Holiday rentals with a pool in Sarasota Springs

The outdoor pool area features a heated pool and spa, surrounded by a screened lanai. Lounge chairs are positioned nearby for relaxing. A hammock rests on the grass, inviting moments of leisure. Lush greenery enhances the tranquil environment.

4.95 out of 5 average rating, 106 reviews

Deja Blue Villa Salt Water Heated Pool & Spa

Featured Home: 🌊 Deja Blue Villa 🌊 From the beautiful, fully-equipped kitchen, to our fenced and heated pool patio, Deja Blue Villa is your perfect vacation home! Located only 20 minutes from Siesta Key Beach and 25 minutes from Lido Key Beach, this incredible stay includes: Private Heated Pool & Spa + Lounge Chairs & String Lights Pool Patio Mini Fridge + Serving Area Free Washer/Dryer Access, Detergent & Softener Included Gas Grill + Propane Coffee & Coffee Maker TV + Roku in Every Bedroom

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4.91 out of 5 average rating, 129 reviews

Coastal Farmhouse - 3/2 with heated saltwater pool

Experience relaxation at this tranquil 3BD/2BA home with a heated pool, perfect for a family retreat! Prepare meals in the fully equipped kitchen or savor local delights on the screened-in lanai. Each bedroom boasts plush bedding, ensuring a restful night's sleep. Plus, a cozy living room. Conveniently located, just under 9 miles from Siesta & Lido Key Beach, Der Dutchman 2.2 miles and 2.5 miles from Yoder's Restaurant. Shopping and dining options at University Town Center, only 7.7 miles away.

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An outdoor dining area features a wooden table set for four, overlooking a pristine pool. Lounge chairs are positioned nearby, providing a relaxing space for sunbathing. The screened patio ensures comfort while enjoying meals or relaxation outdoors.

4.98 out of 5 average rating, 162 reviews

Heated Pool Oasis 3BR/2BA near Siesta Key Beach

Relax at this modern heated pool house located just 15 min from the famous Siesta Key Beach. Nested in a quiet neighborhood with a lot of privacy, the house has plenty of space for an entire family or a group of friends. An additional family room with a TV for kids. Relax by the pool in the spacious outdoor area or explore the beautiful downtown filled with restaurants. Recently renovated, this home offers handmade authentic Mexican tile flooring to compliment a cozy and contemporary design.

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A serene view of the pool area features clear blue water, framed by a brick border. Lush greenery surrounds the pool, with a statue placed amidst the landscaping. Sunlight filters through the trees, casting soft reflections on the water's surface.

4.98 out of 5 average rating, 129 reviews

The Oasis

Welcome to The Oasis, your Florida home away from home! Centrally located, between siesta key and st Armand’s circle, near many fantastic restaurants, grocery stores, and downtown. This home has everything you need for a fantastic stress free stay in Sarasota. A luxurious Italian style pool and garden area, a spacious indoor area with a full sized kitchen, king bed, queen bed, 2 twin beds and 2 twin air mattress. 3 smart tvs. We love this stunning and cozy home and we’re sure you will too!

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A covered patio area features modern wicker furniture with white cushions, positioned around a glass coffee table. The inviting space overlooks a pristine pool, surrounded by a protective screen. Lush greenery is visible in the background, enhancing the tranquil setting.

4.96 out of 5 average rating, 154 reviews

Luxury Pool Family Oasis-Siesta Key/DT 3BR/2BA

Welcome to your home away from home! This renovated, spacious, and bright pool home will immerse you in a luxurious experience the minute you arrive. Located on a lush, quiet street, yet close to all of Sarasota's best attractions! Close to Siesta Key Beach (#1 beach in the USA), 10 minutes to downtown (with fantastic restaurants and shopping), and within walking distance of the famous Fresh Fish Waltz Market. Easy I-75 access, Nathan Benderson Recreational Lake Park, and the new UTC mall!

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A swing chair hangs from the ceiling in a cozy living space, complemented by a dark sectional sofa and a round coffee table. A decorative rug adds warmth to the wooden floor, while a wall-mounted television and a piece of artwork provide visual interest.

4.8 out of 5 average rating, 189 reviews

1 House 1400sq. ft. 12 min from Siesta Key!

12 min. from Siesta Key Beach!! Perfect cozy vacation home in quiet, friendly neighborhood. Central to lots of shopping/restaurants. 1-king, 1-queen, bunk beds w/ 1-full & 1-twin. Dog & cat friendly w/ large private fenced yard, & 1-men's & 1-women's bike. Air hockey table w/ board games & pool toys. Fully loaded kitchen & W/D. Spacious living w/ large sectional, swing chair, & all bedrooms come w/ TVs & free Netflix & Hulu. Looking forward to hosting you! Message me anytime w/ questions.

