Basking in the Gulf of Mexico, just off the Sarasota coast, Siesta Key is a magical city in Florida that’s famed for its spectacular sunsets and pristine beaches. Adventure lovers and beach aficionados from all over the world come here to indulge in a thrilling beach adventure. Whether you are traveling alone or with a special someone, some of the beaches you might want to check out include Siesta Key Beach, Crescent Beach, and Sarasota Beach. You can enjoy blissful sunsets while strolling along the palm-lined Beach Road. There is also no need to worry about where to stay because this place has various options for you. To help you plan a fun getaway, read on this list of the top Airbnbs with pool in Siesta Key, Florida.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to pool. The image galleries get refreshed with the latest updates regularly. They were last updated on October 25, 2025.
1. Awesome family-friendly abode (from USD 6411)
The private saltwater pool inside the two-story lanai offers a refreshing getaway from the scorching weather. The property has a poolside grill with a propane tank where guests may prepare a delicious barbecue meal.
A 42-inch HDTV with access to primary streaming services such as Amazon Prime Video, Netflix, and Roku is available to guests. A crib, high chair, children’s dinnerware, and baby safety gates are also available. Recommendations for babysitters are also provided for people who require a little additional assistance.
Beach chairs and an umbrella are offered for guests to have fun at the nearby beach. Bicycles and helmets are also available, making exploration of the surrounding area simple and enjoyable. The backyard also includes a firepit, ideal for a lovely evening under the stars. Guests can park up to two automobiles in the garage, ensuring their vehicles are safe and secure.
Siesta Key, Florida, United States
3.03 km (1.9 mi) from Siesta Key WatersportsAccommodates: 6
Top guest reviews
Host:
liz was a great host and answered any questions promptlyelizabeth was a great hostelizabeth is a fabulous hostliz is a great host and the place is perfectelizabeth was a great host very responsive to any of our needs during our stayLocation:
a short walk or bike to the beach and siesta key is wonderfulgreat place in a quiet beautiful neighborhoodCleanliness:
it was spacious and cleanRead more reviewsAmenities & Room:
the pool was a ton of fun for the entire familythe bedrooms were great with plenty of room for our family of 5we used the pool daily and the lanai was great
2. Homey property with a hot tub (from USD 1893)
This homey property has a private outdoor pool, available all year round, heated for comfort. The pool boasts a perfect size, measuring 15 feet (4.57 meters) by 30 feet (9.14 meters), providing ample space for swimming and relaxation. Additionally, it is well-equipped with an array of pool toys to ensure all guests are entertained.
Including three cable TVs, guests can always find something to watch. Additionally, the home offers complimentary Wi-Fi and a designated workspace for guests who require a productive environment during their stay. Indulge in the ultimate relaxation experience with the availability of a private hot tub, ideal for unwinding and soaking away the stresses of daily routine. Moreover, the attached garage with a capacity of two cars guarantees the safety and protection of your vehicles.
Siesta Key, Florida, United States
3.91 km (2.5 mi) from Siesta Key WatersportsSuperhost
Accommodates: 4
Top guest reviews
Host:
marla was communicative and responsive prior to and during our tripLocation:
the neighborhood is nice to walk aroundgreat location for a more laid back siesta key vacationquiet and just beautifulCleanliness:
well equipped great location and very clean and spaciousRead more reviewsAmenities & Room:
the room off the master offers the perfect place for morning coffee on cool morningsthe house had everything we needed for a comfortable staythe pool area is beautiful
3. Spacious beach condo with bikes (from USD 229)
Book this spacious studio, which can comfortably accommodate three guests, for that resort-like feel without splurging. You’ll have access to a shared swimming pool. The studio comes with high-speed Wi-Fi and a laptop-friendly workspace, making it easy to work from home. There is a pack-n-play for guests with children. You’ll be supplied with bathing essentials, laundry facilities, extra pillows, and blankets for your convenience.
Treat your loved ones to a weekend barbeque using the community barbeque facilities. Since it is a beachfront condo rental in Siesta Key, you can rent cruiser bikes to explore the beach easily.
