mile: Ringling Museum Ringling College of Art and Design Asolo Theatre Powel Crosley Estate FSU Sarasota New College Art Center Sarasota Sarasota Garden Club Marietta Museum of Whimsy BEACHES: 5 miles to Lido Beach 9 miles to Siesta Key Beach What’s provided for your stay: Have fun at the beach with chairs, coolers, umbrellas, toys and more, pre-stocked into the villa prior to your arrival. Each residence has their own Property Liaison to ensure any problems or concerns will be resolved in an effective and timely manner. **Minimum Age 25: All Reservations must be booked by and accompanied by an adult who is 25 years of age or older. Valid photo I.D. may be required at the time of booking. **Your inquiry on our property will be responded directly to your personal email. Please keep a lookout for our response so we may best service your request.

Ventana Rosa - 1905

3 Bedrooms • 8 Guests

Aug 25 - Sep 1

$273 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.

Luxury Retreat with Heated Pool, Near Top Beaches & Attractions

3 Bedrooms • 7 Guests

Aug 30 - Sep 6

$296 night

Escape to this newly remodeled pet-friendly Sarasota home featuring a private screened-in heated pool, ping pong table, bikes, games, outdoor grill, beach essentials, and more! Located just minutes from Downtown Sarasota, St. Armands Circle, Lido Key and Siesta Key Beaches—and only 3 blocks from the Sarasota Bay for kayaking, manatee watching, and sunset views. This home includes beach and vacation essentials, and is in a quiet upscale neighborhood. Perfect for families, couples, or small groups looking for sun, fun, and comfort. Prime Location Near Sarasota Hotspots • Minutes to the vibrant Downtown Sarasota with top restaurants, rooftop bars overlooking the Gulf Coast, weekly farmer’s markets, live music and entertainment and just minutes from St. Armand’s Circle, Lido Key Beach, Siesta Key Beach, and Longboat Key • Just 3 blocks from public bay access—perfect for kayaking, paddleboarding, jet skiing, manatee viewing, or sunset views • Easy 7-minute drive from Sarasota-Bradenton (SRQ) Airport Set in Scenic Sapphire Shores • Located in one of Sarasota’s most sought-after neighborhoods, known for its natural beauty and elegant homes • Streets lined with majestic banyan trees, tropical landscaping, and stately waterfront mansions • A peaceful, walkable area perfect for morning strolls and evening sunset walks Private Pool + Outdoor Fun • Screened-in pool with basketball hoop • Outdoor ping pong table and corn hole boards • Pickleball paddles and net, full golf club set, bikes, and board games included Stylish and Modern Living • Recently remodeled with high-end appliances and contemporary finishes • Double over queen bunk bed with desk and chair —ideal for remote work or extra sleeping space • Located in a quiet, upscale neighborhood with multi-million dollar homes Fully Equipped for Beach Days • Pool and beach towels, chairs, beach blanket, cooler, and umbrella provided • Includes boogie boards, pool noodles, kick boards, rafts, buckets, shovels, and a kayak • Spacious and Comfortable Layout Full private access to the entire home • 3 bedrooms, 2 bathrooms, a full kitchen, and an open living area Great for families, couples, or small groups seeking a relaxing Gulf Coast escape. Welcome to Sarasota! One of Florida’s top destinations, known for its white-sand beaches, clear Gulf waters, and vibrant arts and culture scene. Enjoy vibrant downtown Sarasota, waterfront dining, and world-class attractions like St. Armands Circle, The John and Mable Ringling Museum of Art, and Marie Selby Botanical Gardens. Explore the six stunning barrier islands, each with its own charm: • Longboat Key – 12 miles of serene coastline and sea turtle nesting • Lido Key – Three beaches and the vibrant St. Armands Circle • Siesta Key – Voted the #1 beach in the world • Caspersen Beach – Dog-friendly and great for shark tooth hunting • Manasota Key – A nature lover’s paradise with Gulf-to-bay trails • Casey Key – Features an 18-acre park perfect for family outings • After the beach, dive into Sarasota’s arts, dining, and nightlife: • Known as Florida’s Cultural Coast with museums, live performances, and galleries • A variety of dining options, from upscale restaurants with Gulf views to casual seafood spots and lively food festivals Pet Friendly! This is a pet friendly home and allows up to 2 dogs. 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. 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, 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 VR25-00133

