
Family-friendly vacation rentals in Holiday
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Top-rated family-friendly rentals in Holiday
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
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Popular amenities for Holiday 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.
This place was perfect for us and three young kids. We spent wonderful, fun-filled days at the beach. We could easily go back to the house for lunch, rest time, stuff we forgot, etc…My son’s family stayed a block away with three young kids also. We all used the many amenities of our beach shed: chairs, umbrellas, boogie boards, toys, noodles, coolers and more. The free washer/dryer was used often. The house itself was very clean, bright and comfortable. Two full bathrooms were ideal for our gang. The kids loved the patio for their meals, games and hanging out. We didn’t use the grill or hot tub this visit but they are great additions to the outdoor space. The location is perfect for the beach access but also to get into town. We were always glad to get out of the traffic and crowds to return to the peaceful home. Evening sunsets were spectacular! We had many photo ops of the family, photos that we will treasure forever. We plan to return next year and are already looking forward to it

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

Crescent Beach House Pet friendly
Great place and location. Lots of possibilities for day trips and some great running opportunities around the area. Great beach options very close by!

Historic Bungalow with Private Pool in Ybor City
Awesome place to stay! Super fun outdoor space with plenty of seating, and as you can see in the listing, an outdoor bar/TV, hot tub, and pool. Diane and her co-hosts were very helpful, especially when we couldn’t get the hot tub working. Only thing to be aware of is that the roosters can get crowing very early in the morning. Excellent stay and would absolutely come back.

Luxurious, Family Beach Condo w/Rooftop Terrace-#4
Beautiful home with stunning views of the ocean! The location was perfect, and our family loved it! We would definitely recommend this property to others! The beach chairs provided were a HUGE plus, and the host was very responsive.

Beautiful Townhome with Private Rooftop & Hot tub
We had a wonderful stay at Jades beautiful townhouse. We loved the rooftop area with all of its amenities. There is great and comfortable furniture, bed linens, extra blankets and sheets and the pretty beach towels were so much appreciated. We had everything we needed for our vacation. The decor is so tasteful and her instructions and communication were perfect!!! We cannot wait to return to Clearwater and Jades home away from home.

Waterfront Beach House Steps Away from #1 Beach!
We had the perfect stay, from the accommodations to the location, our families were extremely comfortable and relaxed! The host was courteous and communicative, and went above and beyond to ensure we had everything we needed. We even brought our boat, which was an incredible touch and allowed us the opportunity to explore the area by water, as well as enjoy a quick walk to the hustle and bustle of Clearwater Beach. Highly recommend!

Waterfront Oasis! Kayaks,Hot Tub
We went to Tampa for a business trip, but didn’t want to stay in a hotel. We chose this place because of the location on the water and the kayaks. We spent almost all of our time on the water and fishing. The house was located close to everything you would possibly need, but once you were out back you forgot you were close to the city! The hosts were super responsive anytime I messaged with questions. The house was very comfortable. AC was cold. Comfortable bed. We would definitely stay again!
Family- and pet-friendly home rentals

Adorable Dog-Friendly Cottage in Quaint Dunedin
Awesome little place, roomy for our family, very well maintained, love the property location and private parking. We will definitely stay here again

Our Gemini Place: Comfort & Charm in Old Tarpon
We enjoyed our stay at Beth’s place. The house was squeaky clean and we felt at home. The neighborhood is quiet and feels safe. We had our dog with us and she was welcomed in Beth’s home and we really appreciated that option. It is the perfect location for a visit to Tarpon Springs. It was an easy walk to town which has a couple local coffee shops, restaurants and even a book store; And an even shorter walk to the Sponge docks.

Cute home in historic neighborhood
A friend and I unfamiliar with the area spent one night to attend a concert. The place was as described. It had off street parking. Was quiet and comfortable. St. Petersburg was charming. It was in a historic area with some brick streets and alleys. Beautiful homes large and small. A vibrant area with access to so much. Loved it.

