Family-friendly vacation rentals in Holiday

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Holiday family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favorite
The exterior of a charming blue beach house is surrounded by lush palm trees and vibrant landscaping. A spacious front yard features a green lawn and neatly trimmed bushes, while a driveway accommodates parked vehicles. Sunlight filters down, creating a warm atmosphere.
Home in Clearwater Beach
4.97 out of 5 average rating, 114 reviews

THE HOUSE - 32 Steps to the Beach - Beautiful Clearwater Beach Home just across from the Beach - Drive to your door.

SheilaRating, 5 stars2 days ago
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
Superhost
The exterior of the house is showcased, featuring a combination of light stone and bold pink accents. A spacious driveway leads to a two-car garage, while a well-maintained lawn with greenery complements the inviting entrance.
Home in Largo
4.79 out of 5 average rating, 425 reviews

Spacious Home Solar-Heated Pool and Spa

ValerieRating, 5 stars3 weeks ago
Great value!! We loved the pool area and very quiet neighborhood!
Top guest favorite
The exterior view features a well-maintained landscape with palm trees and lush greenery. A brick border outlines a mulched garden bed, enhancing the curb appeal. The entrance is flanked by a two-car garage, offering convenient parking. Sunlight brightens the scene on a clear day.
Home in Largo
4.97 out of 5 average rating, 129 reviews

Crescent Beach House Pet friendly

JenniferRating, 5 stars1 month ago
Great place and location. Lots of possibilities for day trips and some great running opportunities around the area. Great beach options very close by!
Guest favorite
A cozy living area is presented, featuring a leather sectional sofa, vibrant throw pillows, and a wooden coffee table. A television is mounted on the wall, while a fireplace adds a touch of warmth. Decorative accents include a colorful chair and a small Christmas tree.
Bungalow in Ybor City Historic District
4.76 out of 5 average rating, 313 reviews

Historic Bungalow with Private Pool in Ybor City

PatrickRating, 5 stars2 weeks ago
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.
Guest favorite
The exterior of the multi-story vacation home is shown, featuring light-colored walls with arched windows and balconies. Palm trees line the front, and a paved driveway leads to individual garages below. The rooftop terrace is visible, suggesting additional outdoor space and amenities.
Townhouse in Clearwater Beach
4.85 out of 5 average rating, 164 reviews

Luxurious, Family Beach Condo w/Rooftop Terrace-#4

PattiRating, 5 stars6 days ago
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.
Top guest favorite
Condo in Clearwater Beach
4.93 out of 5 average rating, 143 reviews

Beautiful Townhome with Private Rooftop & Hot tub

StaceyRating, 5 stars4 weeks ago
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.
Top guest favorite
A modern kitchen showcases white cabinetry with marble countertops and stainless steel appliances. Natural light floods through large windows, highlighting decorative accents and elegant floral arrangements. A central island is surrounded by bar stools, complemented by stylish area rugs beneath.
Townhouse in Clearwater Beach
5 out of 5 average rating, 116 reviews

Waterfront Beach House Steps Away from #1 Beach!

ErinRating, 5 stars1 week ago
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!
Superhost
A serene waterfront view features lush greenery surrounding calm waters. A wooden dock extends over the water, providing access to kayaks. The backdrop consists of colorful homes, reflecting a tranquil, coastal environment.
Home in Tampa
4.78 out of 5 average rating, 113 reviews

Waterfront Oasis! Kayaks,Hot Tub

TiffanyRating, 5 stars1 week ago
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

Top guest favorite
A private outdoor patio area is enclosed by a wooden fence, featuring potted plants and colorful landscaping. Two chairs and a small table are positioned for relaxation, with sunlight filtering through trees, creating a serene outdoor space.
Cottage in Dunedin
4.96 out of 5 average rating, 205 reviews

Adorable Dog-Friendly Cottage in Quaint Dunedin

Jose ManuelRating, 5 stars1 month ago
Awesome little place, roomy for our family, very well maintained, love the property location and private parking. We will definitely stay here again
Guest favorite
A covered front porch features a glass table surrounded by four metal chairs, with colorful cushions. Decker accents and a rug add a pop of color to the tiled surface. Views of the surrounding neighborhood greenery and architecture are visible beyond the railing.
Home in Tarpon Springs
4.94 out of 5 average rating, 125 reviews

Our Gemini Place: Comfort & Charm in Old Tarpon

MichaelRating, 5 stars3 weeks ago
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.
Guest favorite
A cozy living area features a blue sofa paired with a black ottoman and a small blue side table. A potted plant sits on the table, and a colorful wall art piece is displayed nearby. Natural light filters through two windows with blinds.
Guesthouse in St. Petersburg
4.85 out of 5 average rating, 477 reviews

Cute home in historic neighborhood

DeborahRating, 5 stars5 days ago
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.
Guest favorite
A well-appointed bathroom features a light-colored countertop with a sink and a mirror above. A white toilet is positioned nearby. Natural light filters through a window adorned with a patterned curtain, while a potted plant adds a touch of greenery to the space.
Home in Tampa
4.93 out of 5 average rating, 205 reviews

