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.

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Guest favorite

Home in Venice

4.91 out of 5 average rating, 46 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

Home in Sarasota

4.75 out of 5 average rating, 12 reviews

Serene House With Garden Heated And Spa

"Get away from it all" at this very special property that features huge private heated pool, spa and gardens. This home is a two story, spacious and newly renovated with all new furnishings. All bedrooms have high quality new mattresses. The house is equipped with high speed WiFi, board games, toys, playpen, highchair, baby stair gate, stroller, beach towels and chairs. This property will give you the privacy, but still keep you in close proximity of the beach, shopping, restaurants and movies.

Guest favorite

Home in West Bradenton

4.99 out of 5 average rating, 139 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 3 bedroom 2 bath pool home has an additional queen futon & queen sleeper sofa. 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 could easily serve as a 4th bedroom. Come & relax!

Superhost

Home in North Port

4.93 out of 5 average rating, 28 reviews

Cozy getaway home with Heated Pool!

Fall in love with this cozy vacation Home! Just minutes walk away from Florida's only warm mineral Springs. This freshly renovated home has 3 bedrooms, 2 bathrooms, open layout kitchen dining and living room. The pool is heated and enclosed in the lanai so you don't have to worry about any bugs. There are numerous beaches within 15-30 minute drive. There are multiple golf courses around, aqua park, beautiful parks and many more to enjoy. Many stores, restaurants are located just minutes away.

Guest favorite

Home in Palmetto

4.98 out of 5 average rating, 42 reviews

Charming Home Near Anna Maria Beach|Pool +Games

Discover some of the best beaches in the state when you stay at Casa Bonita! This beautiful, modern four-bedroom home is the perfect place for a large family or group of friends seeking peaceful enjoyment. Relax on the spacious deck, splash in the private pool, gather around the fire Pit or enjoy a variety of board games. 6 Min Drive to North River Body Therapies 20 Min Drive to Robinson Nature Preserve 22 Min Drive to St Pete & Anna Maria Beach Experience Palmetto With us & Learn More Below

Guest favorite

Home in Sarasota

4.98 out of 5 average rating, 133 reviews

Heated Pool Oasis 3BR/2BA near Siesta Key Beach

This Modern House with a heated pool near Siesta Key will be your home away from home! Renovated house has plenty of privacy, space and a lot of sunlight. Luxurious sleeping arrangements will guarantee a relaxing sleep. A quiet neighborhood with a lot of privacy and convenient proximity to all main attractions. A very spacious outdoor space at the pool will be your favorite spot for family dinners and entertainment. This house is located just 15 mins from the famous Siesta Key Beach.

Guest favorite

Home in Venice

4.91 out of 5 average rating, 178 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

Home in Venice

4.93 out of 5 average rating, 115 reviews

Great shape after Milton -Gorgeous Pool! - os

Great news! We've quickly reopened after Milton! Restaurants, stores, our beach access & Historic downtown-all now open! Beautifully decorated 3 bedrooms, 2 bathrooms, attractive family room & open concept kitchen with breakfast room overlooking private pool. On desirable Island of Venice, “Villa Sorrento” is only 8 minute walk to beach. Near Historic Venice Avenue's unique shops, restaurants. Low-key quiet vacationers only. 2 car max. no visitor parking. No pets. No smoking

Superhost

Home in Bradenton

5 out of 5 average rating, 3 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

Home in Nokomis

4.95 out of 5 average rating, 20 reviews

Beautiful Waterfront House, Pool, 7 Min to Beach

Have fun and make some great memories at this stunning 3 bedroom/ 2 bathroom pool house. Head outdoors and take a dip in the fully-screened pool, spend time grilling and dining on the pool deck, and enjoy your morning coffee while listening to the birds that frequent the lake and sanctuary island located behind the house. Only 7 minutes away from Nokomis beach.

Guest favorite

Home in Bradenton Beach

4.78 out of 5 average rating, 40 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.

Superhost

Home in Bradenton

4.88 out of 5 average rating, 122 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.