
Holiday rentals with a pool in Siesta Key
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Top-rated rentals with a pool in Siesta Key
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Siesta Key rentals with a pool
House rentals with a pool

Your private retreat near Siesta Key Beach.
Excellent location, just a 10-minute drive from the beach. The house is spacious, very comfortable, and has everything you need for a relaxing stay. The pool area is beautiful and perfect for cooling off in the heat. We had a great time and would gladly return!

New remodel- 150 Yds to Beach and Restaurants!
This is our 3rd time staying here and I plan to keep going back. The home is beautiful, clean, comfortable and has everything you could need. The location is perfect! It’s our favorite vacation spot!

"Enfuego!"
Such a perfect escape for a family or a group of friends! The backyard feels like you’re in a private tropical paradise. There are so many amenities in this home you barely need to leave! On days you want to hit the beach, it’s only about 10-15 minutes to get to Anna Maria Island - very convenient location. This was one of our favorite rentals which is well documented by all the photos we took throughout the home - swimming in the pristine pool with the waterfall and fire features glowing, playing golf, watching movies in the theatre, sun bathing on the real sand beach with tiki hut, beautiful loungers and so much more! We already have ideas about the different groups of friends we want to share this property with! Such a score and the hosts are delightful too!!

Beach, Village, Dock & Private Pool! One-of-a-kind
Marko’s family home was beautiful, charming, and spotlessly clean. The home is perfectly located, walkable to beautiful beaches and great restaurants and shops, including the market. Marko was extremely hospitable, ensured we were all set and gave wonderful recommendations. We loved this place and will be back again next year. Thank you!

2bed/2bath with POOL house, close by SIESTA KEY!!!
We loved our stay! The home was just as described. It was very clean and had everything we needed for a comfortable stay. The property is a short drive from first class Siesta Key and other beaches. Romualda was an amazing host. She responded quickly to our questions and went out of her way to make us feel at home. I highly recommend!!

Rustic Sands - 650
Our time at this Airbnb in Siesta Key was amazing! The house was super clean and had an awesome kitchen with everything you could think of, plus more. Great appliances, tons of towels, dishes, some games, TVs with premium channels and more! Outside was just as great. The pool area was covered with mosquito netting, so we could relax without bugs bothering us. The pool was our favorite spot! super clean, and the outdoor BBQ grill was great! The only thing was the master bedroom bed was a bit small and not the most comfortable for us (queen size), but everything else was so good. The neighborhood was really quiet, location was 4 minute drive from the beach. Overall, this Airbnb was one of the best places we've stayed. I would 100% recommend it and would come back! it looks better in real life than the photos.

SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!
Great place, very clean and had everything we needed. Instructions very clear and the pie waiting for us in the fridge was much appreciated! The beach gear was a nice touch, just a pity the weather wasn’t kind to us.

Palm Retreat: #1 Top Rated Rental of Bradenton/AMI
This was a great home for our family of six. We hope to return again.
Condo rentals with a pool

Stunning Siesta Vistas Direct Beach Access & Pool
Amazing views!!! What a beautiful condo! We are so happy we stayed here! Pros: Very very clean, fresh and new. Plenty of towels, both bath towels and beach towels. Beds were comfortable. Kitchen was stocked nice. The pool was very nice, easily accessible, and there was a restroom in the adjacent tower for us to use. Extra toilet paper in bathrooms, extra paper towels in kitchen, and a couple laundry pods. Cons: Washer/Dryer was a one unit combo machine which was tiny. We needed to dry our beach towels because it rained while were there and could not use the unit in the condo. There are pay washers and dryers on the first floor of the tower that we had to use instead. The living room and master had cable which was a pro but the living room had a Roku that wasnt signed in so we couldnt use that. There were no scissors in the kitchen which seems insignificant until you need them. Shark teeth = drive south to Caspersen beach!!!! We did not find any at this beach

Steps away from beach and village! #1 in Siesta!
This is one of the best Airbnbs I have ever stayed in. It is perfect if you have young children. It was just me and my daughter (age 2) for the week. She loves the bunk beds and there was a stroller we used all week. The private pool is so nice and shared among the 6 condos but we had it to ourselves several times throughout the week. The beach is about an 8 minute walk from the condo. Everything you need is down the street and major grocery chains are all within 15-20 minutes. VK was super responsive and kind - this one is going in my favorites and we will definitely be back. Highly recommend!!

Beautiful White Sand Siesta Key Beach
my wife and I spent a wonderful week at Connies place , great location to the pool and beach, the unit was SPOTLESS, well equipped with anything you would need , parking spot right outside our door was great , comfy bed, really nice sand chairs for the beach, always got quick answers to any questions ( none problem related) would highly recommend for any couple looking for a perfect getaway, hoping Connie and her family are well

Bright and Beachy - Steps to the Water!
Great private beach access

Sea Club 2-Relaxing Siesta Key Condo-Siesta Sky
Such a beautiful stay with all the amenities, clear instructions and a clean place with everything you need surrounding you. Beautiful home, I appreciate the stay!

LIDO KEY 1 BR/1Bath Heated Pool 16
Had a great stay and everything was as listed. Clean and convient, quiet location, 5 minute walk to the beach. Was located right across from both pool and laundry room (quarters only) which was great. William also provided beach chairs and umbrella as well as small cooler which was exactly what I needed

Crystal House on Siesta Key Beach
We loooved it here! The space was perfect for our family. I cooked several meals and the kitchen had everything I needed. The location was convenient to grocery stores and walking distance to local restaurants and ice cream shops. The trolley stop is right at the resort so very convenient free rides to downtown Siesta Key was one of the highlights of our trip. We also grilled in the back of the resort by the bay which was nice! Oak trees all around. The pool was perfect temp. The fob didn’t work for one of the gates but there were three others we were able to get in without issue. The beds and pillows were soooo comfy. The ONLY issue we had was from the pics on the original post it appeared the walk to the closest public beach access was 2 min but it was actually 15. In the Florida heat that was rough but we pushed through! Oh and last thing, the scooters were a hit with everyone in our family. So much fun! 😆 Thank you so much for giving us an amazing stay!!

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!
Quick stats about holiday rentals with a pool in Siesta Key
Total rentals
1.4K properties
Nightly prices starting at
$100 NZD before taxes and fees
Total number of reviews
24K reviews
Family-friendly rentals
1.2K properties are a good fit for families
Pet-friendly rentals
210 properties allow pets
Rentals with dedicated workspaces
670 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
- 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
- Curtis Hixon Waterfront Park
- Splash Harbour Water Park
- North Beach At Fort DeSoto Park