Vacation rentals with a pool in Siesta Key

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Siesta Key

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

0 of 0 items showing

1 of 3 pages

Top guest favorite

A spacious backyard pool area features a heated pool surrounded by a secure screen enclosure. The inviting poolside is complemented by a paved patio and access to the home through sliding glass doors, revealing views of tropical landscaping and ample outdoor seating.

Home in West Bradenton

4.99 out of 5 average rating, 152 reviews

Suncoast Beach Getaway - 10 Minutes to Gulf & IMG

Enjoy some of Florida's finest white sandy beaches. Only 4 miles/10 minutes to the shimmering Gulf of Mexico or IMG Academy. This Luxurious 4 bedroom 2 bath pool home has an additional queen futon & 2 sets of bunkbeds. 100% remodeled by builder/owner. Over 2300 square ft. of A/C space (3 zones) all on one level with a huge private HEATED POOL. Featuring a fully stocked gourmet chef kitchen & stunning granite counters! The very large rear lanai also may also serve as a 4th bedroom. Come & relax!

Guest favorite

The screened-in pool area features a private swimming pool with a gently curving shape. Sunlight casts reflections on the water, while a colorful inflatable float rests nearby. Two white chairs and a small table are positioned to provide a relaxing space by the pool.

Home in Venice

4.91 out of 5 average rating, 57 reviews

Heated POOL close to beach fenced in, kid friendly

Family friendly, Pool home has an open floor plan. New kitchen w/ stainless appliances & a breakfast bar. Living room has sleeper sofa w/ upgraded memory foam mattress. Large sunroom overlooks the fully screened in private pool & fenced tropical backyard. Many amenities: washer & dryer, pool floats, beach chairs, umbrella, beach towels & toys, coolers. 7 min by car to Manasota beach, 5 min to shopping restaurants etc. Primary has ensuite bathroom, walk in closet. Pack n play crib, toys & games!

Superhost

A heated swimming pool is featured within a screened enclosure, surrounded by a blue patio. Beyond the pool, a serene view of lush greenery and a canal is visible, offering a sense of privacy and nature.

Home in North Port

4.81 out of 5 average rating, 134 reviews

Luxury villa 4 bdr with a heated pool (14guests)

Rare to find a luxury villa with a swimmable heated pool at the upscale district of North Port near a golf course. Very spacious (14 guests), high ceiling. Two empty lots on both sides of the property and a canal on the back guarantee full privacy. 2 minutes to Walmart and Publix. 10 minutes to Warm Mineral Spring. Close to Water park, Wellen park, Manasota, Siesta and others beaches. Very close to highways. The home is 2230 sq. ft. of living space. Fully furnished with high-end furniture.

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, 141 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.

Guest favorite

A screened-in pool area is presented, featuring a heart-shaped heated swimming pool surrounded by a spacious deck. Lush greenery and palm trees are visible beyond the enclosure, providing a serene outdoor setting for relaxation.

Home in Venice

4.91 out of 5 average rating, 183 reviews

Vacation Rental with private swimming pool

Located in a desirable community of South Venice. Venice, Manasota, Nokomis and Sharky’s beaches are located only 5 miles away. The historic Venice Avenue of unique shops, restaurants, special events. Farmer market, tennis courts, and children fountain are close by. Newly renovated home and swimming pool in a quiet peaceful area in an ideal place for any season gateway.A great place for biking, running and walking. My place great for couples, solo adventurers or families with kids.

Guest favorite

A private heated pool is surrounded by a screened lanai, providing a bright and airy space. Comfortable seating options are positioned nearby, along with a few plants adding a natural touch. Sunlight filters through the screen, casting gentle shadows across the deck area.

Home in Port Charlotte

4.92 out of 5 average rating, 139 reviews

Heated Pool Vacation Getaway

This 3 bedroom, 2 bath house with private heated pool is located in a quiet neighborhood near everything that Southwest Florida has to offer. Minutes from restaurants and grocery stores, a couple of miles from the Port Charlotte Harbor and a short drive to some of the most beautiful beaches, you can truly have it all. Our house offers great wifi, a fully functional kitchen, updated furnishings and a heated pool. Self check-in and out guarantee complete privacy.