Renovated Mid-Century Home with Heated Pool & Yard

Sarasota, Florida, US

Aug 24 - 29

$304 night

Welcome to Sarasota Solitude – A Mid-Century Modern Retreat with a Private Heated Pool, Just Minutes from Siesta Key! Tucked away in a quiet Sarasota neighborhood just 6 miles from the world-famous white sand beaches of Siesta Key, Sarasota Solitude offers the perfect balance of modern comfort, family-friendly amenities, and location convenience. This recently renovated 3-bedroom, 2-bathroom home blends classic mid-century architecture with thoughtful upgrades, creating a stylish and welcoming space for up to six guests. Property Highlights -3BR/2BA with king, queen, and two twin beds (convertible to king) -Private heated pool with safety fence in screened lanai -65" Smart TV, full kitchen, washer/dryer, outdoor grill -Pet-friendly (with fee), sleeps up to 6 -Beach towels, chairs, umbrella, and cooler included -High chair and pack n play available for an additional $10/day. -Smart TVs have been added to bedrooms -Equipped with video surveillance focused on entryways and pool equipment for your peace of mind. Whether you’re shopping and dining at St. Armand’s Circle, exploring the art and culture of downtown Sarasota, or simply soaking in the sun poolside, Sarasota Solitude offers a peaceful and stylish base for your Florida vacation. Other Things to Note: ---------------------------------------- Pet Fee: This is a pet friendly home and allows 1 dog. Please include your pet in your booking so we can make the appropriate arrangements for the departure cleaning. A $125 pet fee is required to help remove pet hair and dander from any furnishings and floors for our future guests. 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, 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! ---------------------------------------- Welcome to Sarasota! One of Florida’s top destinations, known for its white-sand beaches, clear Gulf waters, and vibrant arts and culture scene. Explore six stunning barrier islands, each with its own charm: *Longboat Key – 12 miles of serene coastline and sea turtle nesting *Lido Key – Three beaches and the vibrant St. Armands Circle *Siesta Key – Voted the #1 beach in the world *Caspersen Beach – Dog-friendly and great for shark tooth hunting *Manasota Key – A nature lover’s paradise with Gulf-to-bay trails *Casey Key – Features an 18-acre park perfect for family outings After the beach, dive into Sarasota’s arts, dining, and nightlife: *Known as Florida’s Cultural Coast with museums, live performances, and galleries. *A variety of dining options, from upscale restaurants with Gulf views to casual seafood spots and lively food festivals.

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

$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

Dog-Friendly, Private Pool at Bobby Jones Golf Club

Sarasota, Florida, US

Aug 24 - 29

$320 night

Bobby Jones Golf Club! This dog-friendly 3-bedroom, 2-bathroom pool home is perfect for golf lovers, nature enthusiasts, and anyone seeking a refreshing getaway in a private, welcoming setting. Recently updated with chic coastal decor, this home features an airy open floor plan with elegant wood plank flooring, light-filled interiors, and sophisticated yet cozy furnishings, giving it a blend of Florida charm and upscale comfort. Upon entering, you’re greeted by a spacious living room designed for both relaxation and fun. The large sectional sofa invites you to unwind and enjoy movie nights on the big SMART TV. Sliding glass doors across the back of the home not only allow natural light to flow through but also provide a seamless transition to the stunning backyard oasis, complete with a private pool, lush landscaping, and ample seating. Here, you’ll find sun loungers, chairs, and end tables, creating the perfect setup for soaking up the Florida sun or relaxing with a good book. The gourmet kitchen is a highlight of the home, equipped with gleaming granite countertops, a large island for meal prep or casual dining, and top-of-the-line white appliances, including a gas cooktop. This fully stocked kitchen makes it easy to whip up anything from a quick snack to a family feast. Adjacent to the kitchen, the high-top dining area offers four chairs and an easy-going vibe perfect for casual breakfasts, while a more formal dining area provides additional seating for special meals and gatherings. A small desk and chair with a pool view make it convenient for guests who need to catch up on work or plan the day’s activities. The primary bedroom is a true retreat, offering a plush king-sized bed, a SMART TV, and private access to the pool area, where early risers can slip out for a sunrise swim. The ensuite bathroom has a double vanity, a separate walk-in shower, and a jetted tub, providing a spa-like experience to start or end your day in luxury. Both guest bedrooms are equally inviting, each furnished with comfortable queen beds, SMART TVs, and plenty of closet space. The guest bathroom features a spacious walk-in shower and is conveniently located for easy access from both the living area and the guest bedrooms. Outdoors, the private, fenced backyard offers a serene oasis for relaxation and entertainment. Grill up your favorite meals on the table top grill ( the built-in grill is locked and would require an additional cost to use), or simply lounge by the pool, soaking in Sarasota’s sunny weather. Whether you’re dining alfresco or enjoying drinks under the stars, this space is designed for memorable gatherings with family or friends. One of the biggest perks of this location is its proximity to the iconic Bobby Jones Golf Club. This renowned course is just steps away, offering 18 holes of Championship golf against a scenic backdrop. In addition to golf, the area boasts a beautiful nature park with cycling trails, walking paths, and more for those who enjoy the outdoors. Downtown Sarasota’s shopping, dining, and cultural attractions are also just a short drive away, making this an ideal spot for anyone wanting to explore the best of Sarasota’s beaches, arts scene, and coastal attractions. This vacation rental combines the best of Florida living—comfortable, stylish interiors, a gorgeous outdoor space, and access to world-class golf and outdoor activities. Whether you’re here for a week or a month, this Sarasota retreat is sure to become your favorite escape! Please Note --------------- This is a pet friendly home and allows 1 dog up to 40lbs max or 2 small dogs considered. Please include your pet in your booking so we can make the appropriate departure cleaning arrangements. A $125 pet fee, per pet is required to help with the departure cleaning to remove pet hair and dander from any furnishings and floors for our future guests. 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, and we look forward to hosting you and your pup! About the Bobby Jone’s Golf Club Bobby Jones Golf Club and Nature Park in Sarasota is a local gem that blends challenging golf and serene nature experiences in one picturesque destination. Named after legendary golfer Bobby Jones, this historic club offers 45 holes across three distinctive courses, providing options for golfers of all skill levels. The American and British courses are designed to test and inspire players, with fairways lined by tall trees, scenic water hazards, and natural landscaping that celebrates the Florida environment. Beyond golf, Bobby Jones Golf Club is home to a tranquil Nature Park, offering visitors a chance to enjoy Sarasota’s native flora and fauna. Walking trails wind through lush wetlands and forested areas, providing peaceful spaces to observe local wildlife and migratory birds. The park also features interpretive signage to educate visitors on the area’s ecology and conservation efforts, making it a great spot for nature enthusiasts. Whether you’re a seasoned golfer or someone who simply enjoys nature, Bobby Jones Golf Club and Nature Park offers a relaxing escape just minutes from downtown Sarasota. This unique blend of sport and serenity makes it a beloved destination for both locals and visitors, inviting all to experience the beauty of Florida’s Gulf Coast. City of Sarasota: VR24-00224

