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Vacation rentals with a pool in Fruitville

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Fruitville

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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A covered outdoor dining area is featured, furnished with a round table and four cushioned chairs. The space is positioned adjacent to the private pool, surrounded by a screened enclosure that allows for natural light and a view of the pool.

Bungalow in Sarasota

4.91 out of 5 average rating, 359 reviews

Pool & fenced-in yard in downtown edge bungalow

This 2 bed-2 bath house is a homey Florida bungalow with wood floors and lots of natural light, located in a quiet neighborhood on the downtown core edge. Enjoy a spacious and private, fenced-in backyard with pool, covered grill and eating area. The home is minutes away from the Legacy Trail, the new Bay Park, Payne Park, dining, live music, bars, theatres, opera house, performance venues, comedy club, antiquing, kayak launches, tennis and basketball courts, farmer's market, shopping and more.

A private backyard is highlighted by a welcoming pool surrounded by well-maintained pavers. Two yellow lounge chairs are positioned nearby, and a vibrant patterned towel is draped over a lounger. The screened porch provides additional space for relaxation, with a fenced area visible in the background.

Home in Sarasota

4.97 out of 5 average rating, 120 reviews

Sunshine House, close to Downtown

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.

Top guest favorite

A large, heated pool is enclosed within a screened patio, with clear water inviting relaxation. The surrounding area is spacious, featuring concrete flooring and a view of well-maintained landscaping beyond the pool, offering privacy and tranquility.

Home in Sarasota

4.98 out of 5 average rating, 148 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.

A private pool area is surrounded by a screened enclosure, featuring turquoise water and a white pool deck. Comfortable seating arrangements are placed nearby, along with potted plants that enhance the serene environment. The space is well-lit by natural sunlight filtering through the enclosure.

Home in Sarasota

4.81 out of 5 average rating, 156 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.

Top guest favorite

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.

Home in Sarasota

4.94 out of 5 average rating, 101 reviews

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

Embrace the height of comfort and convenience at your home away from home! Step into this meticulously renovated pool home, where spaciousness and brightness create an atmosphere of sheer luxury. Tucked away on a serene street, it offers a serene setting while keeping you close to Sarasota's prime attractions. Experience the allure of Siesta Key Beach, the vibrant downtown ambiance, and the renowned Fresh Fish Waltz Market—all just moments away. Plus, enjoy easy access to I-75.

A clear blue swimming pool is surrounded by a brick patio, with lounge chairs positioned nearby. Lush palm trees and greenery are visible in the background, providing a serene atmosphere. The pool's inviting water reflects the bright blue sky above.

Condo in Sarasota

4.86 out of 5 average rating, 123 reviews

Anchor house +6 min. from Siesta Beach+heated pool

★ "Ground floor 1 bedroom 1 bathroom apartment" ★ "An incredible apartment and 6 star hospitality!" 🌴 Stylish Retreat Near Siesta Key Heated Pool! Welcome to your perfect Sarasota getaway! This 600 sq. ft. pet-friendly home offers a heated pool access, and a prime location just 6 minutes from Siesta Key Beach. Whether you're here for a beach vacation, a family trip, or a remote work retreat, this home has everything you need for a comfortable and stress-free stay.

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.

Home in Sarasota

4.93 out of 5 average rating, 174 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.

Top guest favorite

A serene pool area is captured, featuring a turquoise pool surrounded by a screened enclosure. Comfortable lounge chairs are positioned nearby, and a decorative statue is visible by the pool's edge. Lush greenery and a wooden fence enhance the tranquil setting.

Guesthouse in Sarasota

4.99 out of 5 average rating, 141 reviews

Maggie's Hideaway

This adorable little bungalow is hidden away in one of Downtown Sarasota's oldest historical neighborhoods and only a couple miles from Sarasota Bay and surrounding beaches. Beautiful Lido Beach is only five miles west, Siesta Key is seven miles southwest, with Benderson Park being only seven miles east. Fabulous shopping and world class dining is plentiful in this downtown community. There is plenty to see and do in Sarasota - Come see us!

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.

Home in Sarasota

4.92 out of 5 average rating, 107 reviews

Heated Pool 3bdr 2bth Close to Downtown

Freshly remodeled home as of 2021, Great for family vacation. Amazing location right in the middle of town, no more than a ten minute drive to the incredible attractions. Easy drive to the #1 beach/Siesta beach world famous for its astonishing clear waters and impeccable views. This home has a private entrance with a heated outdoor pool. We are also pet friendly/dog. Small dog only, under 15 pounds, pet fee required.

