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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, 112 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.

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)

Top guest favorite

A spacious sleeping area features a large bed with a neatly arranged white coverlet. A comfortable sitting area is visible on the side, complemented by a lamp that provides soft lighting. A small window with light-colored curtains adds natural brightness to the room.

Apartment in New Port Richey

5 out of 5 average rating, 106 reviews

Cozy Apt. Suite - Sunny Tampa Bay Area

Don’t be fooled,This is a real gem and remodeled unit. Kick back and relax at this peaceful and cozy suite. Located near Historic Downtown New Port Richey and Trinity Area. You can visit the nearby Tarpon Springs Sponge Docks, Honeymoon Island or Clearwater which is rated one of the top 10 beaches in the nation. We are centrally located near 3 community hospitals. Travel Nurses or Professionals are welcomed. Whether you are traveling for leisure or work this is the place for you!

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

The bedroom features a spacious bed dressed in a floral-patterned coverlet. A small table is placed at the foot of the bed, displaying the word 'RELAX.' A closet is visible beside the bed, and light-colored walls complement the wooden flooring.

Guest suite in Holiday

4.98 out of 5 average rating, 52 reviews

Holiday Sandy

Escape to this cozy private apartment with a separate entrance, just minutes from the beach and Little Greece. Located in a quiet, safe area—perfect for relaxing or working from home. Unwind on the private terrace and enjoy: ✔ Fully equipped kitchen ✔ Bedroom with work desk ✔ Smart TV, WiFi ✔ Spacious bathroom with high-capacity shower ✔ Free parking Ideal for couples or solo travelers seeking peace near the sea.

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, 129 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

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

4.91 out of 5 average rating, 127 reviews

Renovated peaceful 2 Bed cottage with/hot tub.

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, 368 reviews

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

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

An outdoor view showcases a spacious backyard featuring a large heated pool surrounded by palm trees. A pickleball court and a half basketball court are visible, each with distinct colorful surfaces. Various outdoor games and seating options enhance the active environment.

Home in Clearwater

5 out of 5 average rating, 119 reviews

FL Gem ! XL Pool | Pickleball | B-Ball & More!

Top guest favorite

An outdoor porch features a two-person Jacuzzi, inviting relaxation while overlooking a lake. Warm lighting is provided by lanterns, creating an ambient atmosphere against the backdrop of a colorful sunset and silhouettes of trees.

Tiny home in Dade City

4.98 out of 5 average rating, 146 reviews

Eco-Luxurious Lakefront haven (Fire pit & Hot Tub)

Top guest favorite

The porch features a circular daybed with decorative cushions, accompanied by a small table and two chairs. Direct views of the bright blue sky and nearby palm trees are visible, enhancing the outdoor relaxation space.

Cottage in Indian Rocks Beach

4.97 out of 5 average rating, 146 reviews

𖤓Updated Stilt home: just steps to the beach!𖤓

Top guest favorite

The image captures a spacious townhouse community, featuring white architectural designs. A clear view of the intercoastal waterway is presented, with boats visible in the distance. A community pool is seen among vibrant greenery, inviting leisure and relaxation.

Townhouse in Clearwater Beach

4.99 out of 5 average rating, 113 reviews

3 Bedroom Waterfront Paradise Sleeps 8

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 living area displays a comfortable brown couch adorned with soft green cushions, positioned near a rustic wooden coffee table. An open-concept kitchen is visible, featuring modern fixtures and shelving, with a dining area that includes two stools. Natural light filters through a window, enhancing the space.

Home in New Port Richey

4.92 out of 5 average rating, 130 reviews

1 block to dwnt/7min beach/King bed/Free parking

Top guest favorite

A cozy bedroom features a cloud-themed blue wall, complemented by light-colored furniture. The spacious bed is dressed in a cloud-patterned comforter, and a soft, cloud-shaped rug lies on the floor. Natural light enters through the doorway, enhancing the serene atmosphere.

Tiny home in Port Richey

5 out of 5 average rating, 9 reviews

Las nubes

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

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, 131 reviews

Private suite in heart of Tarpon Springs!

Top guest favorite

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

Top guest favorite

A gentle-looking fox rests on the ground beneath a fence, surrounded by greenery. Its white fur blends with the natural surroundings, and its dark eyes reflect curiosity. The area is covered with soft earth and decorative wood chips, creating a tranquil setting.

Farm stay in Dade City

4.92 out of 5 average rating, 339 reviews

Duck Haven - Wildlife Sanctuary - 5 miles to I75

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

Top guest favorite

A spacious covered screened porch features a heated pool visible nearby. Lounge chairs with cushions are arranged beside the pool. A dining table with chairs is positioned on the porch, alongside a propane gas grill, all set against a backdrop of surrounding greenery.

Home in Port Richey

4.99 out of 5 average rating, 243 reviews

Heated & Screened in Pool-All Essentials Provided

The outdoor area features a sparkling pool surrounded by a screened-in patio. Comfortable seating and a dining table are visible beneath a mural depicting a beach scene, while greenery adds a touch of nature. Large windows provide light into the indoor space.

Home in New Port Richey

5 out of 5 average rating, 45 reviews

New Port Richey.Private heated pool(solar panels).

An aerial view presents a Florida-style home with a spacious outdoor area. A circular pool is surrounded by sun loungers, and a pergola is partially shaded by greenery. The yard features well-maintained grass and low landscaping across the enclosed space, adding to the tranquil atmosphere.

Home in Holiday

5 out of 5 average rating, 47 reviews

Florida style home !

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.

Home in Tarpon Springs

4.89 out of 5 average rating, 136 reviews

Game Room, Heated Pool, 5 minutes to Beach

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, 206 reviews

"Wet Feet Retreat" pool home

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, 110 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