Siesta Key, Florida, United States
2.1 km (1.4 mi) from Siesta Key WatersportsAccommodates: 3
Top guest reviews
Host:
jayme is a great hostshe was extremely responsive to all questions i hadjayme was awesome she was great at communicating and very accommodatingjayme is definitely a super hostjayme was extremely responsive when i had questions and the room was very cleanLocation:
great location close to the village and beachnice stay and great location with a close walk to the veachthe location is within a 30 minute drive to the airport and numerous attractions in sarasotathe location to the beach and accommodations to the village was perfectamazing location and cute little studio by the beachRead more reviewsCleanliness:
stylish clean and fun little studiothe place was very clean and as describedthe unit is small but nice and cleanbathroom was clean and the water pressure pretty goodthe property was very clean
4. Magnificent beach home for family getaways (from USD 2339)
If your family is full of beach aficionados, then you’re surely going to have a wonderful family getaway in this magnificent home. Equipped with four bedrooms and five beds, the home puts you steps away from Siesta Key Beach. In this rental, you’ll be provided with beach chairs, a parasol, a beach cart, bikes, buckets, and towels for a memorable adventure.
Those who wish to stay indoors can have fun swimming in the screen-enclosed pool or relaxing in the hot tub sipping some wine.
Siesta Key, Florida, United States
3.89 km (2.5 mi) from Siesta Key WatersportsAccommodates: 7
Top guest reviews
Host:
kim is a great hostkim was very responsive with any questions we hadthe host was great and was there to answer any questions what may have hadwhat a kind understanding host i would definitely stay at her home againkim and raoul are very responsive and follow up on all communicationsLocation:
the location is perfectbeautiful house and great location close to everythinggreat place to social distance vacationclose to beach and village loved the poolgood location to get to the beach and village easilyCleanliness:
the house was very clean and the location was greatRead more reviewsAmenities & Room:
this floor is perfect for cooking great conversations or just watching the kids dip in the adjacent pool
5. Honeymoon Suite (from USD 431)
Bring your better half to this dazzling townhouse located mere steps from the beach for an exciting romantic escape. The property comes with two balconies where you can wind up your days admiring the romantic sunsets and picturesque garden views.
You can share intimate moments with your significant other at the black-bottom lagoon-style pool while sipping some wine. You’ll be offered pool and beach toys along with beach chairs and sun umbrellas.
Siesta Key, Florida, United States
2.96 km (1.9 mi) from Siesta Key WatersportsAccommodates: 4
Top guest reviews
Host:
owners were quick to respond with any questions and happy to provide recommendationshost was very responsive and informativevirginia was a great host and incredibly quick to respond to any questions we hadvirginia and vanessa are always a phone call away and very helpful with our questions and also recommendationsgreat communication and quick response from the hostLocation:
great location just steps away from siesta beacheasy walk to beach and villagebeautiful place great location close to everythinggreat location and loved the poollocation was perfect with just a short walk to the beach and quick drive to siesta key villageCleanliness:
the place was very clean and homeythe unit was extremely clean and well keptvery clean and everything was like the pictureslovely clean unit with nice locationit feels new and nice and clean and with stylish decorRead more reviewsAmenities & Room:
the suite is quite comfortable with all the amenities you needsweet heated shared pooleach of the units windows has a nice vantage point of either the pool or oceanvery comfortable king sized bed as well
6. Artsy abode close to the beach (from USD 2996)
This beautiful home in Siesta Key Village might tempt you to extend your stay, as it offers luxury amenities. What’s more, you can bring your four-legged companion with you because the property is one of the best pet-friendly accommodations. After having fun on the nearby beach, you can wash off the beach sand and relax in the private pool with a hot tub.
You can unwind on one of the sun loungers by the pool with a novel. There’s a spot where you can park your car on the property, for free.
Siesta Key, Florida, United States
3.55 km (2.3 mi) from Siesta Key WatersportsAccommodates: 4
Top guest reviews
Host:
gary was a wonderful host and very responsivegary went above and beyond as a host and truly cares that you enjoy your time while visitingthis house is amazing gary is the best host he is always ready to respond any questiongary the owner couldn’t have been more responsivesiesta key fantastic place to stayhost - very helpful and responsiveLocation:
i recommend this house and location to anyone wanting a break fromwe had a great week at this beautiful house close to siesta key villageprivate quiet and relaxing this place has it all great sunsets eateries and shopping all within walking distanceCleanliness:
the entire house was showroom cleanthe house is clean and has a great locationthe coolest house indeed the house is sparkling clean and comfy and the location is wonderfulRead more reviewsAmenities & Room:
we enjoyed the lovely furnishings fully equipped kitchen awesome pool in the backyard with spawonderful pool/deck space with a perfect combo of sun/shadefantastic back yard with pool/hot tub that ended almost every day with a smilethe house’s decor and vibe are a paean to all things midcentury and comfortable to bootthe backyard and pool area is so relaxing and tranquil
7. Beautiful apartment with pool table (from USD 1039)
Indulge in a thrilling beach adventure when you stay in this gorgeous condo that’s ideal for couples and solo adventurers. You can make the beach your playground thanks to the beach chairs, umbrellas, a rolling cooler, and a big beach bag provided by the host.
