
Vacation rentals with a pool in Siesta Key
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Top-rated rentals with a pool in Siesta Key
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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!

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

5 minutes to private Siesta Key Beach + 2 pools
Solen was an amazing host—very responsive, friendly, and helpful throughout our stay. She even brought us a brand-new can opener when we needed one! The house was spotless, cozy, and located in a great area. We had a wonderful time and would definitely stay again!

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!!

True Island Living House/beach/water views
This was among the most beautiful and well-appointed Airbnbs that we’ve had the pleasure of staying in! Our trip was centered around a family 60th birthday celebration and this was such a lovely backdrop for our gathering. Our primary plans were to enjoy the sunrises and gorgeous outdoor area, cooking meals on the grill and enjoying them by the pool with a view of the intercoastal waterway. As such, when we arrived to find that the grill wasn’t working properly, we were disappointed. We communicated with our host about the grill the day after our arrival, and received an immediate response. However, it ultimately required back and forth texts (some at our initiation due to not receiving an update) and three days until the handyman graciously brought over his grill to loan us. Something we learned from this trip is the importance of communicating to your hosts what it is about their place that is most important to your stay—and perhaps we should have checked on the grill specifically.

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.
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!!

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!

Siesta Dunes 1st Floor Beach Front Retreat + Bikes
We have been coming to Siesta for years and rented all over the key. Siesta Dunes is right on the beachfront. It’s large with a huge pool in the centre with tons of loungers and umbrellas and then you walk out to the massive beach. Although people say walkable to the beach, in most cases you have to cross the main road and go to the other side which is a severe pain. This is all contained and it’s important for me to have the least work possible on vacation. There’s a centre deck with bbqs overlooking the beach where everyone comes to watch the sunset. Tanya’s place is bigger than it looks on the photos with two back decks, plenty of seating inside and back out. Siesta is our home twice a year and now that we found Siesta Dunes we are booked for Christmas. The trolley is the best part of Siesta outside of the massive white beach and we always make a date night at Summer House. Tanya’s is worth staying at.

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!

The Key to a Great Vacation!
Cute, cozy condo. Close to everything on Siesta Key, and walkable to the private beach. Jen was great to work with & very responsive with communication. Affordable unit & the ability to have free cancellation up until a week before the date was a big relief as we had many potential factors leading up to the trip. Thankfully it all worked out & we were able to take our vacation & had a fabulous time!
Quick stats about vacation rentals with a pool in Siesta Key
Total rentals
1.4K properties
Nightly prices starting at
ﺩ.ﺇ220 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
- 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
- Curtis Hixon Waterfront Park
- Splash Harbour Water Park
- North Beach At Fort DeSoto Park