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Family-friendly vacation rentals in Holiday

Find and book unique family-friendly homes on Airbnb

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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The charming exterior of the home is showcased at dusk, with warm lighting illuminating the entrance and garden. The driveway leads to a single-car garage, while solar-powered lights line the path, enhancing the inviting appearance of this mid-century oasis.

Home in Holiday

4.95 out of 5 average rating, 216 reviews

King Bed Ensuite+Queen 2/2/1—2 Living Spaces+4TVs

Step through the cheery door into your 2BD/2BA mid-century oasis. This home provides an elegant, yet comfortable vibe while featuring lavish amenities including 4 Smart TVs, a fully equipped kitchen, 2 living spaces, a dedicated workspace, a master ensuite, luxury mattresses, private patio, garage parking, a washer & dryer. Enjoy all the comforts while being minutes to grocery stores, restaurants, Tarpon Springs/Sponge Docks(4.9mi) Anclote Beach(4.8mi) Honeymoon Island State Park(16.2mi) & more!

Top guest favorite

The image showcases a tranquil bedroom area with a queen-sized bed adorned with botanical-themed bedding. A sofa is positioned beside the bed, complemented by wall art featuring greenery. The backdrop features a serene outdoors view of trees and grassy space, creating a sense of privacy.

Apartment in Port Richey

5 out of 5 average rating, 138 reviews

Jungle Studio. Private with Separate Entry & Patio

PRIVACY & COMFORT AT THE BEST PRICE. Country setting near everything. Experience affordability & convenience with NO extra fees! Enjoy peace and quietness at this spacious retreat. Separate entry & FREE parking. Just 10 mins to hospitals, near highways, restaurants & shops Features a queen bed, 45" TV with FREE Netflix, full kitchen, dinning area & full bathroom, high-speed internet, & private, fenced patio. Perfect x travel nurses, business trips, golfers, romantic getaways, or visiting family

Top guest favorite

A screened-in lanai features a heated saltwater pool surrounded by colorful outdoor furniture. Children’s toys and pool floats are placed nearby, alongside a small bike. The serene space is perfect for relaxation and play, with trees visible beyond the enclosure.

Home in Palm Harbor

5 out of 5 average rating, 111 reviews

Coastal Escape: heated saltwater pool & beaches

★ Close to beaches - Honeymoon Island: just 6 miles away. - Clearwater Beach: 15 miles away - crowned the nation's #1 beach Trip Advisor in 2018 ★ Heated saltwater pool ★ Screened-in lanai ★ BBQ grill ★ Large backyard w/ playground ★ Outdoor dining area ★ 3 bedrooms New Mattresses - California king size bed - Queen size bed - Kid-friendly room w/ two bunk beds ★ Renovated kitchen and bathrooms ★ Open living space - great for family gatherings, movie nights ★ Children toys and games

Top guest favorite

The exterior of the cabin is showcased, featuring a white façade and a welcoming front porch. Decorated with colorful plants, the walkway leads to the entrance, framed by lush greenery and tall trees providing natural shade.

Cottage in Tarpon Springs

4.98 out of 5 average rating, 116 reviews

Cooper Cabin: Cute, Adorable, Standalone Studio

Cooper Cabin is a super cute and sparkling clean stand alone studio with a full eat-in kitchen and bath. Due to allergies of visiting family & friends we do NOT ALLOW PETS OR COMPANION ANIMALS, so you can rest assured that animal allergens will NOT be an issue! Located within walking distance of all things Tarpon Springs and just a short 7 min drive to Fred Howard Beach, Cooper Cabin is decorated with fun decor and a relaxing front porch balcony with bistro set. Bikes and beach gear provided!

Top guest favorite

A cozy living room is displayed with a green sofa positioned beside a plant. A coffee table sits at the center, accompanied by a light fixture and a wall art piece. Natural light filters through the window, illuminating the warm wood flooring.

Vacation home in Tarpon Springs

4.98 out of 5 average rating, 106 reviews

Modern Home Great Location

Welcome to your home away from home. Our guests’ comfort is our priority. Equipped with all your creature comforts and surrounded by modern fixtures and decor to ensure a wonderful vacation. Open Floor plan, huge kitchen, and two cozy bedrooms. Walking distance to all the local restaurants and attractions, without the noise to keep you up at night; you couldn't choose a better location Please note: this is a duplex property, so you'll be sharing the building but enjoying your own private space.