Coastal Chic Retreat

$417 night

Nestled in the serene neighborhood of South Gate, Siesta Key, our contemporary 3-bedroom, 2-bath oasis is the perfect blend of comfort and convenience for your dream vacation. Discover the charm of Siesta Key while enjoying the luxuries of a private home. Dog Friendly: We do accept dogs up to 50 lbs. There is a pet fee of $35 per dog per night. Amenities & Features: Sophisticated Interiors: The residence boasts a sleek and modern design, underscored by an open floor plan that ensures the free flow of light and space. Every corner has been thoughtfully decorated with contemporary furniture to make you feel right at home. Restful Sleep: Our three spacious bedrooms are equipped with two lavish king beds and one plush queen bed, providing a peaceful sleep for up to 6 guests. Outdoor Retreat: Step outside to a private pool set against the backdrop of a spacious backyard. The screened-in lanai is perfect for alfresco dinners or a quiet morning coffee, offering a serene space to relax, away from the buzz. Gourmet Kitchen: The large kitchen, fully stocked with modern appliances, makes meal preparations a breeze. Whether you’re planning a quick snack or a sumptuous feast, you’ll find everything you need at your fingertips. Prime Location: Located just 2 blocks from the South Gate Mall, indulge in a delightful shopping spree or pick up essentials from the nearby Aldi grocery store. The beauty of Siesta Key is just a short drive away, offering pristine beaches and a plethora of activities. Additionally, the vibrant Downtown Sarasota, brimming with cultural attractions, eateries, and nightlife, is conveniently close. Stay, Relax, and Explore Whether you’re seeking a peaceful retreat or an adventurous exploration, our South Gate sanctuary is the ideal base. With its blend of modern comforts and prime location, your Floridian vacation awaits. Book today and embrace the sun-kissed allure of Siesta Key and Sarasota! What’s provided for your stay. Have fun at the beach with chairs, coolers, umbrellas, toys and more, pre-stocked into the villa prior to your arrival. Each residence has their own Property Liaison to ensure any problems or concerns will be resolved in an effective and timely manner.

