Vacation rentals with a pool in Sarasota

4.92 out of 5 average rating, 385 reviews

Bungalow in Sarasota

Pool & fenced-in yard in downtown edge bungalow

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

A custom pool is framed by elegant lounge chairs and tropical landscaping. Water features create gentle curves, while illuminated details enhance the space as the sunset casts a warm glow. A covered outdoor area is visible in the background, providing seating and entertainment options.

4.97 out of 5 average rating, 105 reviews

Fruit /Botanical Garden Estate 2 ml to downtown EV

Indulge at this Mediterranean estate, boasting lush botanical gardens and rare tropical fruit trees for your picking pleasure. Enjoy the custom pool, hot tub, sauna, cold plunge and the home gym. The expansive outdoor haven features a fully-equipped kitchen, fireplace, TV, and dining space. Enjoy leisurely games of pool, ping pong & shuffleboard, then retreat to the luxurious indoors with comfortable beds and a massive TV, all within the privacy of a walled-in estate. Your lavish escape awaits.

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, 140 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

4.94 out of 5 average rating, 106 reviews

A Tiki bar with a thatched roof provides a stylish overlook of a heated pool surrounded by lounge chairs. The design features natural wood accents and vibrant decorations, inviting relaxation and leisure. Sunlight reflects off the water, adding to the serene outdoor atmosphere.

Home in South Sarasota

Tiki Bar Paradise! Heated Pool & Gaming Oasis!

Welcome to one of our beautiful properties, only 9 minutes to Siesta Key Beach! 24/7 Host Support - no AI messaging or hidden fees. Gorgeous HEATED POOL & Tiki Bar. Corn hole, ring game, or water pong on dry land or play volleyball, basketball, or beer pong in the pool. Bring the competition inside to the Game Room to play billiards or any number of family card/board games. Relax in the cozy living room w/ fireplace & fully equipped kitchen. Minutes to Siesta Key, the Village & Downtown SRQ.

4.96 out of 5 average rating, 186 reviews

The enclosed pool area is surrounded by lush greenery and tropical plants, with vibrant purple lighting creating a serene ambiance. A spacious swimming pool reflects the colors overhead, while a decorative wall clock adds a charming touch. Comfortable seating is present along the edges.

Apartment in Sarasota

ROYS PLACE Romantic, Private, Paradise!

NAMED #1 BEST AIRBNB WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE FOR THREE YEARS. "I LOVE ROYS PLACE!" Words most commonly used by guests in reviews are "quality" "clean" "cute" "sexy" "cool" "safe" . This is a restored 600 sq. ft. one bedroom apartment in an old historic home located in the heart of coveted safe Northwest Sarasota. Offered for you, a romantic boutique apartment with your own private (exclusive to you, not shared) CLOTHING OPTIONAL lanai, outdoor shower and heated pool.

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!

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.

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

4.92 out of 5 average rating, 172 reviews

Condo in Sarasota

Cottage on Siesta Key Beachside & Stunning sunsets

Come experience Siesta Key and relax in our beachside cottage. It is sure to refresh you , whether you prefer an incredible one of a kind sunset or a long leisurely walk on the beach with the cool sugar white sand beneath your toes! This is an escape you deserve. The pool is beautiful and conveniently located on your stroll to the beach. If you enjoy music , we are close to several places you can sit & enjoy under the Tiki Huts with refreshments!

4.99 out of 5 average rating, 160 reviews

A light blue bedroom features a spacious bed with a floral-patterned blanket and a ceiling fan overhead. Double glass doors provide a view of the pool area outside. Storage options include a white dresser and closet, while a small table and chair are positioned nearby.

Guesthouse in Sarasota

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!

4.98 out of 5 average rating, 130 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. 🌴

Apartment in Downtown Sarasota

Central Downtown Apartment with Pool and Gym

Stay in the heart of downtown in this stylish 2 bed, 2 bath apartment. Enjoy a bright open layout, fully equipped kitchen, cozy living area, and two comfortable bedrooms including a private primary suite. Building amenities include a sparkling pool with games and fully equipped gym. Walk to top restaurants, shops, and nightlife. Perfect for business trips or weekend getaways!

4.88 out of 5 average rating, 210 reviews

Popular amenities for Sarasota 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!

Superhost

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~

Superhost

An outdoor space showcases a heated saltwater pool with a calm blue hue, surrounded by comfortable lounge chairs. The area is framed by lush greenery and fencing, enhancing privacy. The backdrop features a gently lit sky at dusk, complementing the home's modern design.

4.95 out of 5 average rating, 110 reviews

Retreat by the Bay-Heated Saltwater Pool

4.98 out of 5 average rating, 133 reviews

Sunshine House, near Downtown, Legacy Trail, Beach

4.94 out of 5 average rating, 104 reviews

Home in South Bradenton

Stylish Pool Home • Near IMG & Beaches • Top Rated

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.

4.95 out of 5 average rating, 118 reviews

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

5.0 out of 5 average rating, 10 reviews

Sun Coast Oasis-Heated Pool-Pool Table-Arcade

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

Condo rentals with a pool

4.98 out of 5 average rating, 258 reviews

Condo in Longboat Key

Island Time: Open Columbus Day Weekend!

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, 105 reviews

Breathtaking Beachfront Views in Siesta Key

4.96 out of 5 average rating, 141 reviews

Siesta Key Condo. Checkout our great rates!

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

4.98 out of 5 average rating, 110 reviews

Condo in Longboat Key

Beach Condo with Quiet, Private Beach

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

Superhost

Condo in Lido Key

LIDO KEY 1 BR/1Bath Heated Pool 16

4.82 out of 5 average rating, 154 reviews

4.9 out of 5 average rating, 243 reviews

A screened lanai offers poolside views, with vibrant orange and blue chairs positioned to enjoy the scenery. Lush greenery borders the area, while palm trees sway in the gentle breeze. Glimpses of the Gulf of Mexico and a heated pool are visible through the railing.

Condo in Longboat Key

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Other vacation rentals with a pool

4.85 out of 5 average rating, 320 reviews

A secluded backyard features a heated pool surrounded by lush greenery and flowering plants. Tropical palm trees and colorful potted plants enhance the tranquil atmosphere, while the tiled pool edge adds a touch of contemporary design.

Bungalow in Sarasota

Private Siesta Beach House Oasis with Heated Pool.

4.98 out of 5 average rating, 104 reviews

A cozy living area features a light blue wall, with a comfortable white sofa arranged around a neutral-toned rug. In the foreground, a wooden dining table with four chairs provides seating. Natural light enters through a doorway that leads to an outdoor space.

Guesthouse in Bradenton

Serenity Lake

5.0 out of 5 average rating, 15 reviews

Home in Siesta Key

Steps to Siesta Key Beach! Sunset Balcony Views!

An inviting backyard showcases a pool surrounded by a concrete patio, featuring lounge chairs and a grill. Lush greenery and tropical palms create a serene environment. A shaded area with colorful seating offers a space for relaxation, enhancing the outdoor experience.

4.94 out of 5 average rating, 18 reviews

Tropical Oasis: Poolside Getaway

5.0 out of 5 average rating, 18 reviews

Good Vibrations Home

4.93 out of 5 average rating, 43 reviews

Home in Sarasota Springs

Quiet Family Home w/ Pool Near Pinecraft

5.0 out of 5 average rating, 8 reviews

Home in Englewood

Ibis Cottage | Beachfront Retreat on Manasota Key