Holiday rentals with a pool in Fruitville

4.91 out of 5 average rating, 122 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.

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.

4.92 out of 5 average rating, 130 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

4.91 out of 5 average rating, 376 reviews

Bungalow in Sarasota

Pool & fenced-in yard in downtown edge bungalow

MESSAGE ME FOR DAYS YOU DONT C. This 2 bed-2 bath house is a homey Florida bungalow with wood floors & natural light in a quiet neighborhood on the downtown core edge. Spacious and private fenced-in backyard with pool, covered grill and eating area. Minutes away from the Legacy Trail, the Bay Park, Payne Park, dining, live music, bars, theatres, comedy, opera house, performance venues, comedy club, antiquing, kayak launches, tennis and basketball courts, farmer's market, shopping and more.

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.

4.97 out of 5 average rating, 117 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, 1 twin bed and 2 twin air mattress. 4 smart tvs. We love this stunning and cozy home and we’re sure you will too!

A distinctive triangular structure features large glass windows, showcasing vibrant lighting from within. The exterior is surrounded by landscaped greenery and decorative white stones, enhancing the inviting appearance. Palm trees and a tidy paved driveway contribute to the overall charm and unique architectural design.

4.95 out of 5 average rating, 240 reviews

Modern, Bright Downtown SRQ A-Frame West of Trail

Enjoy this bright, newly renovated unique pool home on a street with mostly waterfront homes featuring 4 beds & 3 baths, office area options, loft reading nook, Bosch appliances, bedroom skylights, artful light fixtures and fully fenced with heated pool. Central to & minutes from Siesta Key, St. Armand's Circle/Lido Key, downtown. Walk to the Sarasota Arts Museum, grocery, Southside and downtown Restaurants & shops, Selby Botanical Gardens, Bayfront Park, & Marina Jack. VR24-00157

4.98 out of 5 average rating, 110 reviews

Pool, Shuffleboard, EV charg, Near beach, UTC mall

Welcome to Vistalodgings Villa Del Sol where families have fun ☀ 3 bedrooms: 1 king, 1 queen, 1 full, 1 twin bed and 2 full bathrooms ☀ Fully equipped kitchen: Keurig dual coffee maker, waffle maker, air fryer, electric kettle, blender, mixer, pots and pans ☀ Dining area for 8 ☀ Fast speed internet Wi-Fi ☀ Heated pool free of charge ☀ EV charger ☀ Shuffleboard, Pac-man arcade ☀ 5 Smart TVs with Disney Plus ☀ Bikes, beach chairs, umbrellas, cooler, beach toys ☀ Iron

A modern house is presented with a neatly manicured lawn and a driveway leading to a garage. Lush palm trees and potted plants frame the entrance, while large windows allow natural light to fill the interior. The structure has a welcoming white facade under a gray roof.

4.96 out of 5 average rating, 104 reviews

Casa Cruz-3RM/2BA w/Heated Salt Water Pool

You'll have a great time at this modern 3RM/2 BA house with a heated salt water pool. This beautiful home is located 6 minutes to SRQ Airport, 20 minutes to the #1 rated beach in the country, Siesta Key, 5 minutes to Publix and local restaurants, and 10 minutes to high-end shopping at UTC mall. You’ll have access to major FL highways. The home is equipped with all the essentials needed for short term/long term stays. Book your stay today! Casa Cruz es su Casa!

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 out of 5 average rating, 52 reviews

Sunshine House- Sarasota Pool Retreat

Welcome to the Sunshine House a sunny Sarasota retreat! This charming 3-bedroom, 2-bathroom home features a salt water heated pool and is just 20 minutes from the stunning Lido and Siesta Key Beaches. Perfect for families or groups, our home offers a spacious living area, fully equipped kitchen, comfortable bedrooms and an office setup. Relax by the pool, enjoy nearby dining and shopping, or explore the beautiful beaches. Your perfect getaway awaits!

A person is seated at the edge of a sparkling pool, facing the clear blue water. The poolside is tiled, and the sunlight reflects off the surface, creating a serene ambiance. The individual wears a swimsuit featuring a tiger stripe pattern.

4.96 out of 5 average rating, 134 reviews

Luxury Pool Family Paradise-Siesta Beach-3BR/2BA

Prepare to be enchanted by your new sanctuary! Immerse yourself in luxury at this spacious and bright pool home, recently renovated to perfection. Located on a peaceful street, it strikes the perfect balance between tranquility and convenience, with easy access to Sarasota's finest attractions. Unwind at Siesta Key Beach, indulge in downtown's culinary delights and shopping, and explore the famous Fresh Fish Waltz Market—all just minutes away!

4.98 out of 5 average rating, 115 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴

4.98 out of 5 average rating, 360 reviews

A stunning pool area is surrounded by lush greenery and tropical plants. A prominent rock feature with multiple waterfalls is visible, providing a serene focal point in the outdoor space. The vibrant blue water complements the natural elements, creating a tranquil retreat.

Island in Sarasota

JULY AVAIL! Sarasota #1 Luxury Villa w/PRIV BEACH!

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!

A fenced saltwater pool area features a spacious pool surrounded by a tiled deck. Lounge chairs are positioned nearby, inviting relaxation. Lush greenery provides a natural backdrop, while a covered outdoor seating area is visible in the distance, creating an inviting outdoor space.

