Vacation rentals with a pool in Madeira Beach

Find and book unique homes with a pool on Airbnb

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Popular amenities for Madeira Beach rentals with a pool

House rentals with a pool

Guest favourite
Home in Tampa
4.96 out of 5 average rating, 50 reviews

Upscale Tampa Dream Home Pool, Golf, Pool Table

JustineRating, 5 stars1 week ago
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!
Guest favourite
Home in Largo
5 out of 5 average rating, 5 reviews

Oasis in Largo. Beautiful pool house, hot tub.

PeggyRating, 5 stars1 week ago
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.
Guest favourite
Home in Clearwater
4.92 out of 5 average rating, 93 reviews

Heated pool-Hot tub-Close to Beaches-Pet Friendly

GretchenRating, 5 stars2 weeks ago
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!
Top guest favourite
Home in Seminole
4.92 out of 5 average rating, 113 reviews

4 bedroom and private pool, near to Clearwater

AprilRating, 5 stars2 weeks ago
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!!
Guest favourite
Home in Largo
4.98 out of 5 average rating, 41 reviews

Modern Pool Home w Putting Green

SamanthaRating, 5 stars1 week ago
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!
Guest favourite
Home in Largo
4.93 out of 5 average rating, 58 reviews

Serena Pool Home close to Indian Rocks Beach

IreneRating, 5 stars3 months ago
THE PLACE WAS WONDERULL NICE POOL AREA PLENTY OF SPACE IN THE HOUSE EVERYTHING YOU NEEDED FOR THE STAY PRETTY MUCH WAS THERE
Guest favourite
Home in Largo
4.81 out of 5 average rating, 80 reviews

Tranquil Home. 2 minutes to Indian Rock Beach...

TerrenceRating, 5 stars4 weeks ago
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!
Top guest favourite
Home in Palm Harbor
5 out of 5 average rating, 35 reviews

Beautiful house with pool, fire pit, billiard room

NatalieRating, 5 stars1 month ago
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

Superhost
Condo in Indian Shores
4.9 out of 5 average rating, 20 reviews

POOL SIDE right on the BEACH 2 bdrm condo

CaseyRating, 5 stars3 months ago
This condo was perfect for our family vacation! We had everything we could have needed and our host made everything so easy.
Guest favourite
Condo in Tampa
4.92 out of 5 average rating, 78 reviews

*Waterfront *2 Bedroom Condo *Amazing Sunsets*Pool

KatrenaRating, 5 stars3 weeks ago
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!
Top guest favourite
Condo in Clearwater
4.96 out of 5 average rating, 80 reviews

Welcome to your vacation home

GrantRating, 5 stars5 months ago
Very nice condo. It was exactly as advertised very clean and comfortable.. I enjoyed my time there
Top guest favourite
Condo in Tampa
4.97 out of 5 average rating, 148 reviews

Tiki Themed Waterfront Condo on Tampa Bay

PatriceRating, 5 stars1 day ago
Chris was very helpful and proactive through messages and short videos. Made everything easy. Would definitely stay again.
Guest favourite
Condo in St. Petersburg
4.91 out of 5 average rating, 23 reviews

Lovely 2 bedrooms condo with pool in Boca Ciega

JohnRating, 5 stars9 months ago
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.
Superhost
Condo in Madeira Beach
4.83 out of 5 average rating, 138 reviews

Lovely Water View Condo, Top Floor, Steps to Beach

NeilRating, 5 stars4 days ago
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.
Top guest favourite
Condo in Clearwater
4.93 out of 5 average rating, 145 reviews

5 *Waterfront Condo,3 Beds,2 Baths, Pool, HOT-TUB.

RobertRating, 5 stars4 days ago
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.
Guest favourite
Condo in Indian Shores
4.88 out of 5 average rating, 52 reviews

Intracoastal | Indian Shores | Beach across street

LizRating, 5 stars2 weeks ago
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

Destinations to explore