
Vacation rentals with a pool in Madeira Beach
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Madeira Beach
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Madeira Beach rentals with a pool
House rentals with a pool

Upscale Tampa Dream Home Pool, Golf, Pool Table
We had an awesome time at Angels place. The kids LOVED the pool and the backyard was an awesome place to hang. Everything was super clean! The one queen bed was comfortable but the other beds are pretty firm (my kids didn’t mind). Other than that, no complaints and Angel was helpful and responsive!

Oasis in Largo. Beautiful pool house, hot tub.
We loved staying at Nga’s place. Sophia who we had to contact with any issues was amazing. We ran into a few problems in the beginning but she was quick to respond and take care of it. The pool was very nice. The canal really behind the house was my husband’s favorite place to relax. A lot of wildlife which he really enjoyed. The neighborhood was quiet and neighbors were very friendly. I loved the screen in porch with a tv. We definitely would stay again if we came back in this area. I can’t say enough about how great Sophia was. You can’t go wrong renting this place.

Heated pool-Hot tub-Close to Beaches-Pet Friendly
We definitely enjoyed our Spring Break in this home! The pool was, by far, absolutely perfect! We enjoyed the outdoor area very much! Great location! They provided everything from bath/pool towels to beach chairs for a beach day! The kitchen was well stocked for cooking in, but with so many great restaurants nearby, a person even want to stay home and eat! The Manchester home is in a safe and quiet neighborhood. We enjoyed walks to the nearby parks! Don’t hesitate on this home, if it’s available, RENT IT!

4 bedroom and private pool, near to Clearwater
This was by far the best day we've had with Airbnb so far!! The house was so perfect for the price and the little amenities were so nice! They had yard games for kids to play and extra blow ups for the pool it was just such a lovely experience. The host was very responsive and understanding for adjustments that needed to be made or giving information I really enjoyed this stay!!

Modern Pool Home w Putting Green
The home was exactly how it was listed. This home was absolutely gorgeous and clean! It was in a quiet neighborhood but it was close to a lot of restaurants and stuff too. Some places were so close, you could walk. My kids enjoyed the backyard very much! We hung out all day in the pool and on the putting green. The pool is heated as well which is always a plus! The host responded so quickly, was very nice and respectful and even offered us some recommendations of things to do and places to eat! The house has more than enough towels, and small toiletries. They had some extra thoughtful toiletries in the bathroom as well that was just a nice touch! The check in and check out was super smooth and easy too! We felt very comfortable here! 10/10 recommend! And definitely worth what you pay for!

Serena Pool Home close to Indian Rocks Beach
THE PLACE WAS WONDERULL NICE POOL AREA PLENTY OF SPACE IN THE HOUSE EVERYTHING YOU NEEDED FOR THE STAY PRETTY MUCH WAS THERE

Tranquil Home. 2 minutes to Indian Rock Beach...
Gisele's place was clean and just like the pictures showed. The pool area was nice with a large Weber grill and lots of chairs . There were plenty of pool rafts in the garage for our use. Grocery stores, liquor stores, and restaurants all within a short drive and some within walking distance. The neighborhood was friendly and quiet and had a Catholic church within a 2 minute walk. We would definitely consider staying again!

Beautiful house with pool, fire pit, billiard room
It’s the little things that mean a lot. There were Kleenex boxes in each room. They provided ample storage containers for leftovers. Plenty of inflatables were available for floating. Super bonus is the Florida State park pass. It’s all in the details!
Condo rentals with a pool

POOL SIDE right on the BEACH 2 bdrm condo
This condo was perfect for our family vacation! We had everything we could have needed and our host made everything so easy.

*Waterfront *2 Bedroom Condo *Amazing Sunsets*Pool
Our family had a wonderful time at this condo! We enjoyed waking to see the ocean every day and also had enough space to relax on our vacation. Helena provides a beach bag with towels and sand toys that were a very nice touch for our beach day. The staff at the bar/restaurant were great and we also felt safe with the 24 hour security guards on duty. This place really made our trip extra special!

Welcome to your vacation home
Very nice condo. It was exactly as advertised very clean and comfortable.. I enjoyed my time there

Tiki Themed Waterfront Condo on Tampa Bay
Chris was very helpful and proactive through messages and short videos. Made everything easy. Would definitely stay again.

Lovely 2 bedrooms condo with pool in Boca Ciega
Matt was the best at explaining everything and. Was so quick. To respond and answer and questions I had as well as give me great info around the area. Would rent from him again for sure and recommend him to anyone looking for a great place and helpful with any questions you might have.

Lovely Water View Condo, Top Floor, Steps to Beach
The condo location is perfect as it's across the street from the beach but the condo overlooks the bay so it is peaceful and you don't hear any of the loud motorcycles/cars that go down the main street. I was able to find covered parking at the condo everyday so your car isn't baking in the sun. You also have access to a pool and hot tub that we used every day. You are only about a 5 min walk to St. Johns Pass - which has numerous restaurants, water activities, shopping and ice cream shops.

5 *Waterfront Condo,3 Beds,2 Baths, Pool, HOT-TUB.
The condo was beautiful. Clean and spacious. Lots of amenities. Close to the public beach, restaurants, bars, and shops. Plus David ordered a perfect week of weather for us! Wonderful.

Intracoastal | Indian Shores | Beach across street
The bnb was in the perfect location close to restaurants and shops as well as stocked with beach chairs, a cooler and more to complete our beach experience. Scott was super accommodating to our travel needs! Highly recommend and will be back!
Quick stats about vacation rentals with a pool in Madeira Beach
Total rentals
950 properties
Nightly prices starting at
$42 CAD before taxes and fees
Total number of reviews
22K reviews
Family-friendly rentals
710 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with dedicated workspaces
640 properties have a dedicated workspace
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- Crescent Beach
- John's Pass
- Cortez Beach
- Bean Point Beach
- Lido Key Beach
- Busch Gardens Tampa Bay
- Amalie Arena
- Raymond James Stadium
- North Beach
- Clearwater Beach
- Vinoy Park
- Coquina Beach
- Tampa Theatre
- Curtis Hixon Waterfront Park
- Fort De Soto Park
- ZooTampa at Lowry Park
- Myakka River State Park
- Tropicana Field
- Van Wezel Performing Arts Hall
- Clearwater Marine Aquarium
- Lakewood National Golf Club
- Splash Harbour Water Park
- Jannus Live
- Adventure Island