Vacation rentals with a pool in Fruitville

An outdoor area features a heated pool surrounded by a spacious deck. Lounge chairs are positioned nearby for relaxation, and a dining set offers seating for outdoor meals. A screened enclosure provides protection from insects while allowing natural light to filter through.

4.91 out of 5 average rating, 138 reviews

Heated 3BR Pool Home Glen Oaks | Close to Downtown

Family-friendly pool home near Bobby Jones Golf Club, perfectly located in the heart of Sarasota. You’re less than 10 minutes from top attractions, dining, and shopping, Downton Sarasota and just a short drive to the world-famous Siesta Beach or Lido Beach. This private home features its own entrance, a heated pool, and a fully fenced backyard—ideal for families and added privacy. We’re pet-friendly too! Comfortable, central, and close to everything—perfect for your Sarasota getaway VR24-00164

ValueLocationKitchen

The spacious living area features a comfortable couch adorned with patterned pillows, a wooden coffee table, and colorful rugs. Natural light floods in through large windows, and an open layout connects to the dining area and kitchen, which is visible in the background.

4.98 out of 5 average rating, 132 reviews

Sunshine House, near Downtown, Legacy Trail, Beach

Great location! This is a family friendly home, close to downtown and beaches, with a pool, fenced yard, and a large, screened porch for lounging and having meals outside. Close to all the great things Sarasota has to offer- museums, gardens, theaters, shopping, Sarasota Bay, and beaches. The house is 1.5 miles from downtown, 10 min to St. Armands, 15 min to Lido Beach, and about 20 min Siesta Key Beach. One dog considered with a fee. Children must be supervised at all times in the pool area.

ValueFamilyQuiet

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 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.

4.84 out of 5 average rating, 219 reviews

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

Welcome to The Flamingo House! Settle in and enjoy the 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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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, 128 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!

LocationFamilyAccuracy

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, 149 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!

LocationValueSleep quality

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, 185 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.

ValueLocationGrill

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, 101 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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An outdoor dining area features a large table set with plates and glasses, surrounded by seating. A pool is visible nearby, framed by lounge chairs under a covered patio with ceiling fans. The walls are painted in a vibrant blue, enhancing the inviting atmosphere.

4.91 out of 5 average rating, 202 reviews

Sarasota Sandpiper: 4 Bed/3 bath + Pool

Your Ideal Getaway: All-Inclusive Comfort and Convenience Discover the perfect retreat that's close to everything you desire in a vacation. Whether you're seeking the beach, family-friendly activities, nightlife, mini golf or championship golf courses, you'll find it all at your doorstep. It's a place where you can unwind and savor life's simple pleasures. Embrace the great outdoors with an outdoor space that's perfect for relaxation and enjoyment.

LocationFamilyIndoor spaces

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, 106 reviews

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

Experience luxury at this newly remodeled home with a brand-new pool, spa, and putting green. Centrally-located near downtown Sarasota, Siesta Key, Lido Key beaches, and St. Armand’s Circle, it features a full kitchen, 3 king bedrooms, 3 full bathrooms, outdoor dining, high speed internet, a 75” outdoor TV, fire pit, and EV charger. Pet-friendly with a fenced yard, pet crate, bowls & treats. License # VR24-00208

FamilyLocationWalkability

The outdoor area features a heated pool surrounded by lounge chairs, providing ample space for relaxation. A dining set is positioned nearby, accompanied by an umbrella for shade. Lush greenery and palm trees border the property, complementing the serene atmosphere.

4.91 out of 5 average rating, 120 reviews

Rhodes Retreat - Beautiful Pool and Backyard Space

Bright and newly renovated home for a delightful family escape in Sarasota. Central location near beaches, shopping, and downtown, yet nestled in a serene neighborhood. Short walk to charming Amish Village of Pinecraft. Ample parking, garage, and spacious front yard. Option to book separate secondary unit. Siesta Beach 8.7mi, Lido 5.8mi. VR24-00264

FamilyLocationBeach

The modern kitchen features a large island with a marble countertop, topped with an arrangement of fresh fruits and drinks. A light fixture adds a soft glow above the island, while a cozy seating area with a dark sofa and brick wall can be seen in the background.

4.85 out of 5 average rating, 131 reviews

Sarasota Getaway “Have some fun under the sun.”

Bring the whole family to this newly renovated 4 bedroom house, with lots of room for fun. Heated pool available from November up to the start of April. Please keep in mind that the nights are cold during the winter months, and water gets cooler at night.

