
Family-friendly holiday rentals in Madeira Beach
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Top-rated family-friendly rentals in Madeira Beach
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Popular amenities for Madeira Beach family-friendly rentals
Family-friendly home rentals with a hot tub

THE HOUSE - 32 Steps to the Beach - Beautiful Clearwater Beach Home just across from the Beach - Drive to your door.
We had a great time staying here in Clearwater. SO close to the beach. Their place was clean and was ready for a family to stay. We look forward to coming back.

Spacious Home Solar-Heated Pool and Spa
Great value!! We loved the pool area and very quiet neighborhood!

Waterfront Luxury Heated Pool/Hot Tub 5 bedrooms
This home was the perfect place to stay for our family vacation. Charlie was responsive and provide incredible recommendations anytime we asked. The yard was private and secure and the neighborhood was quiet. The home has everything we needed! We didn't have to travel more than 30 minutes to beaches, delicious restaurants and ice cream. I would absolutely stay here again!

Sun, Beach Views, and Smiles!!!
Beautiful place and incredible host! Place was extremely clean and cozy, only thing is that there was no soap and shampoo on bathrooms. But other than that everything was amazing, I recommend this place and this host.

Ultra Modern Pool Home w/ rooftop private HOT TUB
Great place to stay if you are heading to a BAESBALL game or an EVENT at RAYMOND JAMES STADIUM ! This is the PERFECT spot ! An easy walk

Rooms with a Pool
my husband and I took our 3 kids here for memorial day weekend. the house in a nice quiet and clean neighborhood which we loved. we only had one problem when we arrived which was the AC was out and in Florida that can be a huge problem. but we let the host know right away and they called someone to fix it. we cooled off in their beautiful pool until it was fixed and before we went to bed we had a cool house. so thank you for your prompt response in getting that fixed. other than that the house is truly a gem. very clean, great amenities and the guidebook was a wonderful addition! my kids really enjoyed the pool and hot tub and the place is very spacious where we had our room. they pretty much had everything you could think of product wise so we didn't need to get much for our stay. we are from Florida but we don't visit Tampa often but this is a place we know we will come to visit again for sure!!! thank you Aaron and Sophie for making my family vacay and wonderful one!!

Beach Front Condo 3 bathrooms 3 bedrooms/5 beds
I loved the apartment very well equipped for everything you need to cook. The apartment has an amazing view, location is great, close to everything from restaurants, grocery stores, pharmacies, etc. I loved it!

Waterfront Beach House Steps Away from #1 Beach!
We absolutely loved this space! We do an annual girls trip to Florida and we were so incredibly happy with the house, layout, amenities, cleanliness and location. Instructions were clear and posting is exactly as described. Can walk to everything in Clearwater from here. We cannot wait to go back!!
Family- and pet-friendly home rentals

Beach Studio 5
Such a beautiful stay and so close to the beach! The place was equipped with everything you could need! Will definitely be staying here again!

Vintage Florida Beach Cottage B
Cozy place perfect for a family. Neighborhood was quiet. The beach was a flat 5ish minute walk away.

Ocean Dreaming: Waterfront Home with Heated Pool,
We would go back in a heartbeat! The house and location was perfect! Our kids loved the pool and being able to kayak and paddle board right from the dock was amazing! We saw dolphins multiple times a day and had fun fishing. The golf cart was perfect for getting to the beach and plenty of restaurants, including an ice cream shop! I would totally recommend this place!

Villa Al Golfo Pristine Waterfront Oasis
We honestly couldn’t have picked a better place to celebrate our birthdays. From the moment we arrived, the owners were so warm and inviting. They surprised us with a few welcome goodies, which was such a thoughtful touch and really made us feel at home right away. The unit was beautiful—clean, spacious, and honestly felt like a little slice of luxury. The bed was super comfortable, and the towels and bedding were incredibly soft and fresh—you can tell they really take pride in keeping everything in top shape. The view of the bay was amazing, and we got to watch dolphins swim by from the unit, which was just magical. They had canoes available for us to use, which made for a fun and peaceful afternoon out on the water. The location was perfect—just a short walk to the beach, shops, and restaurants. They gave us some great local restaurant recommendations too, and we ended up trying a few that we might have otherwise missed. Can’t wait to come back. Thanks Lyn & Frank

pet friendly on an equestrian farm
As a solo 74 year old gal with an English cocker, safety is most important. I was very comfortable and felt safe. there. Just a lovely place and nice people

Surfside Villas - Apartment B
A perfect weekend by the Gulf! We had a wonderful stay at this apartment with my family and our two dogs. The location is unbeatable—right in front of the beach, with a stunning view of the Gulf from the balcony where we enjoyed every meal while listening to the waves. The apartment was fully equipped for a beach getaway: chairs, umbrellas, even a cart to carry everything easily. That attention to detail made a big difference. On Saturday night, we grilled at the BBQ area, which was also clean and ready to use. Everything was comfortable, clean, and well thought out. Tom, the host, was very responsive and the whole process was smooth and easy. Definitely a place we’d love to come back to. Thank you for everything!