Apartment in Downtown Sarasota

4.88 out of 5 average rating, 162 reviews

Downtown Apartment w/ Pool, Gym, & Coworking 329

This 2/2 apartment features an oversized kitchen with island, slider with views of Downtown. Primary has a king bed and en-suite bathroom. 2nd bedroom has a twin bed with twin trundle. Shared amenities include: gym; sunset deck; massive roof deck with heated pool; gazebo with big-screen TV, fireplace, wet bar, dog run and access to the adjacent Cowork office space building. Also on-site is a full service cafe.

A freeform pool is framed by lush tropical landscaping, featuring multiple waterfalls that flow into the water. The elevated home overlooks the pool area, complemented by large windows and a wraparound balcony.

Island in Sarasota

4.97 out of 5 average rating, 332 reviews

NEW 4/NTS AUG OPEN! Sarasota #1 Lux BEACH Villa

BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

Top guest favorite

A relaxing outdoor space features a lounge chair adorned with a striped towel and a wide-brimmed hat. A tray holds a refreshing drink beside the crystal-clear pool, surrounded by lush tropical foliage and a colorful float visible in the water.

Villa in Sarasota

5 out of 5 average rating, 110 reviews

Tropical Luxury: Pool, Game Room, Near Beaches

Welcome to your luxury, pet-friendly retreat! Just 15 min to Siesta & Lido beaches and the airport, this 4-bed oasis packs resort vibes into one easy stay. Heated pool & covered game room Sun-filled lounge, fire-pit & fenced yard Plush luxury beds for dreamy sleep Chef-ready kitchen, washer & dryer Unwind, explore, repeat—your tropical getaway starts here.

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Popular amenities for Fruitville rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

A spacious living room is presented with neutral-toned sofas adorned with colorful cushions. A coffee table with decorative items is centered between the seating, while light enters through large windows framed by soft blue curtains. A decorative plant adds a touch of greenery.

Home in Sarasota

5 out of 5 average rating, 30 reviews

Great Rates! Sunny Sarasota Villa! W/ 2 bicycles!

Home in Sarasota

4.92 out of 5 average rating, 24 reviews

Coastal Calm - 3BD/2BA Heated Pool Near Beaches

An inviting outdoor space features a private in-ground saltwater pool, surrounded by green grass and lounge chairs. Tropical landscaping provides a serene backdrop, with various plants and trees enhancing the atmosphere. Two umbrellas and a shaded seating area facilitate relaxation and outdoor enjoyment.

Home in Sarasota

5 out of 5 average rating, 3 reviews

Artsy 3BR/2BA Pool Home Arlington Park

Top guest favorite

A spacious screened-in pool area features a bright blue pool alongside lounge chairs. Strings of lights illuminate the space as the sunset casts a warm glow. Lush greenery surrounds the area, providing a tranquil setting for relaxation and entertainment.

Home in Sarasota

5 out of 5 average rating, 11 reviews

Fenced Yard|Gourmet Kitchen|Salt Water Pool|Arcade

Top guest favorite

A private fenced yard features a large swimming pool surrounded by a patio. Two lounge chairs are positioned nearby on a sunlit deck. A covered porch is visible in the background, offering additional seating options. Lush greenery borders the space, enhancing relaxation.

Home in Sarasota

4.89 out of 5 average rating, 84 reviews

Gorgeous renovation with pool, minutes from beach

Top guest favorite

A newly constructed home is presented on a well-maintained lot, surrounded by lush greenery. Tropical palm trees are visible in the front yard, and a red car is parked in the driveway. The double garage features a clean, modern design.

Home in Sarasota

5 out of 5 average rating, 50 reviews

NEW Luxury! Townhome in Sarasota

A spacious lanai is featured, housing a solar-heated pool surrounded by a screened enclosure. Comfortable outdoor seating accompanies the pool area, providing a relaxing atmosphere, while lush greenery is visible through the screens, enhancing the serene outdoor experience.

Home in Sarasota

4.87 out of 5 average rating, 67 reviews

Huge private Patio with heated pool near beaches

A screened-in pool area features a tranquil body of water, surrounded by plants and illuminated pathways. Two blue pool loungers are positioned on the water's edge, inviting relaxation. A privacy fence is visible, providing a secluded atmosphere.

Home in Sarasota

4.83 out of 5 average rating, 6 reviews

Casa SRQ

Condo rentals with a pool

Top guest favorite

Condo in Siesta Key

4.97 out of 5 average rating, 331 reviews

On the Beach; Siesta Key SunBum Studio

A two-story building with a light yellow exterior is situated among palm trees and lush greenery. The entrance features a covered porch, and the pathway is lined with flowering plants, leading to the parking area and common spaces.