Guest favorite

A spacious pool area is enclosed by a screened-in structure, featuring a sparkling blue pool and a sun lounger. Lush greenery surrounds the space and a serene lake is visible beyond, framed by a colorful sunset sky.

Home in Bradenton

5 out of 5 average rating, 16 reviews

Lakefront Pool Home w/Resort Amenities Near Beach

Escape to this lakeside haven with a private heated pool, just minutes from the pristine beaches of Siesta Key, Anna Maria Island, Bradenton Beach & Lido Key. Relax in the serene setting or explore the nearby sandy shores. Whether you're looking for a peaceful retreat or coastal adventure, this stunning getaway has it all for an unforgettable stay! Perfect for families, friends, or couples seeking both tranquility and excitement. Book your slice of paradise today!

Guest favorite

The inviting pool area is illuminated by string lights, adding warmth to the setting. A cozy seating arrangement is visible on the deck, while vibrant lounge chairs are positioned nearby. The soft glow of the water reflects the evening atmosphere, enhancing the relaxing environment.

Home in Bradenton Beach

4.77 out of 5 average rating, 44 reviews

AMI Sunset Beach - Pool Side Retreat w/ Pool +Deck

AMI's Sunset Beach part of 7 miles of white sand beaches! • 200+ five-star ratings over all sites! • Pool views from inside home. • Decks with views of Beach + Gulf of Mexico + Pool. • Pool with sun shelf. • Paddleboard + Kayak + Firepit + Patio + Grill. • High-speed WiFi. • First floor of duplex "pool-side". • Central location next to Sunset Beach.

Guest favorite

Vacation home in Sarasota

5 out of 5 average rating, 15 reviews

Stunning Sarasota Estate with Beautiful Pool

Newly renovated and spacious 4 bedroom home on a private and quiet 1 acre of land in the heart of Sarasota. Minutes from local restaurants, golf courses and shopping. 15 minutes to the beautiful Lido beach and 10 minutes to Downtown and the Marina. Fully secured fenced in yard and one of a kind backyard with a heated pool.

Superhost

The screened swimming pool reflects bright blue water, creating a serene space. Lush greenery and a pond can be seen beyond a white picket fence, providing a calming backdrop. Light clouds are visible in the distance, enhancing the outdoor setting.

Home in Bradenton

4.88 out of 5 average rating, 125 reviews

Coastal Charm

Charming 3 bedroom, 2 bath home with room to explore. Beautiful swimming pool that overlooks pond and x-large patio to enjoy outdoor dining and relaxing. Coastal decor throughout to enjoy your tropical surroundings. Just 5 miles and easy passage to the beach this home makes for an affordable beach vacation.

Guest favorite

A screened-in outdoor area features a heated saltwater pool surrounded by a concrete deck. Comfortable seating is provided with wicker chairs and a table, complemented by vibrant blue cushions. Lush greenery is visible through the enclosure, enhancing the serene environment.

Home in Sarasota

4.85 out of 5 average rating, 59 reviews

SieSta Key is Open,Heated Pool, 5min to Siesta key

Less than 2 miles to SIESTA BEACH public access #12 NO PARTIES OR EVENTS ALLOWED This is a happy place! You will find peace and tranquility in the spacious friendly home. Close to shops, bars, restaurants and less than 5min drive from Siesta Key Beach, voted #1 BEST BEACH IN USA in 2017

Superhost

Home in Sarasota

4.9 out of 5 average rating, 10 reviews

Charming House / Great Location ~ with Heat Pool~

Bring the whole family to this great place with lots of room for fun. Enjoy THE beautiful and Private outdoor pool and weather, nice outdoor seating and peaceful, back patio. corner house you gonna have a good experience with your family vacation and a Great Location.