Lido Luxe Estate

Lido Key, FL, US

6 Bedrooms • 12 Guests

Aug 31 - Sep 7

$918 night

Lido Luxe Estate by Lido Key Vacations Vacation Rental License #VR25-00081 Minimum stay duration of 7 days/nights Experience unmatched luxury at Lido Luxe Estate, Sarasota’s finest island retreat located in the prestigious Lido Key! This beautifully appointed six-bedroom, six and a half bath home offers a perfect combination of elegance, privacy, and entertainment. Located just a short six-minute walk from pristine Gulf beaches and the high-end shops and restaurants of Lido Key’s renowned St. Armands Circle, this exquisite estate promises an unforgettable vacation in the heart of Sarasota. Highlights • 6-minute walk to Lido Key Beach • 6 Bedroom / 6.5 Bath • 5 Kings, 2 Twin/ Queen bunks • Rooftop deck • Outdoor putting green • Private pool and spa • Multitude of outdoor games • Outdoor kitchen  • Dedicated office space • Elevator • 6 Parking spaces Enjoy the resort style outdoor living featuring a private heated pool, a 12-person in-ground spa with customizable lighting, and an expansive backyard with a built-in grill and multiple outdoor dining options. The rooftop deck offers stunning panoramic views of Sarasota city lights, and intercoastal waterways. Inside, the gourmet kitchen, complete with a large island and high end appliances, supports memorable dinners or casual gatherings. Multiple outdoor game tables including a deluxe pool table, shuffleboard, corn hole, ping pong, and outdoor TVs elevate the fun, making every moment special. The home boasts a spacious, open concept interior with elegant, high end finishes. The living room offers luxurious seating and a large TV for movie nights. The fully equipped, gourmet kitchen includes a large island, coffee bar and premium appliances, ideal for preparing large meals or hosting friends. The formal dining space supports elegant dinners, while a dedicated office provides a quiet space for remote work or planning your activities. The primary suite features a king-sized bed, a stunning ensuite with a walk-in shower, and a romantic backlit marble wall. The four additional guest bedrooms are furnished with king beds and ensuite bathrooms with walk-in showers, ensuring comfort and privacy for everyone. The sixth bedroom offers twin over queen built in bunk beds, perfect for children or additional guests, complete with an ensuite bathroom. Every bedroom features luxurious bedding, ample storage, and a calming decor. Room Details • Primary Bedroom: King bed, ensuite bathroom with walk-in shower • Second Bedroom: King bed, ensuite bathroom walk-in shower • Third Bedroom: King bed, ensuite bathroom with walk-in shower • Fourth Bedroom: King bed, ensuite bathroom with walk-in shower • Fifth Bedroom: King bed, ensuite bathroom with shower/tub combo • Sixth Bedroom: Two Twin-over-queen bunk beds, ensuite bath with walk-in shower Guests enjoy access to a private pool, in-ground spa, rooftop deck, outdoor kitchens, game rooms, and organized outdoor activities. This rental is great for large family gatherings or corporate retreats. Parking accommodates up to six cars, with no overnight parking beyond that. The property is pet free and family friendly, with all the amenities needed for a luxurious and relaxed Sarasota vacation. Book your stay at Lido Luxe Estate today and indulge in a luxury waterfront retreat that combines coastal elegance with outdoor extravagance. Relax by the pool and spa, enjoy picturesque sunsets from the rooftop, or explore Lido Key’s world-famous beaches and vibrant shopping districts. Reserve now and create lasting memories! - This home is managed by Lido Key Vacations. This property does not allow pets of any kind.  6 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 Lido Key Vacations 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.

Brisas Del Mar - 3515

$419 night

🌴 Brisas Del Mar | Private Pool with Spa, Guest House, Near Siesta Key Beach 💖 Why You’ll Love This Home Brisas Del Mar offers a well-designed Siesta Key stay with a main house and private guest house, creating a flexible layout for groups who want shared spaces along with added privacy. Located just 2 miles from Siesta Key Beach, this home combines indoor comfort with a fully equipped outdoor setup. The backyard centers around a private pool with a waterfall feature and in-ground spa, surrounded by lounge seating and a covered patio with an outdoor TV. A full outdoor kitchen and dining area make it easy to gather for meals, while the guest house provides a separate retreat for part of your group. Additional features like a pool table and bicycles add variety to your time at home. 👨‍👩‍👧 Perfect For Families, multi-generational groups, or friends traveling together who want a mix of shared living space and private accommodations. 🎞️ Imagine This Head out for a beach day at Siesta Key Beach, then return home to spend the afternoon around the pool. Move between the shaded patio and lounge seating while others gather at the outdoor kitchen to prepare a casual meal. Inside, the layout offers multiple places to spread out, whether it’s a game of pool, a movie night in the main living area, or downtime in the additional den. The separate guest house allows part of the group to have their own space while still staying connected. As the day winds down, gather for dinner indoors or outside before settling in for the evening. 🛌 Where You’ll Sleep Main House • Bedroom 1: King Bed, Ensuite Bathroom with Double Vanity and Walk-In Shower • Bedroom 2: King Bed • Bedroom 3: Queen Bed • Hall Bathroom: Full Bath with Pool Access Guest House • Bedroom 4: Two Queen Beds, Ensuite Bathroom with Walk-In Shower Additional Sleeping • Sleeper Sofa in Secondary Living Area Accommodates up to 10 guests 📍 Explore the Area • 2.0 Miles to Siesta Key Beach – Access to Sand and Gulf Waters • 2.0 Miles to Siesta Key Village – Dining, Shopping, and Entertainment • 3.8 Miles to Crescent Beach – Shelling, Snorkeling, Sunbathing • 4.0 Miles to Downtown Sarasota – Bayfront Parks, Arts, and Restaurants • Free Island Trolley – Easy Transportation Around Siesta Key ⌛ Book Today A favorite for groups seeking both shared spaces and private accommodations, Brisas Del Mar offers a flexible layout in a convenient Siesta Key location. Your reservation includes enhanced cleaning protocols and a 35-point post-clean inspection for peace of mind throughout your stay. 🔎 Need to Know Per City of Sarasota regulations, this property requires a minimum rental period of 7 nights. The maximum occupancy is 10 per the City’s occupancy limit. This home includes a private guest house accessible from the pool area, offering a separate living space for added privacy. This property has an active Ring doorbell and additional video surveillance on pool equipment only. Starter packs of kitchen and toiletry essentials are provided for your first couple of nights. Free high-speed WiFi is included. 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.

