Vacation rentals with a pool in South Sarasota

Find and book unique homes with a pool on Airbnb

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Popular amenities for South Sarasota rentals with a pool

House rentals with a pool

Top guest favorite
Home in Sarasota
4.97 out of 5 average rating, 67 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

KyleRating, 5 stars1 week ago
A beautiful home with a private, relaxed atmosphere and all the amenities you could need.
Top guest favorite
Home in Sarasota
5 out of 5 average rating, 58 reviews

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

CharlieRating, 5 stars1 week ago
My wife and I had a great time at this stay. Lots to do at the house along with great beaches and restaurants within a 15-20 minute drive. The house was clean and had everything that you might need. We were able to drive to Disney in just over an hour and a half which provided a different experience to go along with the daily beach/pool trips. Cool AC inside to combat the humid 88 degree weather in June 2025.
Guest favorite
An outdoor dining area is presented next to a heated pool, featuring a table set with plates of food and drinks. A gas grill is nearby, and the pool is enclosed by a mesh screen. Lush greenery is visible through the enclosure, enhancing the serene environment.
Home in Sarasota
5 out of 5 average rating, 5 reviews

Paradise on Prospect w/ Htd Saltwater Pool

NatalieRating, 5 stars2 months ago
This is the nicest vacation rental. The details are spot on. It is well appointed with quality products. PMI Is very responsive. Love the location and proximity to Ed Smith, Downtown Sarasota and more. We look forward to returning.
Top guest favorite
Home in Sarasota
4.93 out of 5 average rating, 28 reviews

Waterfront Home w/King Studio & Pool, by Siesta

EmilyRating, 5 stars2 weeks ago
The home was perfect for our family. Plenty of space and the in law suite was amazing. Everything was very clean and well maintained. While our girls enjoyed the pool, our boy was casting his fishing pole from sun up to sun down. It is located in a very quiet peaceful neighborhood, yet close enough to the tourist areas to drive to them in 10-15 minutes. Amy is absolutely a 5- star host and if we’re ever in the area again, we will ABSOLUTELY book this home again.
Guest favorite
A clear swimming pool reflects the evening sky, surrounded by a spacious patio. Outdoor seating for dining is arranged under an umbrella, with chairs positioned nearby. Lush greenery provides privacy, and large glass doors lead to the inviting interior of the home.
Home in Sarasota
5 out of 5 average rating, 5 reviews

Pool, Spa, & Private Gym in the Heart of Sarasota

NatalyaRating, 5 stars6 days ago
We had a great stay at the house. Loved the interior decor. Looks like the home was remodeled recently. Everything was fresh and clean. We loved hanging out by the pool. Backyard was very private and peaceful. Posts were very quick with their responses if I had any questions about the home. We would definitely stay at the Home again when we’re in town.
Guest favorite
The exterior of the home showcases a one-story structure surrounded by a well-kept lawn. A covered parking area is present, alongside vibrant landscaping featuring various plants and trees. Clear blue skies create a bright and welcoming atmosphere.
Home in Sarasota
4.94 out of 5 average rating, 152 reviews

La Hacienda / heated pool, hot tub, 6 mi to beach

CarlynRating, 5 stars2 weeks ago
Fantastic Airbnb! Seaglass Management and Joy are great to work with. Very responsive! Great location, very safe, amazing pool and jacuzzi, close to downtown, restaurants and the Legacy bike trail. Will definitely book again in the near future.
Guest favorite
A screened outdoor area features a heated pool accompanied by a spacious seating arrangement. A dining table with chairs sits shaded under an umbrella, while lounge chairs are positioned nearby. Lush greenery provides a natural backdrop, enhancing the inviting space.
Home in Sarasota
4.96 out of 5 average rating, 142 reviews

