
Holiday 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 had a great stay! Easy check in, great communication, lovely accommodations and amenities, and so close to the beach!

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.

Cozy Tampa Home with Large Heated Pool
Dayanna is a great host. Quick to answer questions, issues, food recommendations. Will definitely want to book this as a family getaway in the future.

The Ultimate Vacation Pool Home w/Tiki and Cottage
The house is very nice, everything was very clean. We appreciate being able to check in earlier. It’s a very quiet, comfortable, and safe space. We would definitely come back.

*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!
Apartment rentals with a pool

COASTAL CHIC! Luxury Apartment with Oceanviews
I would definitely stay here again! The place was clean & everything we needed was available. The Host was very helpful with any requests or questions I had. The view is amazing! I look forward to next time!

Gulf view Condo with pool in Clearwater/St. Pete
I stayed for 5 nights at this Airbnb, it was easy to find and get into with the pictures and thorough instructions! When I walked in everything was just like the pictures and it was very clean and comfortable. It is small like she says but it worked perfectly for my friend and I. The walk to the beach is super close and the trolley system is really helpful if you can’t or don’t want to drive to nearby places. The host was very friendly and responsive, I would definitely recommend staying here and would go back!

2MinWalkToBeach/HeatedPool/Balcony/BeachGear/Cart
We had a fantastic stay! The location is perfect—right off Gulf Blvd and just a short, easy walk to the beach. The amenities were exactly what we needed, and the beach wagon was especially helpful for carrying our things. There are several food options within walking distance, which was super convenient. But the real highlight was just a short drive down the road—an ice cream shop with 150 flavors! We ended up going back multiple times because it was that good. The beach access path has some damage (as do many spots in the area due to last year’s hurricane), but it was still completely manageable, and the wagon handled it just fine. One thing to note: Gulf Blvd can get pretty busy, especially in the mornings, so light sleepers might want to bring a sound machine or something to help drown out the traffic noise. Overall, we had a great experience and would absolutely stay here again!

White Sand Beachfront Condo with Stunning Sunsets
The condo was beautiful and the location was splendid. Description was perfect. Cannot beat the views. Will definitely go back.

Royal Orleans at Redington Beach ( Studio 203 )
My husband and I just got back from the Royal Orleans staying in Marina's unit. This is our 2nd trip to the area, and we love more each time. Marina was very responsive, and flexible as they switched our flights a few times. The unit is very clean, very nice bedding, and towels! Towels were nicer then some hotels we've stayed at! Unit had everything we needed for the week!

Beautiful Studio on the paradise white sand beach!
Great little place! It is cozy and quiet with most everything you’ll need. It is small but looks exactly like the photos. The bed was very comfy and the little kitchenette was perfect for coffee and quick bites. We will stay again.

Ideal beach getaway condo!
This place was very cute and a short walk to the beach. Host was very quick to respond with any questions we had!

Sunset Serenity: Beach Condo steps from Johns Pass
We loved our stay! A beautifully renovated condo, perfect for our family, very clean, and the views from the balcony were absolutely incredible!! Amazing sunsets every night and live music nearby made this a true gem and amazing vacation spot. Walking distance to shops, ice cream, restaurants, and the most beautiful beach and clean, well maintained pool!! This place had everything!!
Quick stats about holiday rentals with a pool in Madeira Beach
Total rentals
950 properties
Nightly prices starting at
₹2,597 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
- Cortez Beach
- Lido Key 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