Blue Palm

Lido Key, FL, US

4 Bedrooms • 8 Guests

Aug 26 - Sep 2

$432 night

Blue Palm by Lido Key Vacations Minimum stay duration of 7 days/nights #VR22-00132 Blue Palm by Lido Key Vacations is a stylish, single-level coastal retreat offering the perfect blend of walkable convenience and private relaxation. Ideally located just two blocks from Lido Beach and steps from the boutiques, restaurants, and nightlife of St. Armands Circle, this four bedroom, three bath home is designed for effortless Lido Key living. With a private heated pool, screened lanai, and inviting indoor spaces, Blue Palm is an ideal choice for families, couples, or friends seeking a boutique Sarasota beach escape. Highlights • 8-minute walk to Lido Beach • 4 bedrooms / 3 bathrooms • 3 king beds, 2 twin beds • Private heated pool • Screened lanai with seating • Outdoor dining area with BBQ grill • Beach chairs, beach wagon, and cooler provided • 4 bicycles for guest use • Dog friendly with approval and additional fee • Washer and dryer • 4 Parking spaces • 6-minute walk to St. Armands Circle • 18-minute walk to Ted Sperling Park The private backyard at Blue Palm is a tropical retreat designed for relaxation. Cool off in the sparkling heated pool, unwind on poolside loungers, or enjoy meals prepared on the BBQ grill in the outdoor dining area. The screened lanai offers a shaded escape for morning coffee or evening refreshments, creating a peaceful setting to enjoy the island breeze throughout your stay. Step inside to a bright, open concept layout filled with natural light and views of the backyard. The fully equipped kitchen features a farmhouse sink and generous counter seating, making it ideal for casual breakfasts or evening gatherings. The living and dining areas provide comfortable seating for movie nights, shared meals, and quality time together after a day at the beach. The primary bedroom is a serene retreat with a king bed and an ensuite bathroom featuring a walk-in shower. The laundry room is conveniently accessed through the primary ensuite. The second bedroom also offers a king bed and a private ensuite bathroom with a walk-in shower. The third bedroom features a king bed and access to a hallway bathroom with a shower and tub combination, while the fourth bedroom includes two twin beds and shares the same hallway bathroom. Each space is thoughtfully designed to ensure restful nights and relaxed mornings. Room Details • Primary Bedroom: King bed, ensuite bathroom with walk-in shower, washer and dryer access • Second Bedroom: King bed, ensuite bathroom with walk-in shower • Third Bedroom: King bed, hallway bathroom with shower and tub combination • Fourth Bedroom: Two twin beds, hallway bathroom with shower and tub combination Guests have access to four bicycles, a beach cart, beach chairs, and a cooler, making trips to the beach simple. Spend your days exploring St. Armands Circle, home to upscale boutiques, cafes, dessert shops, and fine dining, or venture to nearby attractions such as Mote Marine Aquarium, Sarasota Bayfront, fishing charters, and sunset cruises. Parking is available for up to four vehicles. Experience relaxed coastal elegance at Blue Palm by Lido Key Vacations, where a prime walkable location, private heated pool, and thoughtfully designed living spaces create the perfect Sarasota getaway. Book your week today and discover boutique beach living on Lido Key! LOVE This Home? Take a look at these other Lido Key properties in this Owner’s Portfolio! • Reel Me In • Vitamin Sea • All Decked Out

Sleeps 8 • Private Pool • Dog Friendly • Balcony

Aug 30 - Sep 1

$162 night

This 3-bedroom home is in a prime location & has EVERYTHING you need for an amazing vacation in Sarasota, FL! • Private Pool • Outdoor Patio • Private Balcony • Board & Card Games • Fully Stocked Kitchen • Drip & Keurig Coffee Maker • Plush Beds • High Speed WIFI • Family Friendly - High Chair & Pack ’n Play • Washer & Dryer • Dog Friendly • Ample Parking Welcome to your Sarasota getaway! This beautifully appointed home offers the perfect blend of comfort, style, and convenience for families and groups alike. With 3 spacious bedrooms, 2.5 bathrooms, and room to accommodate up to 6 guests, you’ll have plenty of space to relax, unwind, and make unforgettable memories. Step inside to enjoy bright, airy living spaces, a fully equipped kitchen, and cozy gathering areas perfect for movie nights or game time. Outside, soak up Florida’s sunshine while enjoying the backyard retreat, or take a short drive to explore Sarasota’s world-famous beaches, cultural attractions, and dining scene. Whether you’re planning a family vacation, a couples’ getaway, or a trip with friends, this Sarasota gem is designed for comfort and connection. MAIN SPACES OF THE HOME: – 3 BEDROOMS & 2.5 BATHROOMS – BEDROOM 1: * 2 Twin-sized Bed * Nightstand and Lamp * Ceiling Fan * Ensuite Bathroom BEDROOM 2: * King-sized Bed * Smart TV * Nightstand and Lamps * Ceiling Fan * Direct Outdoor Access * Ensuite Bathroom BEDROOM 3: * Queen-sized Bed * Smart TV * Nightstand and Lamp * Direct Balcony Access – 2.5 BATHROOMS – * Ensuite Bathroom with Walk-in Shower * Ensuite Bathroom with Walk-in Shower * Half Bathroom – CHEF’S KITCHEN – * Fully Stocked * High-end Appliances * Large Refrigerator * Ample Cabinetry * Large Island w/ High Seating * Coffee Maker: Drip & Keurig – LIVING ROOM – * Smart TV * Large Plush Sofa + Seating * Expansive Windows * Board & Card Games * Ceiling Fan * Open Floor Plan 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. - An exterior camera is installed solely to monitor our cleaning team for quality and security purposes. - Parking in the driveway for 8 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 21 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.