The entrance of Palm Cottage features a welcoming red double door with decorative glass panels. Lush green plants and white gravel provide a fresh outdoor aesthetic, complementing the blue siding of the cottage.

Cottage in Tarpon Springs

4.83 out of 5 average rating, 111 reviews

Palm Cottage * King Bed * Tropical Yard

Located in the heart of historic downtown Tarpon Springs, Palm Cottage (520 sf) is walking distance to the world famous SPONGE DOCKS, and located just blocks away from breweries, restaurants, and the PINELLAS TRAIL. And the BEACH is only 3 mi away! The cottage offers king and twin beds, Wi-Fi, Fire TV, kitchen w/ full stove and fridge, coffee maker, toaster, pots, pans, table, and shared use of the tropical back yard of our 121-year-old Victorian home. 1st time Airbnb guests welcome!

Top guest favorite

The guesthouse is set on a green lawn, surrounded by trees. A friendly horse grazes nearby, accompanied by a variety of free-ranging chickens and ducks. The exterior features a welcoming porch with wooden railings, adding to the farm's relaxed atmosphere.

Farm stay in Zephyrhills

5 out of 5 average rating, 199 reviews

HORSE FARM Retreat, Newer Built Private Guesthouse

Escape to our private guesthouse located in our peaceful but lively 7-acre farm with our family of horses, ponies, Guinea hens, ducks, roosters, chickens, bunnies, cats, & very lovable dogs. Enjoy grabbing fresh eggs, giving animals treats, puppies belly rubs, grilling, making s’mores at the fire pit, and enjoying the farm life! PLEASE read entire listing if little ones will be joining :-) NOTE: Our horses are not available for riding (see our guidebook for great alternate options)

The exterior features a light grey cottage with a blue door and an American flag displayed prominently. Two wire chairs are situated on a gravel porch area, bordered by white fences and a small palm plant. The landscape is lush, providing a welcoming entrance.

Home in New Port Richey

4.83 out of 5 average rating, 119 reviews

Downtown NPR Studio Private Home in Downtown!

You will love staying at this newly remodeled studio home minutes from Downtown New Port Richey,FL. Walking distance to the beautiful downtown area where you will find many great restaurants including: The Social, Kazu Sushi, and Hershel's Scratch Kitchen. Enjoy a drink at the many bars and breweries within walking distance. Visit Sims Park on the Cotee River, let your kids enjoy one of the best playgrounds around with splash pad all without having to even get in your car!

Top guest favorite

An outdoor seating area is situated on a lawn, featuring a small black table and two chairs. The view includes the serene Pithlachascotee River, along with a dock and decorative features, framed by lush trees and greenery.

Guesthouse in New Port Richey

5 out of 5 average rating, 180 reviews

Palm Hideaway on the Cotee River

Relax on the river at Palm Hideaway-a luxury escape to the Gateway of Tropical Florida. Our cozy guest cottage is nestled amid lush greenery on the Pithlachascotee "Cotee" River in New Port Richey. Sleep in the king size bed & have coffee or tea on your Tiki patio rain or shine. Guests have shared access to the river from the park-like backyard & can enjoy the fire pit or paddle the kayaks.

A clear view of the heated private pool, surrounded by a screened enclosure. The water is inviting with a light blue hue. Colorful pool floats and lounge chairs are visible, providing ample space for relaxation.

Home in Holiday

4.92 out of 5 average rating, 111 reviews

Tropical Escape • Pool + Beaches Nearby (5min)

🌴 Escape to your private Florida oasis ☀️ Enjoy a home with a private pool, fast WiFi, workspace, and full kitchen. Located near Tarpon Springs, Dunedin, Clearwater, and Tampa, with easy access to natural parks perfect for hiking and exploring. Relax, recharge, and make unforgettable memories. 🎯 Book now and experience the perfect getaway! 🌊🌿

Top guest favorite

A cozy sleeping area is presented with a spacious bed covered in golf-themed bedding. A light-colored accent wall complements the wood-like flooring. Natural light enters through a window featuring blinds. Additional decor includes subtle golf-themed artwork and a closet unit in the corner.

Tiny home in Port Richey

4.98 out of 5 average rating, 128 reviews

Golf-Themed Tiny Home w/ Private Entrance & Patio

Welcome to The 19th Hole Suite! Escape to your own cozy retreat at The 19th Hole, a fully detached tiny home designed for total privacy and relaxation. Whether you’re traveling for work, passing through, or planning a peaceful getaway, you’ll love the comfort, quiet, and fun touches we’ve added just for you.