You can enjoy a picnic or a barbeque on the shores as you admire the dolphins. While indoors, you can pass time playing billiards. You can also have fun swimming in the heated outdoor pool.
Siesta Key, Florida, United States
909 meters (0.6 ft) from Siesta Key WatersportsAccommodates: 2
Top guest reviews
Host:
hosts are cery helpfuldebbie is a great host and very responsivedebbie is an excellent hostdebbie was a wonderful hostess she was communicative and friendlydebbie is definitely a super hostLocation:
location is the besta very comfortable and well locatedgreat location for a little getaway for this tampa localgood location close to beaches and just a short drive or trolley ride to village shops and restaurantsthe price was great and the location was super close to everything we needed and wantedCleanliness:
very clean and comfortable condothe condo was very clean and spaciousit was very clean we would come backgreat locations place very clean and quietclean condo and everything you need is right thereRead more reviewsAmenities & Room:
fully equiped kitchen a balcony a walking closet a perfect size bathroom location is perfectlovely stay at debbie’s condo good sized rooms and a huge closet perfect for a couplethe pool was heated and a great spot to cool offthe bed was very comfortable and had extra pillows and blankets
8. Cozy condo with a balcony (from USD 1336)
Set in a peaceful neighborhood a few steps from the beach, this cozy condo welcomes a maximum of four guests. It comes with two bedrooms furnished with queen beds for a great night’s rest. Spend your free time watching your favorite movies on the standard cable TV.
You can snuggle up on the balcony and admire the picturesque sunsets. When the summer temperatures start soaring, you can cool off in the outdoor swimming pool.
Sarasota, Florida, United States
804 meters (0.5 ft) from Siesta Key WatersportsAccommodates: 4
Top guest reviews
Host:
the host were very responsive and politethe hosts are very responsive and get back to you in a timely manneran amazing place hosted by amazing people had a beautiful stay and will definitely be backmelissa and brandon were exceptional hosts and were super quick on every communicationLocation:
the location is nicely located between both siesta key village and turtle beachthe location was perfectterrific location terrific value for the moneyperfect place to stay if you want to be close to everythingit is located in a quiet and beautiful placeCleanliness:
clean and cutevery clean with everything you needthe pool was very nice and clean as wellthe apartment itself is clean and highly organizedRead more reviewsAmenities & Room:
we enjoyed the heated pool at bay oaks and the meet and great evenings by the dockthe pool and clubhouse were wonderful amenities and the residence itself was cozythe king bed was firm but comfortable and there were plenty of pillows
9. Spectacular apartment with a hot tub (from USD 715)
You and your loved ones can be assured of a splendid stay in this colorful condo, one of the luxury rental properties in Siesta Key, that is found in Palm Bay Club Resort. The condo can host up to four guests, and it offers two bedrooms: one with a king bed and the other with two single beds.
Soak up the gorgeous bay vistas while enjoying refreshing laps in the pool. The pool area is fenced and equipped with sun loungers for relaxing. You can also take a refreshing dip in the hot tub next to the pool.
Siesta Key, Florida, United States
1.42 km (0.9 mi) from Siesta Key WatersportsAccommodates: 4
Top guest reviews
Host:
vickie and abe were excellent hostsabe is a great hosti highly recommend this host and accommodationsabe and vickie are perfect hostswe were pleasantly surprised how easy it was and accommodating the hosts wereLocation:
the location is fantasticgreat location a shot walk to the beachthe location is absolutely perfecta short walk to beautiful siesta key beach and close to bayside poolthe condo is a great location with walking distance to the beach and access to the trolleyCleanliness:
super clean and comfortablean incredibly spotless and lovely condothe condo was very clean and comfortablethe condo is very clean and the beds comfortablethe condo was clean and very well maintainedRead more reviewsAmenities & Room:
the pools were very nice and well maintainedwe were greeted with baskets of goodies and fresh fruit fresh flowers on the tableshe also had beautiful fresh flowers on the tablethis was a great condo with many amenities - pool hot tub fishing dock easy beach accessit was nice to have a well stocked kitchen to make some of our meals
10. Fabulous tropical condo with a private marina (from USD 3938)
If you’re visiting Siesta Key with your family, this spectacular tropical condo can be a great home away from home. It has two bedrooms, two bathrooms, and can comfortably accommodate five people. For outdoor relaxation, you can take a refreshing dip in either of the two pools or get a tan while relaxing on the sun loungers by the poolside.
