
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.
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Popular amenities for Madeira Beach rentals with a pool
House rentals with a pool

Tootsie’s Beachside Retreat
We came for a bachelorette trip and it was the absolute perfect space! Very accommodating, quiet neighborhood and tons of space. Definitely worth booking this house!

Insta Worthy Retreat - Heated pool-putt putt | Bar
What a beautiful home! Never a dull moment in this home. We appreciated the vintage arcade, the awesome pool, and the mini golf in the backyard, as well as the ample space to watch our shows and movies. Super clean and lots of room. This is a great stay either if you by yourself, your partner or family and friends. Also it was great to be able to have the laundry machines at our disposal. 100 out of 10.

Beautiful Tampa Bay Pool Home Near Gulf Beaches
La maison est très propre et bien situé. Nous avons adoré notre séjour. Il y avait tout le nécessaire pour passer de belles vacances.

The Ultimate Vacation Pool Home w/Tiki and Cottage
This place was great, perfect for 6 people and 2 small dogs! Loved the pool and the Cabana! My Wife and I enjoyed the cottage in back, that was special! All the Amenities were great, nothing we needed from the beginning!! Thanks Stephanie and Crew!!!

*POOL* Bar, Hottub, Central location
House was super cute. The hosts thought of everything and had everything labeled as well as a guide book. Everything was clean. The only thing I would say was inconvenient was that we had to clean the pool frequently because of the foliage. A pool guy was supposed to come but we never saw anyone come clean the pool. That’s just a minor thing though and overall we loved our stay and would stay again!

Piece of paradise in Indian Rocks Beach.
Loved the house, location, pool, and hot tub! Short walk to the beach. Dinner was delivered our first night which was incredibly thoughtful and convenient after traveling all day! Overall a great experience! Would definitely recommend

Heated Pool & Hot Tub 0.7 mile from Beach
This Airbnb was a perfect location for a beach trip! Super close to several great locations, food, and fun. The hosts are very responsive and welcoming.

Stunning views! Spot dolphins from the pool!
This home was everything we hoped for and more. The views with the pool overlooking the dock and water were absolutely breathtaking. We even spotted dolphins swimming by, which made the experience truly magical. The entire property was spotless, with beautiful fixtures and thoughtful touches throughout. From the layout to the amenities, everything was curated for comfort and ease. It felt like a private luxury retreat. We couldn’t have asked for a better stay and would return in a heartbeat!
Condo rentals with a pool

Penthouse,intercoastal, 3/3 views/heated pool
We walked in and immediately felt happy and welcomed! Was bright, sparkling and clean and we felt almost spoiled by such a beautiful place! It accommodated our family of 12 nicely! The deck was relaxing and beach just a short walk. We enjoyed the heated pool as well! Our family really enjoyed our time together here. This penthouse was a highlight of our vacation! There is a grocery store next door……. Very convenient

Madeira Beach Gem
We had a wonderful first family vacation to the beach. Our 5 and 3 year old had a great time. They were a little nervous about the ocean at first but they really enjoyed the nice pool. There were tons of beautiful shells for the kids to find and plenty of beach toys. The condo felt just like home, easy to prepare meals and comfortable for sleep. It was very clean and well kept. We really appreciated the box fan for the kids room to help dull some of the noise. It was so fantastic to be able to walk out to the beach and pool several times a day. The pool and patio were cleaned daily as well. We would definitely recommend staying here and would book with Tanya again!

INCREDIBLE SUNSET BEACH OCEANFRONT TOP FLOOR CONDO
Beautiful view of the Gulf of America to watch dolphins, shipping carriers and cruise ships coming and going. The beach area is mostly crushed shells until you get to the water. Nice seeing the beach was patrolled by police regularly even in a gated area. Was able to see Manatee in the canal and watch fishing boats coming and going. Parking was easy. Condo is very clean and well decorated with that comfortable relaxing feeling - we enjoyed the balcony for awesome sunsets and star gazing or our morning coffee. The restaurant/bars are not within walking distance but were only a short drive (all of them had good food). You pay by card for parking at most locations. We would definitely stay at this beautiful location again - one of my most relaxing trips.

Luxury Beach Condo - 3BR/3BA
Fantastic place with everything you need. Five minute walk to everything (restaurants, beach, grocery store). Hosts were great with instructions, recommendations and communication. I hope to stay here again soon.

Madeira Beach getaway; walk to the beach
Wow great place and great hosts!! Conrad had no problem adjusting checkout time because we lost two days of our trip because of Tropical Storm Debbie and our plane was to leave much later that day. They also got in touch with us to see if we were doing well and if we needed anything because of the storm. Place was well equipped. We were 6 and it was great to have a shower that had its own door so that others could get ready in the bathroom. There was a half bathroom downstairs too! Just minutes to the beach, Dollar Tree, liquor store and Winn Dixie!! We would definitely stay here again!!

Beachfront building across from Johns Pass Village
We had a lovely stay. The condo was clean and conveniently located right next to the beach and had great entertainment and meal options right across the street. Pamela was very accommodating and attentive to our needs as well as being extremely friendly and quick to respond. Highly recommended!

Beachfront Madeira Norte | Gulf front | Pool
Loved our time here! The condo is clean and well-maintained. There were plenty of beach towels and toys available in the unit. The beachfront view is beautiful! The host is also very responsive & friendly. Butterball, the feline groundskeeper greeted us when we arrived. Highly recommend!!

Modern Beachfront condo overlooking Mad Beach
We had a great stay. Very comforting. There were chairs for the beach, including beach towels which is really helpful to not have to pack. The pool was amazing as well. Jennifer is very friendly and responsive.
Quick stats about vacation rentals with a pool in Madeira Beach
Total rentals
950 properties
Nightly prices starting at
G$6,273 GYD 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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- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Dunedin Beach
- Crescent Beach
- John's Pass
- Turtle 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
- Vinoy Park
- Jannus Live
- Tampa Theatre
- ZooTampa at Lowry Park
- Curtis Hixon Waterfront Park
- Adventure Island
- Splash Harbour Water Park