Sarasota House w/ Private Pool - 4 Mi to Beach!

2 Bedrooms • 4 Guests

$236 night

Whether you're looking to spend time by the pool or at the beach, 'Siesta Jewel’ is perfect for travelers on a memorable Floridian adventure and snowbirds seeking to escape the winter! Lounge in the home’s pleasant lanai or prepare a delicious meal on the patio’s gas grill. This 2-bedroom, 2-bathroom Sarasota vacation rental is also located in a quiet neighborhood just minutes away from golf courses, Marie Selby Botanical Gardens, Bayfront Park, and some of America's most beautiful beaches! -- THE PROPERTY -- Lanai | Gas Grill | Quiet Neighborhood | 4 Mi to Marie Selby Botanical Gardens | Near Golf Bedroom 1: King Bed | Bedroom 2: King Bed OUTDOOR LIVING: Private outdoor pool, pool toys, lounge seating, patio, beach chairs/umbrellas, boogie boards INDOOR LIVING: Flat-screen TV w/ cable, leather sofa, ceiling fans, en-suite bathroom KITCHEN: Stove/oven, refrigerator, microwave, dishwasher, dishware/flatware, cooking basics, coffee maker, Crockpot, toaster, blender, expansive counters, breakfast bar GENERAL: Free WiFi, central air conditioning, towels/linens, washer/dryer, laundry detergent, hair dryer, trash bags/paper towels, keyless entry ACCESSIBILITY: Single-story home, 1 step to enter FAQ: Quiet hours starting at 9:00 PM, 2 exterior security cameras (facing out), optional nightly pool heat fee (paid pre-trip, applied to entire stay) PARKING: Garage (2 vehicles), driveway (2 vehicles), street parking (first-come, first-served) -- THE LOCATION -- SAND & SUN: Public Beach Access (4 miles), Crescent Beach (5 miles), Sarasota Beach (6 miles), Siesta Beach (6 miles), Indian Beach Park (7 miles), Lido Key Beach (8 miles) ATTRACTIONS: Marie Selby Botanical Gardens Downtown Sarasota (4 miles), Bayfront Park (4 miles), Mote Marine Laboratory & Aquarium (8 miles) GOLF: Village Green Golf Club (1 mile), The Palms Golf Club at Forest Lakes (2 miles), Bobby Jones Golf Club (5 miles), The Highlands Golf Course (7 miles), The Groves Golf Course (7 miles) DAY TRIPS: Walt Disney World Resort (119 miles), Universal Studios Florida (126 miles) AIRPORT: Sarasota Bradenton International Airport (8 miles) -- 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 - No pets allowed - 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 - NOTE: This single-story home requires 1 step to enter - NOTE: Your safety matters. This property features a Ring doorbell device with an exterior security camera facing the street, and a Ring spotlight exterior security camera located on the garage facing the street. The cameras do not look into any interior spaces. The doorbell camera records video and sound for 30 seconds when motion is detected by the device. The spotlight camera will turn on the spotlights and walkway lights for 3 minutes when activated by motion; it will also record video and sound for 60 seconds - NOTE: Please observe quiet hours after 9:00 PM - NOTE: There is an optional pool heat fee of $35/night (+ fees & taxes, paid pre-trip, applied to entire stay)

