
Vacation rentals with a pool in Downtown, Sarasota
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Top-rated rentals with a pool in Downtown, Sarasota
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Downtown, Sarasota rentals with a pool
House rentals with a pool

New Remodeled Pool Put Put Green Mins to Beaches
Everything was great, thanks to Josh for his kind attention.

Lovely Beach Bungalow
Olga’s place is such a gem! We had a wonderful week long stay - we felt right at home the moment we stepped inside! Olga was so sweet and always made sure we had what we needed. The pool was an added bonus, it felt like we had a private oasis to hang out at after we went to the beach. The house was impeccably clean and stocked with everything you could possible need for a comfortable stay. The AC was lovely and the beds were so comfy, everything about this airbnb exceeded our expectations. We didn’t want to leave, but already can’t wait to come back one day. We highly recommend Olga’s place 😊

Luxury 3/3 with Heated Pool, Spa, & Putting Green!
Erinn was an amazing host - she would respond immediately to any text and was always friendly and helpful. The house is as good as it looks if not better! My husband complains about every airbnb I book but he even he had to admit this one was top notch.

Coastal Comfort Getaway, Heated Pool, Heart of SRQ
Vanessa and Nicole’s place was even better than we expected! It was spotless, beautifully decorated and we felt right at home. You can tell how much thought and care they put into even the little things to make guests comfortable. They were friendly and extremely proactive with communication when we reached out about a minor issue with the shower drain. We couldn’t have had a better stay and look forward to coming back in the future!

LUX Downtown/Siesta Key heated pool & great yard
5 Stars – Wonderful Stay! I had an amazing experience staying at this Airbnb! The place was spotless, beautifully decorated, and exactly as described in the listing. The bed was incredibly comfortable, and I appreciated the thoughtful touches like coffee, local guidebooks, and extra towels. The neighborhood was quiet, safe, and within a few miles away there is great restaurants and shops. Our host was friendly, responsive, and made check-in super easy. They even gave us great local recommendations that made our trip even better. I would absolutely stay here again and highly recommend it to anyone visiting the area!

The Blessing House- Htd Pool/Spa, Close to Beaches
We had a lovely stay at the Blessing House! It was plenty spacious for three adults and three kids, and had pretty much every amenity we could want. The kitchen was well-stocked with pots and pans and spices etc. which made simple cooking very easy. The house is an easy drive to Siesta Key beaches south or St. Armand's Circle/Longboat to the north, so that made it a good home base for exploring the area. Caitlyn was extremely communicative and was able to give us a little extra time upon check-out, too, which was much appreciated. I'd definitely recommend this place to others!

☀Coastal Gem☀Heated pool & amazing location!☀
This place was perfect for us. family of 4 with 2 kids age 7 and 10. They loved the pool which was bigger then it looked from the photos, was very warm and garden well maintained. really happy with stay and Carrick was quick to respond when we ask questions. asked for a later check out which Carrick was able to accommodate. Great stay would recommend.

Downtown Oasis: Poolside Condo, Patio & Gym
Stayed here for the national rowing competition for one week. The place is lovely - very clean, the complex is nice & the pool is great. It was a perfect location for us - halfway between the race course where we needed to be every day and close to downtown. The beach wasn’t far either and I liked the location and the complex very much. We felt safe and it was pretty quiet and peaceful. The owner is responsive and detail oriented with how to check in, get into the unit, etc. I would stay here again.
Condo rentals with a pool

A&A's Paradise near IMG & Anna Maria beaches
This was the most clean, most relaxing, most safe feeling place we've ever stayed in through Airbnb!! Thank you so much for such a wonderful experience. We would recommend 10/10 to anyone!!!!

Siesta Key Ground Floor Condo 2BR On Trolley Line
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!

Anchor house +6 min. from Siesta Beach+heated pool
The location was great. Easy access to the beach, grocery stores, restaurants and the pool. Doris was friendly and professional. The condo was very comfortable for my husband and I and our two grandsons. thank you, Doris. We had a wonderful time.

Charming and Updated 1 Bedroom in Runaway Bay
My fiancé and I really enjoyed our stay at David’s place in Bradenton! The space was super clean and had everything I needed for a comfortable stay. Communication was excellent throughout; the host was responsive, helpful, and always timely with their messages. One of the best parts was the beach access—super convenient, and the place was stocked with everything from a beach cart, umbrellas, chairs, and beach towels etc. which made days at the beach so easy. There were also a few great local tips provided, which I definitely took advantage of. Honestly, I wouldn’t change a thing. I’d absolutely stay here again and highly recommend it to anyone visiting the area. Thank you for a wonderful stay!

Condo with a View 1: Open Friday, $250/nt!
This condo was everything I needed and more! The location? Absolutely perfect—the beach is literally your backyard. Waking up to that ocean view the next morning was a dream. Restaurants and activities were just minutes away, which made everything so easy and fun. Heidi, the host, went above and beyond. Her communication was fast, kind, and incredibly thoughtful. She even surprised us with a delicious key lime pie and orange juice waiting for us after jet skiing—such a sweet and personal touch! I truly have no complaints. Everything about this stay was peaceful, beautiful, and seamless. I’d absolutely recommend this spot to anyone looking for a relaxing and magical beach getaway. 🌴🌊💛

Siesta Key Beach Front Condo
Another wonderful trip to Siesta! This is our third stay in one of Evan’s places, and we were not disappointed. This unit had a great view of the Gulf (this particular building has the most direct view, without the parking lot!), and the screened in lanai was amazing! As always, the unit was clean, well-stocked, and a perfect home away from home. Already counting down the days till we return!

Near beach. Daily rentals. Pool. king bed
Exactly what we wanted. Great Location, clean and comfortable condo. Super close to the beach.

Lido-Key- Tiny Studio Holiday Cottage-A
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 Downtown, Sarasota
Total rentals
30 properties
Nightly prices starting at
G$2,092 GYD before taxes and fees
Total number of reviews
770 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Vinoy Park
- Jannus Live
- Streamsong Resort
- Tampa Theatre
- ZooTampa at Lowry Park
- Curtis Hixon Waterfront Park