
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.

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.

Retreat by the Bay-Heated Saltwater Pool
Will's place was amazing! Super clean, comfortable, and exactly as described. The location was perfect - there was so much to do nearby, from the beach, great restaurants and shops. Will was also a fantastic host: responsive and helpful. Highly recommend staying here if you're looking for a spot that's both relaxing and close to all the action!

Sarasota home featuring private salt water pool
Jessica is a wonderful host and very quick to respond to any questions. The house is beautiful and the location is perfect! My family and I could not have asked for a better vacation in beautiful Sarasota! Highly recommend!!

New! 3 Bed/3 Bath Pool Home Oasis! Great Location
⭐️⭐️⭐️⭐️⭐️ 5/5 – A Perfect Getaway! We had an incredible stay at Mario’s villa in Sarasota! The home was spotless, beautifully decorated, and had everything we needed for a relaxing and comfortable trip. The pool was absolutely amazing—clean, private, and perfect for soaking up the Florida sun. The location was great too—close to the beach, restaurants, and local markets. Mario was an outstanding host—responsive, friendly, and genuinely thoughtful. He made sure we felt welcomed and had everything we needed from start to finish. You can tell he truly cares about his guests having a great experience. Highly recommend staying here if you’re visiting Sarasota. We’re already looking forward to coming back. Thank you, Mario!

Pool Courtyard, patio w/ fire pit, 2 mls downtown
This spot was perfect! We traveled with our two young children and parents. Having the two separate spaces made the whole vacation a breeze. The pool and outside area was beautiful. Any questions we had were quickly answered and we will definitely book this spot again when we come back. Close to everything but very private!

☀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.

NEW Luxury! Townhome in Sarasota
Believe the positive reviews! We had a wonderful six night stay at this New Townhome located close to UTC with plenty of restaurants and shopping very close by. Nathan Benderson Park, Beaches, gyms & downtown Sarasota Bayfront Park & Marina Jack all within a 25min or less drive. Ed was extremely responsive & would answer any questions right away. They provided beach chairs, a cooler, beach towels and even an umbrella which was a definite plus. The home was extremely clean and we all felt very much at home. The beds were extremely comfortable and bed linens felt like higher quality & all beds had plenty of pillows. The neighborhood was very quiet with access to a nice community pool which was very close to the unit. My husband and I and our three adult daughters stayed here very comfortably and had plenty of privacy. I would highly recommend this property and host!
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!

Cozy 2 bed/2.5 bath townhome
Emily went above and beyond what I expected. I needed a cooler to go to the beach, and she also provided us with beach chairs. The house has everything you could need. There are board games. The Wi-Fi works great. I didn't use the kitchen, but it's fully equipped. I'll be back soon. Thank you so much, Emily, for your kindness and prompt response 😊

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, $225/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$2,091 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
Destinations to explore
- Pet-friendly rentals Downtown
- Rentals with a fire pit Downtown
- Fitness-friendly rentals Downtown
- Condo rentals Downtown
- Rentals with outdoor seating Downtown
- Apartment rentals Downtown
- Rentals with a patio Downtown
- Rentals with a washer and dryer Downtown
- House rentals Downtown
- Family-friendly rentals Downtown
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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
- Lido Key Beach
- Cortez 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