Beautifully Remodeled Home with Pool Near Siesta

NancyRating, 5 stars2 weeks ago
You will not find a better host. We mentioned that we were celebrating a birthday and Yekaterina went above and beyond what we could have even thought of! She surprised us with all of the finishing touches. She made our stay so special! Her place is amazing! The location, the space, EVERYTHING. She is absolutely incredible and we can't say enough about Yekaterina, her place, and our stay. We have been to a lot of airbnb's and many very nice, but Yekaterina is the absolute best host you will find. You will not be disappointed! This is definitely at the top of our list of "Places to stay and visit again!" Thank you Yekaterina!
Guest favorite
A screened-in pool area is showcased, featuring a heated pool with clear blue water. Sunlight casts shadows on the tiled surface, while a picturesque view of a private lake and surrounding greenery is visible in the background.
Home in Sarasota
4.94 out of 5 average rating, 133 reviews

Lake Front House with a Pool

Jose & ZullyRating, 5 stars2 weeks ago
This house was spotless, organized and had a loaded kitchen! It is in a amazing location near the beaches and the house came loaded with beach equipment. I would love to come back. Birute was very helpful with us and responsive in timely manner Thansk for all!

Condo rentals with a pool

Guest favorite
A community pool area is highlighted, featuring a clear blue pool surrounded by lounge chairs. The yellow building with arched windows stands in the background, and palm trees add greenery to the serene environment. A sunny sky enhances the overall vibrant atmosphere.
Condo in Sarasota
4.97 out of 5 average rating, 201 reviews

Gateway to Siesta Key - 1/2 Mile to the Beach

Stephanie Rating, 5 stars1 week ago
Excellent place, unbeatable location, very cozy and comfortable. Chris let us know we could check in early without even asking. I would gladly come back!
Top guest favorite
A modern kitchen features white cabinetry and a spacious counter. Stainless steel appliances, including an oven and microwave, are visible. A decorative beach sign adorns the wall, and a bowl of fresh fruit sits on the counter, adding a pop of color to the bright space.
Condo in Siesta Key
4.85 out of 5 average rating, 173 reviews

Best Siesta Key Condo

AndrewRating, 5 stars2 weeks ago
We had a very good time at Siesta Key and enjoyed our time at Maureen's place. The building is older, the amenities are well maintained and the condo itself is well cared for. I did find some mystery stains on the mattress and the decorative pillows in my room, but I'm guessing they are just spills that were difficult to get out. More importantly, the boat dock is usable, albeit with some difficulty if the boat is larger than 22 feet or so. We figured out on the second day that the best way to dock was parallel to the intracoastal between the posts and to tie off with lines on either side of the stern and with a single line on the bow. I would check ahead to make sure the dock is available, but we had no other boats docked there on a holiday weekend. The private beach access was a lifesaver on a holiday weekend, despite the short walk required to get there. Having both intracoastal and beach access is the biggest value of the place in my opinion.
Guest favorite
The image features a sparkling blue pool surrounded by a spacious patio area. Palm trees and lush greenery enhance the scenery, while the nearby Tiki Hut provides shaded seating. The backdrop includes a serene view of the water, with boats visible in the distance under a partly cloudy sky.
Condo in Siesta Key
4.84 out of 5 average rating, 236 reviews

Cozy 1BR Beach Condo on Siesta Key!

RachelRating, 5 stars2 weeks ago
We had a wonderful time at Bill's place, very cozy and had everything we needed. Loved being able to walk to the beach and spent some time at the pool, we had so many more things we wanted to do and not enough time in the day!
Guest favorite
A spacious swimming pool is surrounded by palm trees and lounge chairs, reflecting clear blue skies. The pool area is well-maintained, and the building's balcony overlooks the pool, providing a serene atmosphere for relaxation.
Condo in Siesta Key
4.9 out of 5 average rating, 117 reviews