5 out of 5 average rating, 29 reviews

Fun on Day Lane w/ Heated Pool

Bring the whole family to this great place with lots of room for fun. The home has everything you need for a fun vacation. Our pool is a saltwater pool with a great lounge area leading out to the pool. There is also outside seating. We are 10 Minutes to downtown Sarasota. Beaches: - Siesta Key Beach, 11 miles - Lido Key/St Armand’s Circle, 7.7 miles

Popular amenities for Fruitville rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

An updated kitchen is showcased with white cabinetry and a large island. Stainless steel appliances, including a gas stove, are visible. Natural light enters through a sliding glass door that leads to the outdoor area with a view of the pool. Fresh flowers add a touch of color.

5 out of 5 average rating, 10 reviews

Oasis, 3 Bedroom, Pool

Superhost

A single-story home is framed by lush greenery and colorful foliage. The front yard features well-maintained grass and several mature trees. The house showcases a light-colored exterior with a blue garage door, and an arched window is visible, contributing to a welcoming appearance.

4.77 out of 5 average rating, 22 reviews

Poolside Paradise on Linwood

4.89 out of 5 average rating, 61 reviews

Pet-Friendly Pool Oasis Near Siesta Key Beaches

A private pool area is enclosed by a screened-in lanai, featuring clear blue water reflecting sunlight. A patio umbrella and several chairs are positioned nearby, surrounded by lush greenery, creating a relaxing outdoor space.

4.98 out of 5 average rating, 85 reviews

GARDEN VIEW HOUSE WITH A POOL

Superhost

5 out of 5 average rating, 3 reviews

Luxury 4B Home & Heated Pool, Resort for 10 guests

4.95 out of 5 average rating, 55 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

A living room area is furnished with a green sofa and two beige armchairs, complemented by a round ottoman. Light wood accents are featured, with a large area rug underfoot. Natural light filters through two windows, and a potted plant adds a touch of greenery.

5 out of 5 average rating, 32 reviews

Driftwood Cottage - 3 BR with Salt Water Pool

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.

4.9 out of 5 average rating, 10 reviews

Casa SRQ

Condo rentals with a pool

4.96 out of 5 average rating, 218 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

4.99 out of 5 average rating, 105 reviews

The balcony features a cozy seating arrangement comprising two chairs and a coffee table, all set against a stunning ocean view. The turquoise waters and sandy beach are visible beyond the railing, offering a serene backdrop for relaxation.

Condo in Siesta Key

6 Siesta Breakers - Condo, Ocean View, Heated Pool

4.83 out of 5 average rating, 142 reviews

Condo in Lido Key

LIDO KEY 1 BR/1Bath Heated Pool 16

4.86 out of 5 average rating, 106 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.

Condo in Siesta Key

Comfy Siesta Key Condo

4.84 out of 5 average rating, 163 reviews

A cozy living area is depicted, featuring a comfortable sofa and two light blue armchairs. A wooden coffee table is centered in the space, while a small TV is positioned on a decorative cabinet. Soft lighting from floor lamps enhances the inviting atmosphere.

Condo in Siesta Key

Siesta Key Ground Floor Condo 2BR On Trolley Line

Condo 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.

4.86 out of 5 average rating, 144 reviews

Heated Pool Apartment Near Siesta Key | 1BR

4.96 out of 5 average rating, 190 reviews

A light-filled living area showcases a large white sectional sofa adorned with colorful throw pillows. A turquoise coffee table displays decorative shells, and a light-toned area rug is centered beneath. Artwork featuring vibrant coastal scenes is mounted on the walls, enhancing the relaxed ambiance.

Condo in Bradenton

The Seabreeze Cottage with peaceful water views

4.98 out of 5 average rating, 239 reviews

Condo in Longboat Key

Island Time on LBK!

Other holiday rentals with a pool

5 out of 5 average rating, 9 reviews

A modern park model home is shown with a red convertible parked in front. Lush palm trees surround the property, providing shade. A spacious patio area with outdoor seating is visible, complementing the vibrant landscaping and inviting exterior.

Cottage in Sarasota

Sarasota Cottage Near Beaches, Downtown & Airport

5 out of 5 average rating, 19 reviews

Home in Saint Armands

Luxury Lido Key Getaway on St. Armands Circle

4.91 out of 5 average rating, 11 reviews

Modern Coastal | Heated Pool | Family-Friendly

4.98 out of 5 average rating, 51 reviews

Condo in Sarasota

Charming Poolhouse · 1BR · Close to Siesta

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.

4.89 out of 5 average rating, 93 reviews

Gorgeous renovation with pool, minutes from beach

A solar heated pool is enclosed within a screened lanai, featuring a unique shape and clear blue water. Two lounge chairs are situated nearby, and sunlight creates gentle reflections on the pool's surface. Lush greenery is visible beyond the fence, enhancing the tranquil setting.

4.98 out of 5 average rating, 54 reviews

Three bedroom pool home in Sarasota

A spacious heated pool is enclosed by a screen, surrounded by a large patio area. Sun loungers are positioned nearby, while a shaded seating area can be seen in the background. Lush greenery and trees provide a natural backdrop, creating a serene environment.

4.94 out of 5 average rating, 31 reviews

A Whale of a Good Time!