Rooms with a Pool

AshleyRating, 5 stars2 weeks ago
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 🏴‍☠️
Top guest favorite
A vibrant yellow building sits against a clear blue sky, surrounded by lush tropical greenery. Beach chairs are arranged on the sandy area, with umbrellas providing shade. A fire pit is visible in the foreground, inviting relaxation and gatherings, while the beach is easily accessible.
Bungalow in Indian Shores
4.92 out of 5 average rating, 212 reviews

Private Beach 2BR Bungalow *heated POOL* PETS ok

DionneRating, 5 stars1 week ago
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.
Guest favorite
A bright and airy studio space features a glass dining table surrounded by four wooden chairs. A patterned couch is positioned near the entrance, with light streaming in through window blinds. A beach-themed artwork adds a touch of coastal decor to the room.
Bungalow in Indian Shores
4.82 out of 5 average rating, 305 reviews

Cozy Unit #1 of a Two Unit Beach Bungalow

JoeRating, 5 stars1 week ago
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.
Superhost
An open living and dining area is visible, featuring a light-colored tiled floor. A modern dining table with mixed metal chairs occupies the space. Comfortably arranged seating includes a sofa and decorative accessories, with natural light filtering through windows and a ceiling fan above.
Home in North Hyde Park
4.82 out of 5 average rating, 205 reviews

Family Getaway/ King/Queen Beds/ Parking+Safe

ManuelRating, 5 stars2 weeks ago
Good place, close to downtown. Aaron was very communicative and instructions were clear.
Guest favorite
A cozy cottage is showcased, featuring a yellow exterior with white shutters. A white picket fence borders the front yard, which is adorned with green grass and shrubs. Two blue chairs are positioned on the porch, inviting relaxation.
Guesthouse in Pinellas Park
4.87 out of 5 average rating, 269 reviews

pet friendly on an equestrian farm

RoslynRating, 5 stars4 weeks ago
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

Top guest favorite
A private pool is surrounded by a spacious deck, featuring a light blue surface. The two-story guest house is visible in the background, equipped with a spiral staircase leading to the upper level. Lush green trees provide a natural backdrop.
Guesthouse in St. Petersburg
4.89 out of 5 average rating, 323 reviews

Carriage House in North St. Pete

TomRating, 5 stars3 weeks ago
Extremely friendly, gracious, and thoughtful host. Have stayed with before and will again.
Superhost
A covered swimming pool area features a clear and inviting pool, surrounded by a spacious patio with tiled flooring. Large glass doors allow natural light to flood the space, while lounge chairs are positioned nearby, offering a comfortable spot to relax.
Home in Dunedin
4.78 out of 5 average rating, 126 reviews

House of Relaxation

JacquelineRating, 5 stars1 month ago
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.
Top guest favorite
Home in Spring Hill
4.94 out of 5 average rating, 107 reviews

3BR Roman Oasis: Caesar's Place + Heated Pool

RobertRating, 5 stars4 months ago
The place was amazing. My family really enjoyed the pool and just the house in general.
Superhost
Home in Indian Rocks Beach
4.97 out of 5 average rating, 115 reviews

Ocean Dreaming: Waterfront Home with Heated Pool,

MelissaRating, 5 stars3 weeks ago
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!
Guest favorite
A spacious living room is presented with a large sectional sofa and a wooden coffee table at its center. Tall glass doors open to a balcony, allowing natural light to brighten the space. Soft-toned curtains add warmth to the room, complementing the modern decor.
Home in Clearwater Beach
4.97 out of 5 average rating, 223 reviews

Clearwater Beach Townhome w/Game Room & Boat Slip!

LeeRating, 5 stars3 days ago
Centrally located and spacious. Easy to walk to the beach and all of the restaurants in Clearwater
Superhost
A serene backyard enclosure features a heated pool with clear blue water, surrounded by green grass. A shaded seating area with a gazebo and comfortable chairs is present in the background, accompanied by a storage shed and lush landscaping with palm trees.
Bungalow in Largo
4.85 out of 5 average rating, 126 reviews

Charming Bungalow w/ Heated Pool - 10 min to beach

ReneeRating, 5 stars2 days ago
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.
Top guest favorite
A vibrant playground area is nestled under a large oak tree, featuring swings and a play structure with slides. The ground is covered with wood chips, providing a safe surface for children. Sunlight filters through the leaves, creating a pleasant outdoor environment.
Home in Tampa
4.99 out of 5 average rating, 276 reviews

Pool + Park + Private = Perfect Place

JulieRating, 5 stars2 months ago
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.
Guest favorite
Apartment in Indian Shores
4.89 out of 5 average rating, 309 reviews

Barefoot Beach Resort Gateway, Indian Shores FL

RachelRating, 5 stars2 weeks ago
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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