Crystal House on Siesta Key Beach

GeriRating, 5 stars6 days ago
Our stay with Eric was amazing! We needed a quick beach weekend and this exceeded our expectations. His unit was as described with luxury towels and bed linens. Beach closet was bonus…the cart, cooler and chairs was much needed and appreciated! I messaged Eric prior to our arrival asking if there was a volleyball in the closet so I could add to our grocery order if not. First thing I saw as we walked in the unit was a new volleyball sitting on the table awaiting our arrival! Way above and beyond! Easy check in and check out. Actually, our flight was ahead of schedule and Eric allowed us early entry to get our trip started a bit sooner! This was our first time visiting the area and definitely plan on returning and will stay here again. Thanks for a great stay!
Superhost
An inviting pool area is showcased, featuring a crescent-shaped pool with steps leading in. Surrounding lounge chairs are arranged neatly along the pool deck, with palm trees adding greenery to the scene. A small shed is visible in the background, enhancing the tropical ambiance.
Condo in Sarasota
4.91 out of 5 average rating, 115 reviews

Siesta Key - 1/2 Mile to the Beach!

SabrinaRating, 5 stars1 month ago
This condo was the perfect place to stay for my trip to Siesta Key. This condo is private in a neighborhood far enough from the hustle and bustle but close enough to get to the beach within a 5 minute drive. The condo was equipped with beach gear and all kitchen necessities. Very clean, comfortable, and felt right at home. I will definitely be booking this condo again for my next trip to my favorite beach!!
Guest favorite
A large heated pool is visible, surrounded by lounge chairs for relaxation. Tall palm trees frame the area, and the building's exterior provides a backdrop. The clear blue water reflects the sunny sky, inviting guests to enjoy a refreshing swim.
Condo in Sarasota
4.86 out of 5 average rating, 148 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

AnnRating, 5 stars1 week ago
Great stay, the location, the amenities all were wonderful. Melissa and Brandon were super responsive and the place had more essential stocked than most of the other places we have stayed, which was very thoughtful. Melissa also had a regular coffee pot sent out to us right away, since we don’t use Keurig’s which was super nice and very much appreciated. We would definitely come back!
Guest favorite
A large heated outdoor pool is surrounded by lounge chairs, offering ample space for relaxation. The pool area is framed by palm trees, with a view of the condominium building and parked cars in the background, creating a welcoming environment.
Condo in Siesta Key
4.94 out of 5 average rating, 106 reviews

Siesta Key Beach Front Condo

JessicaRating, 5 stars3 weeks ago
Our stay was exactly what we wanted. Our host, Evan, was great and quick with any questions we had. The condo was located very close to Siesta Key Beach, and we didn't have to drive more than 20 minutes to get to anything that we wanted to around that area, some things even within walking distance. Everything we could have possibly wanted was provided in our home, which really made the week stress-free. We would definitely stay here again!
Top guest favorite
A charming studio space features a queen size bed with a white blanket and decorative pillows. A small nightstand sits beside the bed, and a light is positioned for reading. Natural light enters through a large window with blinds, complementing the wood-look flooring.
Condo in Lido Key
4.96 out of 5 average rating, 140 reviews

Lido-Key- Tiny Studio Holiday Cottage-A

MarkRating, 5 stars1 month ago
I consider myself a seasoned veteran traveler… So when I walked into an Airbnb in Lido Beach, I wasn't sure what to expect actually. I pleasantly surprised. Unit number 12 is perfect for me. located in the corner of the small property where multiple units were located. Nice pool, nice shaded paths excellent landscaping it just felt good to be there :-) Every time I travel, I take an assessment of the things I need to go buy. You know simple things the kitchen or for a walk to the beach. This team had everything including the beach chairs. I would highly recommend this property. This host in this area. I just purchased a property in Sarasota area and I will try to use this spot again as my secret getaway. Awesome experience.

Quick stats about vacation rentals with a pool in South Sarasota

  • Total rentals

    210 properties

  • Nightly prices starting at

    R897 ZAR before taxes and fees

  • Total number of reviews

    5.7K reviews

  • Family-friendly rentals

    190 properties are a good fit for families

  • Pet-friendly rentals

    50 properties allow pets

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

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