
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

IMG Academy-Modern Home Heated Pool Beaches 8 min
The check in is simple and check out procedure is so easy (take out trash and start dish washer).

2223 Doud Street, Sarasota, FL
This is one of the cleanest airbnbs we've stayed at. The pool was a saving grace for our 2 boys when we felt like staying in. 3 nice sized bedrooms. The location was also really great. Right in between plentiful shopping and errand running but out enough to avoid traffic. We loved it!

Large Sparkling Clean Pool Home West Bradenton
What a wonderful place! I would like to thank the host for providing an exceptional and comforting stay for me and my family. I definitely recommend this place and would return in the future. Thanks for everything!

Centrally located oasis.
The place was mostly what it said it would be, the pictures are accurate. Was pretty nice and cozy. Had lots of privacy, which was really nice. House was clean and had all of the amenities that were promised. Bed was really comfortable. The only drawback was that the pool was a little dirty, looked like it hadn’t been cleaned for a few days before we got there but it wasn’t that big of a deal.

Beautiful heated pool home, minutes from beaches
Carolina was a pleasure working with and very helpful!

Tropical Paradise - Private Pool - Close Beaches
Great place to stay, very clean, spacious, nice pool area and lovely trees/flowers surrounding the pool.. fully equipped kitchen with all and more that is needed during a stay…would recommend.

Lake Front House with a Pool
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!

Vacation Rental with private swimming pool
Absolutely loved staying here! The home was immaculately clean and stocked beyond my expectations. The pool area was private and the perfect size for two people. The neighborhood felt safe and is super close to food, shopping, etc. One of the best airbnbs I have stayed in. I would go out of my way to stay here again!
Condo rentals with a pool

Lovely Condo, Heated Pools, AMI, IMG, Top beaches
Great place to stay ,super clean, great location and all amenities were also great

Z. Water front condo, Via Roma, ground floor
This is a comfortable and clean apartment on one of the best spots on the island. The hosts were great, highly recommend.

Lovely 2 bedroom condo with pool & tennis courts
This condo was even cuter in person than it was in the photos. It was super clean, safe, spacious, had a gorgeous screened in balcony that looked out over the pool, and was centrally located really close to groceries, restaurants, multiple beaches, and more. We stayed here as a family of 4 and the kids had their own room and bathroom and we had a master with en suite. I saw another review that said there is a little noise from the busy road outside but you really only notice it if you're trying to sleep with the windows open. We originally booked a hotel that ended up being awful so I found this place last minute and they were able to get us in the very next morning. They let us check in early since we were kind of stranded, and walking in was like a breath of fresh air. Highly recommend this place for 2-4 people!

Siesta Village Short Walk to Beach w heated Pool
This place was fantastic with everything we needed. It was close to everything and a short drive to some of the other local activities. Short walk to multiple beach entrances and a cart, chairs, umbrella, etc. was all available to take to the beach. There’s a local shuttle that takes you all over the island for free and a market around the corner that’s fully stocked with everything you need to cook some meals there. We did the night time LED kayaking and then did the Mangrove Eco Tour with Kayaking SRQ, ask for Kaleb for the mangrove tour, the man knew everything about the area, its history, conservation, and gave some great restaurant and attraction recommendations in the area. Or… just hang out at the beach. We were there during tropical storm Debby and Kathryne communicated with us throughout. Absolute amazing stay… even with a tropical storm! We can’t wait to come back.

Shorewalk upgraded condo upstairs unit 4415
This was our third time at Shorewalk, but our first time at Hannah & Helens’. The condo was in a great position and had easy access from the road. We also had family and friends staying at Shorewalk in several condos and they called ours the penthouse suite as they were so impressed with it. There was even beach chairs, beach umbrella, boogie boards , wheeled coolers and beach towels. We had a small problem with a faulty faucet in one of the bathrooms, and it was quickly resolved and a replacement one fitted by a very pleasant handyman. The owner even personally called the condo to let us know the plan of action. We would definitely recommend the condo.

Lakeside Condo. Beaches, Restaurants, IMG nearby.
Stephen’s place was so great for our family. We thoroughly enjoyed ourselves. Very comfortable for everyone to stay. Great pool. The beds were comfortable. Bathrooms were so clean. We loved it for our vacation in Florida. Thank you for letting us stay!

Peaceful retreat, pool, hot tub, near Siesta Key!
My husband, daughter , and I rented Suzanne’s place for a 4 night , birthday getaway. The place has self check in and was easy to access with a code. The condo was absolutely spotless and a lot bigger than I imagined. The decor was lovely and definitely had a home feel . Tastefully decorated. The surrounding area is also beautiful and very, very peaceful. We’ve been to Sarasota before, and Suzanne‘s place is just a little bit further away from Siesta Key beach than what we’re used to but close enough that it was not a problem at all. The beds were comfortable. Check out instructions were clear and written down. I would definitely go back. Our stay was great!

Siesta Key Beach Front Condo
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!
Quick stats about vacation rentals with a pool in Downtown, Sarasota
Total rentals
30 properties
Nightly prices starting at
$10 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
- John's Pass
- Crescent Beach
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Busch Gardens Tampa Bay
- Cortez Beach
- Lido Key Beach
- Raymond James Stadium
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- Clearwater Beach
- Vinoy Park
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Tampa Theatre
- Curtis Hixon Waterfront Park
- Streamsong Resort
- ZooTampa at Lowry Park
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