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The exterior of a newly renovated home is shown, featuring a light-colored brick facade and a modern garage door. A well-maintained driveway leads to the entrance, which is accentuated by a bright orange door. Landscaping includes gravel beds and low-maintenance plants amidst partial cloud cover.

4.88 out of 5 average rating, 103 reviews

Gorgeous renovation with pool, minutes from beach

Light, bright and newly renovated. Beautifully decorated 3 bedroom home minutes from Siesta Key and downtown. The spacious modern kitchen has a slider that leads to covered porch and large pool with private fenced yard. A second slider from the porch leads to the master bedroom with master bath and walk in closet. Open living room and 2 additional big bedrooms make the house perfectly comfortable for 6. Everything you need is right here! Siesta Key Beach Distance - 16 Min; 6.1 Mi

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4.98 out of 5 average rating, 96 reviews

GARDEN VIEW HOUSE WITH A POOL

Relax with the whole family at this peaceful place to stay. Private Garden Front Home. Located 7 miles to the Siesta Key, #1 beach in United States. 1 mile to Legacy Trail. Trail is 18.5 mile Connecting Sarasota and Venice, Florida. This 3 bedrooms 2 bath home offers everything you need for your next vacation getaway! The kitchen is equipped with everything needed to make your favorite home-cooked meals and host the family at the table or on the covered outdoor screened-in lanai!

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A private heated pool is enclosed within a screened area, featuring clear blue water. Red Adirondack chairs are positioned nearby on a structured surface. A spacious yard is visible beyond the pool area, enclosed by a wooden fence for added privacy.

4.82 out of 5 average rating, 230 reviews

Heated Open Pool Home In Sunny Sarasota!

This home is perfect for hosting friends and family or just relaxing on your own! Spend a day in the surf and sun at the world famous Siesta Beach, shop at one of the many centrally located shopping centers , try local restaurants, or just take it easy in your own private and open pool and sitting area! Like making your own meal, step inside to an updated and fully stocked kitchen! Two living rooms, lots of space. Let this beautiful home be yours during your visit to Sarasota!

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A heated saltwater pool is framed by a privacy fence, with lounge chairs positioned nearby. Lush palm trees add greenery to the space, creating an area for relaxation. The clear water reflects the sky, enhancing the tranquil ambiance of the outdoor setting.

4.85 out of 5 average rating, 221 reviews

~Flamingo House~3 br,3 bath, heated pool~

Welcome to The Flamingo House with beautiful private pool area surrounded by privacy fence and palms. Take a short drive to beautiful Downtown Sarasota or Marina Jack for the sunset. Plus Legacy Trail is accessible from our street w/Pompano Pickleball court close by. Ice cream, coffee shops and restaurants are within 5 minutes. Situated on a quiet street while still being close to main roads, and an easy 20 minutes to Siesta Key and Lido Key beaches,5 minutes to Pinecraft.

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4.93 out of 5 average rating, 43 reviews

Quiet Family Home w/ Pool Near Pinecraft

Escape to a serene family retreat near Pinecraft and Yoders! This 3-bed, 2-bath home features a screened-in heated swimming pool for year-round enjoyment. Nestled in a quiet, family-friendly neighborhood, savor nearby Amish dining at Yoders and Der Dutchman. Siesta Key & Lido Key Beaches are only 8.7 miles away! Explore Marina Jack's at Bayfront Park in downtown Sarasota, where you can admire stunning boats and enjoy a leisurely stroll. Your perfect vacation awaits you!

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4.9 out of 5 average rating, 10 reviews

4 Bedroom/5 Bed/2 Bath- Tyne Haven +Saltwater Pool

Enjoy your Sarasota getaway at Tyne Haven! Relax in a clean, comfortable home with a private pool and patio. You’re a short drive from Siesta Key, Lido Key, Downtown Sarasota, Pinecraft, and St. Armands, so it’s easy to get out and explore when you feel like it. We’re always here if you need anything to help your stay go smoothly. Hope Tyne Haven feels like your home away from home while you’re in Sarasota.

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Popular amenities for Sarasota Springs rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A serene outdoor space is highlighted by a heated saltwater pool and a six-person spa. Comfortable lounge chairs line the pool area, and an outdoor grill is situated nearby. The setting is complemented by a vibrant sunset, enhancing the tranquil atmosphere.