Siesta Dolce - 3750

4 Bedrooms • 6 Guests

Aug 24 - 26

$827 night

Welcome to Siesta Dolce, a stunning vacation rental home located on the breathtaking island of Siesta Key, known for its unparalleled beauty and pristine white sandy beaches. This luxurious 3-bedroom, 2-bathroom home is the epitome of relaxation and comfort. As you step inside, you’ll be greeted by a spacious living area adorned with tasteful coastal decor and ample seating for your family or group of friends. The large windows fill the home with natural light and provide a glimpse of the lush tropical foliage outside. Siesta Dolce features a Florida room where you can curl up with a good book or simply take in the view of the pool area.The kitchen is fully equipped with modern appliances and all the essentials you need to prepare your at home meals on vacation.Additionally, this property features three spacious bedrooms with two king-sized remote adjustable beds and two twin beds, comfortably accommodating up to six guests. Linens are provided for a hassle-free stayOne of the highlights of Siesta Dolce is the private heated pool, which beckons you to take a refreshing dip or simply lounge by the water. The pool area is complete with comfortable outdoor seating and a fire pit, perfect for enjoying your morning coffee or a cocktail at sunset. Siesta Dolce’s location is unbeatable, with Siesta Key Public Beach Access #2 and Siesta Key Village both less than 2 miles away. Siesta Key Public Beach is consistently rated as one of the best beaches in the United States, with its soft, powdery sand and calm Gulf of Mexico waters. Siesta Key Village is a quaint and vibrant area, with an array of shops, restaurants, and nightlife options to explore.Whether you want to soak up the sun on the beach, relax by the pool, or explore the charm of Siesta Key Village, Siesta Dolce is the perfect vacation rental home for your next getaway. Come experience the beauty of Siesta Key and make unforgettable memories at Siesta Dolce!Exclusive Amenities Include:• Private Heated Pool• Fire Pit• Less Than 2 Miles To Siesta Key Public Beach Access #2• Less Than 2 Miles To Siesta Key Village• 3 Bedrooms, 2 Full Bathrooms• 2 King Beds & 2 Twin Beds (Sleeps 6) with linens provided• Remote Adjustable King Beds (2)• Spacious Outdoor Lounging Area• Florida Room w/ Seating Area• Private 2 Car Garage• Free WiFi & HDTV’s• 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• Gas Grill• Enhanced cleaning protocols provided by our CottageClean Team• Island Shuttle Transportation Available• Dog-Friendly with a Fee (1 dog up to 25lbs, not quoted in price & charged after approval)Siesta Dolce can accommodate up to 6 guests with a bedding configuration as follows:• Bedroom # 1: King Bed (1) – Sleeps: 2• Bedroom # 2: King Bed (1) – Sleeps: 2• Bedroom # 3: Twin Bed (2) – Sleeps: 2We 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: This property is registered as a vacation rental with the City of Sarasota with a Registration Number of VR23-00018. 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 8 guests. This pool is heated from November 15th to April 15th.

Shore Thing - 185

5 Bedrooms • 10 Guests

Aug 29 - Sep 5

$485 night

Imagine waking up in your own private coastal retreat. At Shore Thing, island serenity meets modern luxury—your dream Siesta Key escape begins here. Welcome to Shore Thing—your private slice of paradise in the heart of Siesta Key. This newly renovated home was thoughtfully curated for your comfort where upscale comfort meets laid-back beach living, Your just a 5-minute drive to the world-famous Siesta Key Beach. As you step into the backyard, prepare to be transported. A sprawling resort-style pool shimmers under the Florida sun, bordered by lush tropical landscaping and swaying palms. Whether you’re floating in the crystal-clear water, enjoying the soothing spillover hot tub, or sipping cocktails by the fire pit, this outdoor oasis was designed for unforgettable moments. Evenings are best spent under the stars, sharing laughter around the propane fire feature or enjoying a sunset dinner on the covered patio. The backyard seamlessly connects to the interior, offering a true indoor-outdoor living experience. Inside, Shore Thing offers the ideal layout for families or groups traveling together: • Three private master suites, each with spa-inspired en-suite bathrooms and direct access to the outdoor area. • A fourth bedroom with a private lounge area behind sliding glass doors—perfect for quiet reading or morning yoga. • A fifth bedroom with a twin-over-full bunk setup—ideal for kids or teens. At the heart of the home is a chef-ready kitchen with modern appliances and everything you need to cook, dine, and entertain. Start your day with coffee from either the classic drip machine or Keurig, then enjoy a breezy breakfast outdoors as the palms rustle overhead. Each bedroom—aside from the bunk room—is equipped with a large Smart TV, making it easy to unwind after beach days or poolside lounging. Explore the charm of Siesta Key Village, just minutes away, where you’ll find boutique shops, waterfront dining, and lively coastal nightlife. Whether you seek adventure, relaxation, or quality time with loved ones, Shore Thing delivers the full island experience. Don’t miss your chance to stay at one of Siesta Key’s most captivating private homes. Book your stay at Shore Thing today and create lasting memories in your own tropical paradise—steps from the beach and a world away from ordinary. Shore Thing Siesta Key | 5BR home w/ pool, hot tub & fire pit. Book your luxury island escape today! Shore Thing can accommodate up to 10 guest with a bedding configuration as follows: Bedroom #1: Queen Bed (1) sleeps 2 Bedroom #2: King Bed (1) sleeps 2 Bedroom #3: King Bed (1) sleeps 2 Bedroom #4: Queen Bed (1) sleeps 2 Bedroom #5: Twin bed (1) and a Full Bed (1) sleeps 3 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: The Spa is heated from November 15th to April 15th. This property is registered as a vacation rental within the City of Sarasota with the Registration Number VR25-00056. Due to the City of Sarasota vacation rental code, this property can only be rented once during a seven (7) day period and has a maximum occupancy of 10 guests.