Rooms with a Pool
A few things really stood out to us in the best way possible! The host went above and beyond with thoughtful touches we didn’t expect—like complimentary drinks, a fully stocked bar with the essentials, and even mini cupcakes! We thoroughly enjoyed the pool and hot tub, which made our stay even more relaxing. The binder of recommendations was super helpful—it included great local spots to eat, nearby attractions, and things to do in Clearwater, Tampa, and St. Pete. We also appreciated the clear instructions on how to use the pool and hot tub heating system. Overall, it was a fantastic stay! P.s. you might find a hidden secret treasure too! I did 🏴☠️

Private Beach 2BR Bungalow *heated POOL* PETS ok
What a treasure. Everything was so clean & inviting. We have stayed at the Mermaid 2 x's when we had a larger group & this time it was us 2 our 2 furbabies. We absolutely loved the Dolphin layout. So cozy & peaceful. Liz is a such a caring fun host. We loved sitting outside of the bungalow in the mornings having our coffee & headed to Liz's private beach area during the day. We even got to watch new palm trees being planted since the hurricane damage the old ones. Aslo met nice ppl & their furbabies. We absolutely love Liz & her gorgeous establishment. Thanks Liz. See you & your furbabies next year.

Cozy Unit #1 of a Two Unit Beach Bungalow
This cozy and well-equipped bungalow, just steps from a clean and peaceful beach, was perfect for four guests. It featured new appliances, bedding, and beach gear, with shops and restaurants within walking distance. The hosts were great, and we would love to return.

Family Getaway/ King/Queen Beds/ Parking+Safe
Good place, close to downtown. Aaron was very communicative and instructions were clear.

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
Family-friendly home rentals with a pool

Carriage House in North St. Pete
Extremely friendly, gracious, and thoughtful host. Have stayed with before and will again.

House of Relaxation
I couldn’t have asked for a better first experience with an Airbnb! The house was beautiful and was exactly as described. It had all the comforts of home and made our holiday easy and worry free. The outdoor patio with the fabulous pool was definitely a highlight! I would recommend this place to family and friends, and even hope to return myself someday.

3BR Roman Oasis: Caesar's Place + Heated Pool
The place was amazing. My family really enjoyed the pool and just the house in general.

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!

Clearwater Beach Townhome w/Game Room & Boat Slip!
Centrally located and spacious. Easy to walk to the beach and all of the restaurants in Clearwater

Charming Bungalow w/ Heated Pool - 10 min to beach
All went well. Very comfortable stay. Home was clean with clear instructions to everything we needed. Although the pool was small, we enjoyed it. Jess did a good job of communicating with us and kept us informed throughout our stay.

Pool + Park + Private = Perfect Place
Matthews place was the PERFECT place....they have thought of everything anyone could need and have supplied it in this home! It was very peaceful and relaxing. With the park right down the street, it makes for a great place to stay. Lots of places within walking distance, and they have let you know all the walkable places to go.

Barefoot Beach Resort Gateway, Indian Shores FL
Daria’s place was fantastic! Right across the street from the beach. A couple of coffee shops within walking distance. She had chairs and beach towels available. It was a wonderful, peaceful and relaxing time.
Quick stats about vacation rentals that are family-friendly in Holiday
Total rentals
80 properties
Nightly prices starting at
ﺩ.ﺇ110 before taxes and fees
Total number of reviews
2.4K reviews
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
30 properties have a pool
Rentals with dedicated workspaces
40 properties have a dedicated workspace
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- John's Pass
- Bean Point Beach
- Busch Gardens Tampa Bay
- Amalie Arena
- Raymond James Stadium
- North Beach
- Clearwater Beach
- Vinoy Park
- Fort De Soto Park
- Tampa Theatre
- Curtis Hixon Waterfront Park
- Plantation Inn and Golf Resort
- Jannus Live
- ZooTampa at Lowry Park
- Splash Harbour Water Park
- Adventure Island
- Fort Island Beach
- Alafia River State Park
- River Strand Golf and Country Club
- Clearwater Marine Aquarium
- Fred Howard Park
- Tampa Palms Golf & Country Club
- Tropicana Field
- North Beach At Fort DeSoto Park