Paradise Cottage Largo Beaches 1 mile safe private
Mike and Ron are amazing! Their place IS paradise. The house the space everything is so cool and not a single detail missed. The garden is enchanted and sitting in it, you feel like you are in another world. Their house is beautiful full of history, art culture and life. I loved every second of staying here. I felt like I was home finally after a very long journey. Mike and Ron are magic and their space reflects that fully. I will cherish the conversations and moments spent here forever. Thank you god for this moment exactly as it is ❤️

Waterfront Coastal Condo 2 Blocks to Beach
We had a great time staying here. I caught myself saying that every time I’m in town, I’d try to stay here. Waking up and sitting by the dock with some coffee was pretty great. The guys working the office and the water sports were very nice also. Definitely recommend staying here for small groups!
Family-friendly home rentals with a pool

Florida Island Beauty@theBeach@with Heated Pool
The bed was SUPER comfortable! (which is VERY impt.) From the wagon, beach chairs, umbrella, , bikes you couldn't ask for anything more. The beach wasn't far and all of the information given was spot on. I looked at a lot of AIRBNBs and this one by far reached my greatest expectations! Theres so much to say about this wonderful place. Yana was super nice and accommodating in any questions we had. We will surely go back again! Thank you for a wonderful get away!

Good Times and Tan Lines @ #105intercoastal
Excellent beach place! Very spacious and quiet and clean! Easy access to the beach and the pool was an added bonus! Host has everything you would need for a great beach getaway!! Fully stocked with beach chairs, umbrella, cart, and beach toys. Even equipped with beach towels. Great location for a little quiet but close to many restaurants and bars. While a staycation for us since my own beach home was destroyed by Hurricane Helene, this was a perfect place to feel right at home.

Comfortable 2BR condo, walk to all sand beach
This condo was in a great location and has a lovely pool that is kept clean and only a few short steps away! Several beaches to choose from in close proximity. The condo was clean and stocked with everything one would need to feel at home! Greg was great and we definitely will rent from him again!

StudioCondo 2minWalk to the beach, BBQ Pool. RO109
To be completely honest - I was a little bit out off by the initial description that leaned so heavily on the "Don'ts" and restrictions being communicated. However, they didn't apply to me and I really wanted a floor level condo, so I took a chance. I'm happy to report that this unit and host exceeded my expectations in hospitality. The space was immaculate and well stocked with everything we could possibly need for beachside fun. Easy entry, comfortable spacious bed, perfect setup with extra seating, and very peaceful quiet complex. Had no issues with parking. Plenty of nearby delicious dining options and the beach was literally a hundred feet or so away. Very private clean beach - I grew up in this area and have always loved Redington for it's tranquility and peace vibes. Will definitely be marking this unit as a favorite for repeat visits! ❤️

Special August 25'- All Rooms Direct Beach Front
Great location and a nice space. My family loved the big pool area and that it was right next to the beach.

Indian Shores "Rustic" Beach Condo! 2Br/2Ba
This was our 2nd stay. Great as was the last time. It’s an easy stroll to the ocean and plenary of room for us to stretch out once we get back from any of the nearby activities.

POOL VIEW IN A MODERN CONDO - Feel at Home
We loved our stay! The hosts were great at communicating with us. Very clear instructions. Place was just like the photos. Very enjoyable stay!

Barefoot Beach Resort Gateway in Indian Shores FL
I always encourage travelers to stay in Indian Shores area to avoid the congestion of Clearwater Beach area and this condo at the Barefoot Beach Resort is perfect. The condo has excellent parking, nice pool, easy walk across the street to the beach, outdoor showers and Daria’s place was excellent! It was clean, well-furnished and tastefully designed and it has beach toys, chairs, towels, cooler and an umbrella and the best part were the peekaboo views of the ocean and the terrific air conditioning. So many places in Florida keep the A/C requirements to what is uncomfortably warm IMO and don’t mention the restrictions in the rental information and Darias place has an excellent cooling system and they allow guest to keep the temperature cool. There is construction remaining from the hurricane on ground level units but we didn’t hear a peep. Daria’s place is a definite great spot for anyone’s needs. We really enjoy the space.
Quick stats about holiday rentals that are family-friendly in Madeira Beach
Total rentals
840 properties
Nightly prices starting at
₹4,327 before taxes and fees
Total number of reviews
20K reviews
Pet-friendly rentals
100 properties allow pets
Rentals with a pool
710 properties have a pool
Rentals with dedicated workspaces
580 properties have a dedicated workspace
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- Anna Maria Island
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