LocationFamilySleep quality

Popular amenities for Fruitville rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Gulf Gate Estates

4.89 out of 5 average rating, 107 reviews

Beachy Cottage close to Siesta | 3 Bed | Huge Pool

LocationFamilyDecor

A bright pink flamingo float adorns the clear, inviting waters of the heated pool. Two white umbrellas provide shade for the striped lounge chairs nearby. Flower pots add a touch of greenery to the poolside area, which is enclosed by a white privacy fence.

4.95 out of 5 average rating, 139 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

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4.83 out of 5 average rating, 41 reviews

Quiet Family Home w/ Pool Near Pinecraft

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5.0 out of 5 average rating, 39 reviews

Fun on Day Lane w/ Heated Pool

LocationFamilyBeach

4.95 out of 5 average rating, 22 reviews

Heated Pool and Spa Near Siesta Key

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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

LocationFamilyGetting around

A spacious backyard area features a mini-golf course marked by small flags, inviting relaxation and play. Comfortable hanging chairs are under a stylish pergola, while a fun play structure is visible, enhancing the outdoor space designed for family-friendly enjoyment.

5.0 out of 5 average rating, 48 reviews

Private Oasis: Mini Golf and firepit. 2 king beds.

FamilyValueOutdoor spaces

A spacious seating area features comfortable chairs surrounding a modern fire table. A clear view of the salt water heated pool is available through large glass doors. Outdoor furniture is positioned beside the pool, with lush greenery visible in the background.

5.0 out of 5 average rating, 57 reviews

Sunshine House- Sarasota Pool Retreat

FamilyValueQuiet

Condo rentals with a pool

Condo in Gulf Gate Estates

A cozy living area features a blue sectional sofa accompanied by decorative pillows and a side table with a lamp. A wall clock adds a modern touch, while large sliding glass doors offer views of the outdoor space. A dark blue accent chair complements the scene.

4.89 out of 5 average rating, 195 reviews

Lake View 1BR Condo | Heated Pool Near Siesta

ValueFamilyAmenities

4.92 out of 5 average rating, 169 reviews

Condo in Sarasota

Cottage on Siesta Key Beachside & Stunning sunsets

FamilyValueBiking

4.96 out of 5 average rating, 225 reviews

A serene lanai view features a dining table with chairs overlooking the community pool. Lush palm trees frame the scene, while sunlight reflects off the water's surface. A doorway is visible, leading to the interior of the condo.

Condo in Sarasota

Gateway to Siesta Key - 1/2 Mile to the Beach

FamilyValueBathroom

4.82 out of 5 average rating, 152 reviews

Condo in Lido Key

LIDO KEY 1 BR/1Bath Heated Pool 16

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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, 175 reviews

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

FamilyLocationOutdoor spaces

A dining area is presented with a large wooden table surrounded by blue upholstered chairs. Sunlight pours through expansive windows, revealing views of the turquoise waters and sandy beach beyond. A beach-inspired artwork decorates the wall, adding a touch of coastal charm.

5.0 out of 5 average rating, 103 reviews

Breathtaking Beachfront Views in Siesta Key

ValueLocationGetting around

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

FamilyValueBathroom

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

ValueFamilyLaundry

Other vacation rentals with a pool

4.97 out of 5 average rating, 73 reviews

A modern cottage is set within a spacious, manicured lawn surrounded by trees. A circular driveway leads to the house, which features a dark metal roof and large windows. Lush greenery frames the property, emphasizing its serene outdoor environment.

Cottage in Sarasota

Bee Keepers Cottage

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A private saltwater pool area is enclosed within a screened lanai, featuring two turquoise lounge chairs positioned beside a shallow seating area. Clear blue water glistens under a partly cloudy sky, while well-maintained green grass surrounds the pool enclosure.

4.99 out of 5 average rating, 78 reviews

Cheerful 3 bedroom home with heated salt pool.

FamilyLocationCheck-in

5.0 out of 5 average rating, 38 reviews

Belle of Sarasota

LocationFamilyPool

5.0 out of 5 average rating, 7 reviews

Sun Coast Oasis-Heated Pool-Pool Table-Arcade

FamilyLocationBathroom

4.98 out of 5 average rating, 65 reviews

Beautiful Oak View Manor - Siesta & Legacy Trail

LocationValueGrill

5.0 out of 5 average rating, 4 reviews

Kokomo Keys | Heated Pool + Outdoor fun park

FamilyLocationPool

4.89 out of 5 average rating, 61 reviews

Pet-Friendly Pool Oasis Near Siesta Key Beaches

FamilyLocationGetting around

An inviting outdoor area features a screened patio surrounding a heated pool. Comfortable seating is arranged under the enclosure, with lounge chairs and vibrant accents. Lush greenery is visible in the background, creating a serene atmosphere for relaxation and leisure.