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Unique stays

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Popular amenities for Holiday family-friendly rentals

Free parking on premises

Air conditioning

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

4.98 out of 5 average rating, 123 reviews

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

A charming farmhouse exterior is showcased under large trees, with a welcoming front porch featuring red seating and decorative plants. A spacious gravel parking area is visible, complemented by a green landscape in the background, enhancing the tranquil setting.

Home in Palm Harbor

4.9 out of 5 average rating, 126 reviews

Renovated peaceful 2 Bed cottage with/hot tub.

A spacious living area features a light brown sofa and wooden accents throughout. Colorful wall decorations and plants create a vibrant atmosphere. A dining table is positioned nearby, and an open kitchen is visible in the background. Light streams in from large windows adorned with blue curtains.

Bungalow in Ybor City Historic District

4.99 out of 5 average rating, 318 reviews

Cozy AF Jungle-House Hideaway

Top guest favorite

An outdoor tiki hut porch is illuminated by soft string lights. Comfortable seating creates a cozy gathering area, surrounded by lush greenery. A wooden dining table sits in the center, offering a relaxed space for meals or conversation.

Guesthouse in Dunedin

4.96 out of 5 average rating, 186 reviews

Tiki Hut Cottage

Top guest favorite

A spacious living area is furnished with a large sectional sofa and additional seating, centered around a rustic coffee table. Large windows provide natural light, while a ceiling fan adds comfort. An open layout connects to a dining area and kitchen in the background.

Home in Tarpon Springs

4.96 out of 5 average rating, 367 reviews

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens

A neatly maintained outdoor space features a lawn area with synthetic grass. A cornhole game board with colorful stripes is positioned on the lawn. Enclosed by a wooden fence, a gated area is visible, indicating a private and secure environment.

Home in Seminole

4.95 out of 5 average rating, 122 reviews

Heated Pool & Hot Tub 0.7 mile from Beach

A refreshing pool with clear turquoise water is surrounded by a stone patio. Two chairs and a small table are positioned near the pool, providing a space for relaxation. The entrance to the guest suite is visible through glass doors, framed by natural greenery.

Guest suite in Hudson

4.91 out of 5 average rating, 176 reviews

UVlite sanitized guest suite w/private entrance.

Top guest favorite

A spacious outdoor pool area is visible, featuring a large swimming pool surrounded by lounge chairs and seating areas. A pergola provides shade, while decorative planters add greenery. The area is enclosed by a privacy fence, creating a secluded retreat.

Home in Seminole

4.99 out of 5 average rating, 314 reviews

UTOPIA!Heated Pool &Hot Tub 2 master suites w KING

Family- and pet-friendly home rentals

A serene sleeping area features a large bed adorned with multi-colored striped blankets and a cozy yellow throw. Natural light fills the space through two windows, illuminating the wooden accents and white walls.

Tiny home in Tarpon Springs

4.88 out of 5 average rating, 261 reviews

Driftwood Surf Shack

The collage showcases the cowboy pool surrounded by pebbled landscaping, a cozy bedroom with a spacious bed, a stylish living area with ample seating, and a fully equipped kitchen. Vibrant beach chairs and outdoor games are also visible, highlighting a welcoming atmosphere for relaxation and entertainment.

Home in Holiday

4.91 out of 5 average rating, 76 reviews

Lazy Day Oasis

Top guest favorite

A spacious backyard is highlighted by a hammock suspended between two trees, inviting relaxation. A black dog and a tan dog can be seen exploring the grassy area, surrounded by tall trees adorned with Spanish moss. A guesthouse is visible in the background.

Farm stay in Odessa

4.98 out of 5 average rating, 186 reviews

Farm and lake stay at Malfini Cay

Top guest favorite

The tiny home is set amidst a lush forest backdrop, featuring a welcoming entrance that is framed by large windows. A spacious wooden deck is adorned with comfortable seating, including two bright blue chairs and two red chairs. A black hammock hangs between trees, inviting relaxation.

Campsite in Thonotosassa

5 out of 5 average rating, 232 reviews

The Palm Tree Getaway

Top guest favorite

A heated saltwater pool is surrounded by lush tropical landscaping, with clear blue water reflecting the sky above. A colorful float rests on the water's surface. The screened enclosure provides a barrier while allowing for views of the serene outdoor space.

