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

The Old Man & the Sea-Seaview 101
Amazing time! Great location! Will definitely be back!

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!

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

Pool + Park + Private = Perfect Place
This is the second time we've been able to book this home and if it's available I will book it again when we return. There is a park and walking trails across the street. The trails go along the Hillsborough River where you can see all the fun Florida birds. The accommodations are fantastic. It is clear the hosts care about details, including fluffy towels and sample shampoos and conditioners in the bathroom. I also appreciate the water pressure and quickness of the hot water tank to heat the water in the shower. This kitchen has everything you need if you want to cook. There are beach towels to use for the pool, as well comfortable deck chairs and floats. The hosts were very responsive, and asked if they could come over to clean the pool after an unusually heavy rain. Our family would love to stay there again when we visit Tampa.

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!!

5 *Waterfront Condo,3 BDR.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.

Bay Shores Yacht & Tennis Club Indian Shores FL
We had a great vacation at Mel’s place! We liked the amenities - putting green, shuffle board, pool, tennis courts, and pickle ball. Mel was great with communication and attentive when we needed him. Also, quick to respond. The condo had everything we needed. Only thing we would change is sharper knives. They were pretty dull for cooking/cutting up stuff. Overall, we really enjoyed our stay!

Waterfront condo on top floor @ Boca Ciega Resort
The condo was just what we were looking for. The kitchen was equipped with the basics and the view was wonderful. Tamara was friendly, responsive, and a great host. Would stay at her place again!
Family- and pet-friendly home rentals

Windsong 2 Wind Beneath My Wings
We had an amazing stay at this property! The location is fantastic—just steps from the sand. The home was well-equipped, and incredibly comfortable for our group. Our host was responsive and thoughtful, making check-in smooth and stress-free. They have beach chairs and umbrellas for guests to use. Highly recommend it to family or group of 7-8 looking for a peaceful beach escape."

House of Relaxation
Great home with everything we needed, we really enjoyed our stay!!

Downtown Dunedin B&B - Rustic Cabin with Pool
Great place with a huge pool and the walk to downtown and surrounding shops was a stones throw away. The host answered with any questions we had promptly and provided my girlfriend and I was an outstanding stay! I would love to stay with you guys again as soon as I can! Thanks for a great weekend in Dunedin! What an awesome little town!!

Our Gemini Place: Comfort & Charm in Old Tarpon
Gemini place was a real gem. Home was as described. Very roomy, very clean, decor top notch, very comfy and home like feel. Easy walking distance to Spring Bayou, Sponge Docks, shops and restaurants. Less than 50 years to a very spiritual moving shrine, St Michael’s. Very clean and safe neighborhood too. We absolutely loved the home and location.

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

Serene French Country Cottage near everything
We were in Dunedin for a family party, the place had plenty of spots for the seven of us to have a little alone time when needed. We all enjoyed the eclectic decor too!

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!

Steps to Beach+bikes VaCay getaway on PaG island
The Sea Breeze was perfect! A short walk to the beach and away from the touristy parts of St. Pete. The bed was very comfortable and Lisa even provided a complimentary bottle of wine. My husband and I wish we could have stayed longer!
Family-friendly home rentals with a pool

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.

Renovated Condo! Across the Street From The Beach
being 7 months pregnant this place was perfect for a quick baby moon! the beach is just a walk across the street, plenty of restaurants less than a 5 minute drive and had everything we needed for the beach as well.

Seashell Cottage
We loved the Seashell cottage! My family has stayed in the Mermaid cottage several times and thought it was the perfect “beachy” cottage but the Seashell is even bigger and better. Decorated adorably and has everything you need. Kitchen is fully stocked-all you have to do is bring your groceries. Bathrooms have plenty of towels-hairdryer also. Washer/dryer Outside patio is the perfect place to have coffee in the morning or wine in the evening. It’s plenty big with a picnic table and other chairs One of my grandkids favorite was the delicious pizza place on the corner-I believe they got one every night. We love the Shoreline cottages and I know your family will also. OH-forgot the best part-steps from the beach!! This end is less crowded and it’s perfect

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.

The Avalon - 1/1 LUXE CORNER CONDO/King size bed/
Great location, and host provided everything we could need whether it’s at the apartment or at the beach.

1 BR direct gulf front!
Due to the hurricanes there was still some work going on at the Condo and on the beach. We completely understood and knew this might be the case coming in. Our goal was to relax and unwind and that is what we did! We loved the location - the ocean view from the deck and the short walk to the beach. The bed was relatively comfortable - not too hard. There were plenty of things in the kitchen to make using it easy. We walked and hung out on the beach a lot which was our plan. The pool is small but was nice. There are restaurants and stores within relatively close driving distance. When we had a question everyone was quick to get back to us. Overall a truly wonderful experience!

Updated & MOM Clean-Waterfront-Lux 4Bed/3Ba (#202)
Bryan’s property is beautiful. This was our 2nd stay and everything was just as perfect as the year prior . The kitchen is wonderful for preparing meals , the beds were very comfortable as well as the leather sectional and everything was spotless. We enjoyed the watching the dolphins in the bay and the pool was great. The location was ideal , just a short stroll to the beach and restaurants and shops were within walking distance. This condo is truly lovely!

Beach Front Casa De Playa Unit 212
The location was perfect, right on the beach with gorgeous views from the balcony and lounge with walkable eating places. The accommodation had everything we needed and was comfortable. We really enjoyed our time there.
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- Anna Maria Island
- Weeki Wachee Springs
- Anna Maria Public Beach
- Dunedin Beach
- John's Pass
- 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
- Tampa Palms Golf & Country Club
- North Beach At Fort DeSoto Park