Condo in Lido Key

4.8 out of 5 average rating, 104 reviews

LIDO KEY 1 BR/1Bath Heated Pool 16

Top guest favorite

Condo in Bradenton

4.96 out of 5 average rating, 111 reviews

A&A's Paradise near IMG & Anna Maria beaches

A large heated pool is visible, surrounded by lounge chairs for relaxation. Tall palm trees frame the area, and the building's exterior provides a backdrop. The clear blue water reflects the sunny sky, inviting guests to enjoy a refreshing swim.

Condo in Sarasota

4.86 out of 5 average rating, 152 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

Top guest favorite

Condo in Bradenton

4.96 out of 5 average rating, 137 reviews

Cozy 2 bed/2.5 bath townhome

A large heated outdoor pool is surrounded by lounge chairs, offering ample space for relaxation. The pool area is framed by palm trees, with a view of the condominium building and parked cars in the background, creating a welcoming environment.

Condo in Siesta Key

4.94 out of 5 average rating, 113 reviews

Siesta Key Beach Front Condo

A charming studio space features a queen size bed with a white blanket and decorative pillows. A small nightstand sits beside the bed, and a light is positioned for reading. Natural light enters through a large window with blinds, complementing the wood-look flooring.

Condo in Lido Key

4.95 out of 5 average rating, 143 reviews

Lido-Key- Tiny Studio Holiday Cottage-A

A heated pool invites relaxation, surrounded by lush tropical landscaping. Two colorful umbrellas provide shade over patio tables and chairs, arranged for guests. Palm trees line the background, offering a serene atmosphere near the beachfront. The clear blue sky enhances the inviting setting.

Condo in Longboat Key

4.88 out of 5 average rating, 104 reviews

Beautiful Panoramic Gulf and Sunset Views.

Other vacation rentals with a pool

A heated swimming pool is enclosed within a screened patio, featuring a turquoise hue. Red lounge chairs and an umbrella are visible alongside the pool, providing a comfortable area for relaxation. The surrounding fencing offers privacy, while tropical plants add a natural touch.

Home in Sarasota

4.91 out of 5 average rating, 91 reviews

Sarasota Getaway “Have some fun under the sun.”

A screened-in pool area features a heated, saltwater pool surrounded by a spacious deck. Lounge chairs are positioned nearby, with an outdoor grill visible in the background. A shaded overhang provides a comfortable space, and the pool floats rest gently on the water's surface.

Home in Sarasota

4.91 out of 5 average rating, 99 reviews

The Black Swan- private heated pool

A serene pool area is enclosed by a screened structure, featuring a small circular spa at its center. Soft lighting enhances the space, and several benches are positioned around the pool. Potted plants add greenery, while the surrounding walls are painted in a subtle hue.

Guesthouse in Sarasota

4.94 out of 5 average rating, 96 reviews

Cabana/Guest house w/spa/pool 5min to Siesta key.

Top guest favorite

A private lanai features a saltwater pool surrounded by a screened enclosure. Comfortable seating areas are provided, alongside potted plants that enhance the serene atmosphere. A clear blue sky and leafy trees are visible in the background, contributing to the tranquil setting.

Home in Sarasota

5 out of 5 average rating, 11 reviews

PrivateTropical Oasis w/Salt Water Pool

Home in Sarasota

5 out of 5 average rating, 4 reviews

Prairieview Pool House

A vibrant pool is surrounded by a fenced yard, featuring greenery and decorative plants. Two lounge chairs are positioned near the pool, providing a space for relaxation. Sunlight filters through the leaves above, creating playful shadows on the water's surface.

Home in Indian Beach-Sapphire Shores

4.94 out of 5 average rating, 54 reviews

Beautiful Florida Bungalow

A crystal-clear pool is surrounded by a spacious deck, featuring several lounge chairs arranged for sunbathing. Lush palm trees stand nearby, and a tranquil water view of the golf course is visible in the background.

Condo in Sarasota

4.92 out of 5 average rating, 38 reviews

Water view condominium in a beautiful community

A modern kitchen features sleek cabinetry, stainless steel appliances, and a central island with seating. Light-colored countertops and wood grain flooring create a bright and inviting space. Natural light is provided by a window, while an open layout connects the kitchen to the living area.

Villa in Sarasota

4.83 out of 5 average rating, 53 reviews

Your own tropical paradise in Sarasota

Quick stats about vacation rentals with a pool in Fruitville

Total rentals
110 properties
Nightly prices starting at
ﺩ.ﺇ110 before taxes and fees
Total number of reviews
4K reviews
Family-friendly rentals
100 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace

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