Enjoy a game of tennis at the Har-Tru courts or work out in the modern gym facility. You can also play pool in the social room.
Siesta Key, Florida, United States
1.54 km (1.0 mi) from Siesta Key WatersportsAccommodates: 5
Top guest reviews
Host:
very responsive host who attended to our needs during our visitthe owners are super responsive and get right back to you immediatelycassidy & graeme are attentive and responsive hosts the condo is exactly as it appears in the picturesLocation:
close to the beach and very safelocation was perfect felt like a true florida beach staygreat location they are satisfied and would rebook in the future:)Cleanliness:
it is clean bright and well laid outcondo is very clean stylish and have all kitchen suppliesvery clean unit lots of linens and well appointed kitchensuper clean condo with gorgeous view of the oceanthis apartment has everything you need and was very clean on arrivalRead more reviewsAmenities & Room:
the bedding is new and the mattresses are very comfortablespacious with a nice kitchen and amenitiestwo bedroom with comfortable beds extra blankets and etcthe apartment has a wonderful view of the oceanlots of amenities in the building (pool tennis court gym an awesome marina where we saw dolphins)
11. Charming studio with partial beach views (from USD 150)
Escape the chaotic city streets and bring your better half to this charming studio that offers partial views of Siesta Key Beach. Perfect for two travelers, the studio comes with a comfy queen bed and a private bathroom stocked with necessary bathing essentials.
You can enjoy al fresco dining on the deck while admiring the stunning tropical scenery. Feeling tired and worn out? Wash off your stress in the outdoor swimming pool. You can also unwind in the bathtub.
Siesta Key, Florida, United States
4.07 km (2.6 mi) from Siesta Key WatersportsAccommodates: 2
Top guest reviews
Host:
she was also responsive when i had questionsmichelle was very responsive and extremely helpful during checkoutreally enjoyed our stay also great communication from our hostmichelle is an exceptional host - very responsive and answered all of our questionsLocation:
cute space ideal location and quick to respondthe location was perfectgreat spot perfect location near the beach and an easy 2 minute walk to popular restaurants and shoppinggreat place this is a cute property with a great locationtremendous stay again best locationCleanliness:
the place was very clean and well keptthe studio was very clean well equipped and tastefully decoratedplace is clean and perfect to walk to the beach or ocean aveour stay was amazing the place was spotless when we arrivedthe place was clean and had a very nice new pool (we did not use but looked inviting)Read more reviewsAmenities & Room:
and the new updated pool was fantastic
12. Stylish beach apartment with tennis courts (from USD 1547)
Enjoy magical sunsets and plenty of beach fun when you stay in this stylish apartment located on Siesta Key Beach. With two bedrooms and two bathrooms, this oceanfront Airbnb in Florida can comfortably accommodate a family of six.
There are three tennis courts and two pickleball courts for family fun. You can spend your afternoons wading in the stunning pool set next to the ocean. The pool is usually heated during the cold months and is fenced and equipped with sun loungers.
Siesta Key, Florida, United States
1.62 km (1.1 mi) from Siesta Key WatersportsAccommodates: 5
Top guest reviews
Host:
diego was a great host easy to communicate with and explained everything clearlyfully stocked and our host diego went above and beyond to make sure we had everything we neededdiego is a great hostdiego is a fantastic host checking in daily and providing so much information and tipsdiego is a super hostLocation:
the location is perfect - quiet and private but minutes from everythingdiego’s place is a comfortable stay in a prime location on the beach and easy access to other locationsthe location is great (it doesn’t get better )it was a little bit of a walk to the beach/pool but not too badwonderful place to stay will definitely come again :)Cleanliness:
the rooms were clean and the apartment is quite stylishthe place was very clean and perfect it was everything i could’ve imaginedthe apartment was clean modern and comfortable which created a perfect space to relaxexcelente stay at diego’s apartment the property was very clean comfortable and full equippedapartment was spacicious clean close to beachRead more reviewsAmenities & Room:
the resort provides free beach chairs which is so convenient the wifi was super fastthe wifi was great which was a plus because we worked half of our stayand umbrella rental was cheap and easy (even though there was an umbrella in the room
A once-in-a-lifetime vacation in Siesta Key
Siesta Key is a splendid destination on the Gulf of Mexico that has plenty of hidden gems waiting to be explored. In addition to the gorgeous beaches, the city boasts plenty of accommodations with pools. Book one of the above Airbnb vacation rentals with a pool and enjoy a once-in-a-lifetime holiday in Siesta Key.
Frequently asked questions about the top Airbnbs with pool in Siesta Key, Florida
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