5.0 out of 5 average rating, 110 reviews

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

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4.86 out of 5 average rating, 43 reviews

Entire Family Home in Sarasota with a Heated Pool

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5.0 out of 5 average rating, 22 reviews

Private Heated Pool, 8.5mi to Siesta Key Beach

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5.0 out of 5 average rating, 11 reviews

Sunny Palm Villa

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A heated pool is surrounded by lush greenery, featuring six lounge chairs and a large umbrella for shade. The patio area is accentuated with tropical plants, while a covered lanai is visible in the background, providing additional outdoor space.

4.99 out of 5 average rating, 100 reviews

Your Private Tropical Paradise — Monthly Stays

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4.81 out of 5 average rating, 16 reviews

Le Palm House • Pool • Near Siesta

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A screened-in pool area features a clear blue pool with a shallow entry. Sun loungers are positioned alongside the pool, and outdoor seating is arranged nearby. The space is bathed in natural light, creating an inviting atmosphere for relaxation.

4.84 out of 5 average rating, 62 reviews

[The Island Date Home]Heated Pool•Family Friendly•

LocationFamilyBack garden

A spacious kitchen and dining area features a large island with bar seating, complemented by a dining table that accommodates multiple guests. Natural light illuminates the room through large windows, while neutral tones and wood accents create a welcoming atmosphere.

5.0 out of 5 average rating, 47 reviews

Sarasota Paradise/Stunning Home/Heated Pool

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Apartment rentals with a pool

Apartment in Gulf Gate Estates

A modern living area features a blue sofa with decorative pillows and a low coffee table. A dining set with white chairs is visible in the background. Bright natural light filters through sheer curtains, enhancing the neutral grey walls and stylish artwork.

Heated Pool Apartment Near Siesta Key | 1BR

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4.87 out of 5 average rating, 157 reviews

The exterior of the condo displays a modern design with a light color palette. Palm trees are positioned around the landscaped area, and two garages are visible, along with a walkway leading to the entrance. The sunny sky enhances the welcoming appearance of the property.

4.85 out of 5 average rating, 110 reviews

Comfy Siesta Key Condo

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4.92 out of 5 average rating, 172 reviews

Apartment in Sarasota

Cottage on Siesta Key Beachside & Stunning sunsets

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A modern living area showcases a comfortable sectional sofa and armchair, complemented by a wooden coffee table. A large flat-screen TV is positioned on a media console. Natural light floods the space through sliding glass doors that lead to a balcony, enhancing the open feel.

4.88 out of 5 average rating, 179 reviews

Spacious 2-Floor, 2BR, 2.5BA Condo Near Everything

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A modern dining area is highlighted by a marble table with an elegant vase and tableware arranged for a meal. Stainless steel appliances and a large television are visible in the background, with natural light flowing in from sliding glass doors leading to an outdoor space.

4.88 out of 5 average rating, 146 reviews

Crystal House on Siesta Key Beach

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4.96 out of 5 average rating, 164 reviews

A bright and airy living space features a modern sofa facing a sleek coffee table. The open kitchen is visible in the background, showcasing white cabinetry and bar seating with stylish stools. Light fills the room through large windows, enhancing the spacious feel.

Apartment in Sarasota

Modern Coastal Oasis - Beach and Private Patio

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4.96 out of 5 average rating, 141 reviews

Siesta Key Condo. Checkout our great rates!

ValueFamilyAccuracy

4.82 out of 5 average rating, 154 reviews

Apartment in Lido Key

LIDO KEY 1 BR/1Bath Heated Pool 16

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Other holiday rentals with a pool

4.88 out of 5 average rating, 26 reviews

Hope Haven | Private Heated Pool + Backyard Oasis

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4.99 out of 5 average rating, 92 reviews

The Cottage at the Roost, SRQ Ranch Paradise

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4.89 out of 5 average rating, 61 reviews

Pet-Friendly Pool Oasis Near Siesta Key Beaches

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4.95 out of 5 average rating, 66 reviews

Beautiful Oak View Manor - Siesta & Legacy Trail

LocationFamilyBack garden

4.95 out of 5 average rating, 63 reviews

A private heated pool is surrounded by a spacious patio with lounge chairs and an umbrella for shade. The modern two-story home features large glass doors that brighten the living spaces, and vibrant greenery enhances the outdoor area.

Home in Arlington Park

Private Heated Pool Retreat for Two Families

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5.0 out of 5 average rating, 29 reviews

Heated Pool + Games | 15 Min to Siesta Key

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The exterior of the home is shown, featuring a neatly landscaped yard with various plants and palm trees. A two-car garage with a dark door is visible, alongside a paved driveway leading to the entrance. The evening sky displays soft colors as daylight fades.

5.0 out of 5 average rating, 12 reviews

Woodhaven Retreat

LocationFamilyIndoor spaces