Vacation rentals with a pool in Fruitville

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.

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.

Apartment in Indian Beach-Sapphire Shores

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.

4.96 out of 5 average rating, 175 reviews

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.

4.99 out of 5 average rating, 225 reviews

A private stock tank pool is surrounded by a wooden deck and lounge chairs. An umbrella provides shade over the pool area. Colorful towels and a stylish table with refreshments are visible, set amidst a landscaped courtyard with lush greenery.

Guesthouse in Whitfield

Magical Guesthouse 1 mi from SRQ airport

@Aloe_Stranger Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

Superhost

A private pool is surrounded by a paved area, featuring two lounge chairs positioned near the water. Green foliage adds a natural touch, while a white fence encloses the space, creating a secluded atmosphere. The clear blue water reflects the sky, inviting relaxation.

Cottage in Bellevue Terrace

4.92 out of 5 average rating, 131 reviews

Private Heated Pool Casita Near Downtown & Beaches

Built in 1925, Our Casaita Verde 2 Bedroom, 1 Bath home still retains its vintage charm but with modern touches. Enjoy watching the 55 inch flat screen TV with HD cable and stay in touch with the world with WI-FI internet. Lounge by the private pool or take in the beautiful evenings on the deck with your favorite beverage. Pet Friendly! Conveniently located near Downtown Sarasota on Bahia Vista with easy drive to Lido Key, our World Famous Siesta Key or I-75 for longer adventures.

4.94 out of 5 average rating, 125 reviews

Pool Courtyard, patio w/ fire pit, 2 mls downtown

Enjoy this unique courtyard-style Spanish colonial home just steps to Sarasota Bay and 2 miles from downtown. The property consists of a 2 bed / 1 bath main house AND a detached studio. Everything pictured is yours to enjoy, nothing is shared. The houses are separated by a quaint & private pool courtyard w/ outdoor shower. Capture a photo of the local peacocks, eat fresh mangos from the yard, catch a sunset over the bay, or enjoy the sun by the pool listening to the Zen fountains.

4.94 out of 5 average rating, 106 reviews

Luxury Heated Pool/ Family Home/Siesta Key/3BR/2BA

Welcome to your home away from home! This renovated, spacious and bright pool home will immerse you into 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 USA), 10 minutes to downtown including fantastic restaurants and shopping and walking distance to the famous Fresh Fish Waltz Market. Easy I-75 access, Nathan Benderson Recreational Lake park and The new UTC mall!

A screened-in private pool area is visible, featuring a spacious rectangular pool bordered by sun loungers. Lush greenery is seen beyond the pool, providing a serene backdrop. A shaded outdoor dining area is positioned nearby, contributing to the inviting outdoor space.

4.86 out of 5 average rating, 100 reviews

The Aqua House-3/2 w/ heated pool by Golf Course

Unwind in this chic, well-appointed home, perfect for a memorable family escape. With 3 bedrooms boasting plush comfort and 2 modern bathrooms, it offers ample space. The generously stocked kitchen invites culinary delights. Start your day in the screened pool area overlooking the golf course, sipping coffee, or bask in serenity with an evening cocktail while floating in the pool. Siesta Beach is 14 miles away and Lido Beach is 11 miles away. Your relaxing retreat awaits!

Superhost

A screened outdoor area features a shaped pool and a hot tub. Sun loungers sit along the edge, and a large umbrella provides shade over a seating area. The space is surrounded by greenery, contributing to a serene environment.

Guest suite in Sarasota

4.72 out of 5 average rating, 291 reviews

Prvt entry Suite-2nd Fl HotTub/pool & beach items

This location is * 8.6 * miles from Siesta Key Beach 18-22 min drive Entire upstairs private in-law suite sleeps (4) people (king bed & queen pullout couch) w/ bathroom, & kitchenette. We live on the property AND have a ADDITIONAL UNIT which is located directly below this room for rent. Shared areas for all guests are pool/hot tub, patio, and garage areas. The pool/hot tub operate within hours listed. The “stove” listed is a hot plate wi the three burners.

4.99 out of 5 average rating, 142 reviews

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

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!

Home in Gulf Gate Estates

A heated pool is framed by a screened enclosure, allowing for sunlit swims while providing shade. Comfortable lounge chairs are lined along the poolside, and greenery is visible in the background, creating a serene atmosphere for relaxation.

4.93 out of 5 average rating, 106 reviews

2BR/2BA home w/ heated pool, 5 min to Siesta Key!

Charming 2BR/2BA Lakefront Home with Heated Pool – Just 2 Miles to Siesta Key Beach! Escape to this picturesque lakefront retreat, only 2 miles from the world-famous Siesta Key Beach. Perfect for families or groups, this spacious and beautifully furnished home offers a relaxing and memorable getaway. Lounge by the heated pool, soak in stunning lake views, or explore nearby attractions—this home is your ideal Sarasota vacation base.

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.

4.89 out of 5 average rating, 100 reviews

The Black Swan- private heated pool

Escape to a stunning mid-century modern retreat with a private screened pool. This 3-bedroom, 2-bath home is thoughtfully designed as your home away from home. Enjoy family gatherings by the pool or unwind in the fully stocked kitchen and dining room. Conveniently located minutes from downtown, and just a short drive to Siesta Key (11mi) and Lido Beach (7.8mi). Your perfect blend of relaxation and accessibility awaits!