Guest suite in Tarpon Springs

4.96 out of 5 average rating, 130 reviews

Private suite in heart of Tarpon Springs!

A welcoming exterior view of the house, featuring a landscaped front yard with palm trees and decorative rocks. A large driveway leads to a garage, while outdoor seating is visible on a covered porch, framed by large windows and soft natural light.

Home in Palm Harbor

4.99 out of 5 average rating, 140 reviews

Tropical Oasis Retreat w/ Heated Pool

A compact bedroom features a neatly made bed adorned with decorative pillows. A small nightstand with a lamp is positioned beside the bed. Wall art depicting floral designs enhances the room's decor. A fan hangs from the ceiling, providing airflow.

Apartment in Port Richey

4.9 out of 5 average rating, 123 reviews

La Palma

A spacious bedroom features a large bed adorned with a patterned duvet, complemented by a decorative headboard. A flat-screen TV is mounted on the wall opposite, flanked by speakers. A cozy teddy bear is positioned on a chair nearby, and a small space heater adds warmth to the room.

Townhouse in New Port Richey

5 out of 5 average rating, 6 reviews

Beautiful private suite with private entrance

Family-friendly home rentals with a pool

A serene view from the screened lanai highlights a private heated pool, reflecting the soft colors of a sunset. The tranquil waters of the Anclote River can be seen beyond the pool, framed by lush greenery and trees along the riverbank.

Home in Holiday

4.98 out of 5 average rating, 42 reviews

River Home with Pool, Sunset, Dolphin & Fishing

An inviting outdoor space is showcased, featuring a private saltwater pool under a screened enclosure. Sun loungers are positioned beside the pool, with a view of the Anclote River visible through the screening. A 50” TV is mounted nearby for entertainment.

Home in Holiday

4.9 out of 5 average rating, 20 reviews

Waterfront Oasis-Tarpon Sunsets-Pool-Kayak-Fishing

A screened porch is visible, framed by palm trees, overlooking the serene waterfront. The sunset casts a warm glow across the scene, reflecting on the water. Comfortable seating arrangements are positioned on the porch, creating an inviting space to relax and enjoy the view.

Home in Holiday

4.87 out of 5 average rating, 67 reviews

Home with a View and heated pool/ solar panels

Top guest favorite

A fenced solar-heated swimming pool features smooth, blue water. Lounge chairs and a small table are positioned on the surrounding patio, while a floating pool toy and a colorful ball are visible in the water. A laundry drying rack stands beside the pool area.

Home in New Port Richey

4.93 out of 5 average rating, 141 reviews

Mackarosa Tampa Bay Luxury Pool House

A private outdoor heated pool is framed by a concrete patio, featuring a curved design and clear blue water. Four colorful chairs provide seating around the pool, with additional lounge chairs nearby. A wooden fence offers privacy in the background.

Home in Port Richey

4.9 out of 5 average rating, 205 reviews

"Wet Feet Retreat" pool home

An aerial view captures a cozy lakeside home surrounded by lush greenery and palm trees. The screened-in private pool is visible, along with a nearby dock extending into the water. A fire pit area is seen, providing a space for gatherings. Scenic views enhance the outdoor experience.

Home in Holiday

4.91 out of 5 average rating, 86 reviews

Lakefront Paradise with Private Saltwater Pool

Top guest favorite

A spacious, heated saltwater pool is surrounded by a sun patio, showcasing light-colored pavers. Lounge chairs and an umbrella provide shaded seating. The pool has steps for easy entry and is set against a backdrop of wooden fencing and well-maintained grass.

Home in Holiday

4.97 out of 5 average rating, 91 reviews

Private 3 Bedroom House w/ Heated SaltWater Pool

Top guest favorite

A spacious outdoor area reveals a crystal-clear heated pool, surrounded by a screened patio. Comfortable lounge chairs and a dining table with an umbrella enhance the idyllic setting, inviting relaxation. Large glass doors along the back wall provide a view into the home, blending indoor and outdoor experiences.

Home in Tarpon Springs

4.99 out of 5 average rating, 109 reviews

Tropical Pool Retreat in Tarpon Springs

Quick stats about vacation rentals that are family-friendly in Holiday

Total rentals
90 properties
Nightly prices starting at
ﺩ.ﺇ110 before taxes and fees
Total number of reviews
2.7K 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

Destinations to explore