Casa Leone - 3446

$478 night

Casa Leone | Heated Pool & Spa, Pet Friendly, Putting Green Why You’ll Love This Home Tucked on the northern end of Siesta Key, Casa Leone is a four-bedroom retreat where polished interiors meet a private outdoor oasis. The heated pool and spa, screened lanai, putting green, and upper deck lounge area give everyone plenty of ways to fill the day, with Siesta Key’s world-famous beach and village just a short drive away! Perfect For Families, multi-generational groups, or friend gatherings looking for a well-appointed Siesta Key home with private outdoor amenities and room for up to 10 guests. Imagine This Morning starts in the open-concept kitchen, coffee brewing while sunlight fills the living room just off the pool. Slide open the door and the screened lanai becomes your breakfast spot, island breezes drifting through while the kids claim their pool floats. Afternoons shift between the putting green, a spirited ping pong match, and the upper deck lounge chairs where the breeze picks up and the neighborhood stretches out below. When dinner rolls around, Siesta Key Village is a short drive away, grab a table or bring something back to enjoy al fresco. Evenings settle into movie nights on the flat-screen or quiet time on the king suite’s private balcony, the neighborhood still and cool around you. Where You’ll Sleep • Bonus Room: Sleeper Sofa, 1st Floor, Full Bath, TV • Bedroom 1: Queen Bed, 1st Floor, Bonus Room Bath, TV • Bedroom 2: Queen Bed, 2nd Floor, Hallway Bath, TV • Bedroom 3: Queen Bed + Twin/Twin Bunk Bed, 2nd Floor, Hallway Bath, TV • Bedroom 4: King Bed, 3rd Floor, Ensuite Bath, Private Balcony, TV Explore the Area • 2.2 Miles to Siesta Key Village — Dining, Shopping, and Nightlife • 3.0 Miles to Siesta Key Beach — Powdery Quartz Sand and Crystal-Clear Water • 3.5 Miles to Downtown Sarasota — Arts, Culture, and Waterfront Dining • 6.4 Miles to St. Armands Circle — Upscale Boutiques and Waterfront Dining Don’t wait From the putting green to the screened lanai, Casa Leone is designed for days that feel effortlessly unhurried — and every stay is backed by our CottageClean™ program: a 6-hour deep clean and 35-point inspection. Please Note This property is registered as a vacation rental with the City of Sarasota, Registration No. VR22-00008. Per City of Sarasota code, this property may only be rented once per seven-day period with a maximum occupancy of 10 guests. The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. 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.

Hemingway House - 117

3 Bedrooms • 8 Guests

$279 night

🌴 Hemingway House | Screened Lanai + Heated Pool 💖 Why You’ll Love This Home This thoughtfully updated island retreat blends laid-back coastal charm with stylish indoor-outdoor living. Enjoy coffee in the screened lanai, pizza nights by the wood-burning oven, and breezy evenings around the private heated pool—all just 2.1 miles from Beach Access 5 and a short drive to Siesta Key Beach. 👨‍👩‍👧 Perfect For Families or small groups who want a quiet, design-forward escape with private amenities and fast access to Siesta Key’s best beaches. 🎞️ Imagine This You start the morning with a cup of fresh coffee from the built-in GE Café Keurig, stepping into the screened lanai as soft island breezes drift through the palms. After sun-soaked hours at Siesta Key Beach, you cool off in the private heated pool, rinse off in the spa-style outdoor shower, and prep hand-tossed pizzas in the Mediterranean wood-burning oven. As stars begin to glow overhead, you dine alfresco under string lights, then wind down indoors with plush linens and cozy spaces made for total relaxation. 🛌 Where You’ll Sleep • Bedroom 1: King Bed, Ensuite Bath, Second Floor, TV • Bedroom 2: Queen Bed, Shared Bath, Second Floor, TV • Bedroom 3: Full Bed, Shared Bath, Second Floor, TV • Living Room: Sleeper Sofa – Shared Bath Access 📍 Explore the Area • 2.1 Miles to Beach Access 5 – A Local Favorite for Shelling and Sunrise Walks • 3.0 Miles to Siesta Key Main Beach – Iconic White Sand and Family-Friendly Vibes • 3.2 Miles to Siesta Key Village – Shops, Restaurants, and Open-Air Cafés • 0.5 Miles to Gulf Gate Dining District – International Cuisine and Local Eateries • 1.6 Miles to Crescent Beach – Quieter Sands and a Relaxed Coastal Feel • Located on the Peaceful North End of Siesta Key – Ideal for Tranquil Mornings and Easy Exploration ⌛ Don’t Wait This home books quickly. Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection—so you arrive at a home that feels fresh, spotless, and ready for your vacation. 📌 Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. Free high-speed WiFi is included. This home is registered with the City of Sarasota (VR22-00099). Per city code, rentals require a 7-night minimum and a maximum of 8 guests. All bedrooms are located on the second floor. If stairs or mobility concerns apply, contact us directly for personalized recommendations.

Sunset West - 3360