Family-friendly vacation rentals in Holiday

Find and book unique family-friendly homes on Airbnb

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

  • Total vacation rentals

    Explore 110 vacation rentals in Holiday

  • Nightly prices starting at

    Holiday vacation rentals start at G$4,185 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,970 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 80 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    110 of Holiday vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Holiday rentals

  • 4.6 Average rating

    Holiday stays receive an average rating of 4.6 out of 5 from guests

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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Top guest favorite
Apartment in Port Richey
4.99 out of 5 average rating, 300 reviews

The Bohemian Studio: Separate Entry & Fenced Patio

🚨Summer & Weekly Discount Serene Countryside Escape. Surrounded by nature & near everything This cozy studio offers total privacy, separate entrance & self check-in Great location, minutes away from hospitals, restaurants, springs & beaches 30 min from Tampa Bay Area 🌳 2 Acres & your own fenced Patio 🍳 Fully Equipped Kitchen & bathroom 💻 High-Speed Internet, Ethernet & FREE Netflix 🚗 FREE Parkings Perfect for traveling workers, visiting family or romantic escapes The best of both worlds!

FamilyKitchenDecor

Guest favorite
A comfortable living area features a beige sofa adorned with orange accent pillows, flanked by two stylish lamps. A round wooden coffee table is positioned on a decorative rug, with modern wall art enhancing the space. A red armchair adds a pop of color to the setting.
Home in New Port Richey
4.9 out of 5 average rating, 117 reviews

Cozy 3-bed home close to beautiful beaches.

Newly updated 3-bedroom, 2-bath home close to everything. Centrally located, within 20-30 mins to the famous Tarpon Springs Sponge Docks, Sunset, Howard Park, Honeymoon Island, Anclote River Park & Clearwater Beaches, Busch Gardens Theme Park and Weeki Wachee. Close toTampa International Airport. Numerous country club golf courses, waterfront restaurants/bars within a short drive. Enjoy your home away from home with everything you need and more with a BBQ Grill/ Fire pit and other amenities.

Indoor spacesKitchenLaundry

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, 170 reviews

Coastal Escape: Heated Pool, Playground&Family fun

★ Family-friendly Palm Harbor retreat near beautiful beaches - Honeymoon Island: 6 miles away - Clearwater Beach: 15 miles away ★ Heated saltwater pool ★ Screened-in lanai ★ BBQ grill ★ Large fenced backyard with playground ★ Outdoor dining area ★ 3 bedrooms with new mattresses - California king size bed - Queen size bed - Kid-friendly room w/ 2 bunk beds ★ Renovated kitchen and bathrooms ★ Open living space for family gatherings and movie nights ★ Toys, games and kid-friendly extras

Indoor spacesFamilyPool

Top guest favorite
A tranquil poolside view captures the serene waters of the Anclote River at sunset. Soft purple lighting reflects from the pool's surface. Spacious seating areas invite relaxation, with silhouettes of boats visible in the background against the vibrant sky.
Home in Holiday
4.96 out of 5 average rating, 108 reviews

Paradise!Renovated waterfront pool home.Sunsets!

No hurricane damage!Sunsets to die for! Completely remodeled in 2023 pool house on the Anclote River with access to the Gulf of America.Imagine fishing,kayaking in the backyard &sometimes you can spot dolphins!Watch birds, ducks, manatees. All new appliances and granite countertops.New quartz bathroom cabinets!New tiles throughout the house including Florida room. Cooler,chairs&umbrella, kids beach toys that you can take to the beach.Bonfire pit.Grill.Heated pool for a fee. Come,relax&enjoy

Indoor spacesKitchenCondition

Top guest favorite
Home in Port Richey
4.99 out of 5 average rating, 290 reviews

Heated & Screened in Pool/Coffee Bar/Fully Stocked

🏡 Private Pool House with Large Covered & Screened-In Porch Relax and unwind in this inviting private pool home, featuring a large covered and screened-in porch—perfect for enjoying the outdoors without the bugs. 🌊 Heated Pool Take a dip in the private pool, heated year-round with an electric heat pump (weather permitting), offering comfort no matter the season. Whether you're sipping coffee on the porch or enjoying a swim, this cozy retreat is ideal for a peaceful and private getaway.

KitchenFamilyAccess

Superhost
Home in New Port Richey
4.89 out of 5 average rating, 108 reviews

River Side Home. Three mins to Downtown.

Cozy apartment for family vacations completely renovated, The SIDE RIVER HOME is very close to downtown, restaurants, bars, boat ramp and walking park overlooking the river, beaches, a few miles from Tarpon Spring Sponge Docks , located 20 mins from Fred Howard Park, if you want to kayak and Canoe the perfect place is Weeki Wachee, just 35 minutes from the house , clearwater beaches are for 42 mins, ahh if the passion is the parks we have Busch Gardens only 52 mins away . PETS ARE WELCOME!

Indoor spacesKitchenSleep quality

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, 210 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)

Indoor spacesKitchenWifi

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
4.95 out of 5 average rating, 385 reviews

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

This home is ideally located near Florida's beautiful Sunset Beach and Howard Park Beach - only 17 miles from Clearwater Beach. Take a short ride to world famous attractions like Disney, or Busch Gardens. Don't settle for a hotel when you and your guests can enjoy a home with a gas grill, multiple patios, large kitchen/family room, a large 4K TV and a private jacuzzi/pool with gas heater *option. It's a perfect place for creating family memories or getting together with old friends.

KitchenFamilyGetting around

Guest favorite
Apartment in Holiday
4.86 out of 5 average rating, 166 reviews

Warmth In Holiday

Tiny Living In Holiday offers a delightful and peaceful ambiance, ideal for a serene getaway. Conveniently located near stunning beaches, guests can revel in the beauty of the coast. The room creates a warm and homely atmosphere, ensuring guests feel snug and content during their stay. Furthermore, the room features a handy air fryer microwave oven combo, allowing guests to effortlessly prepare meals at their convenience. Listing does not accommodate infants/toddlers.

KitchenIndoor spacesHot tub

Guest favorite
Guest suite in Holiday
4.96 out of 5 average rating, 114 reviews

HolidaySpring|CozyPrivate Apt near beach|2 parking

Private & cozy apartment with independent entrance and free parking for two vehicles. Located in a quiet and safe area just minutes from the beach and Tarpon Springs (“Little Greece”) and just minutes from Fred Howard Park Beach.Enjoy a fully equipped kitchen, comfortable bedroom with work desk, Smart TV, fast WiFi, spacious bathroom, and outdoor terrace. Perfect for couples, small families, or remote workers Scan the QR in the last photo for a full video tour

Indoor spacesKitchenAccess

Top guest favorite
Apartment in Holiday
4.98 out of 5 average rating, 114 reviews

Lake access studio near Tarpon Springs.

🌿 Wake up just steps from a peaceful lake and enjoy a stay designed for relaxation, remote work, or exploring Florida's Gulf Coast. This private studio for 2 features a queen bed, fast WiFi, a dedicated workspace, a fully equipped kitchen, private parking, and 24/7 self check-in. Minutes from Fred Howard Park, Sunset Beach, Tarpon Springs, Dunedin, Clearwater, restaurants, and shops. Your perfect escape starts here.

Indoor spacesFamilySleep quality

Guest favorite
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
4.92 out of 5 average rating, 120 reviews

Lakefront Paradise with Heated Saltwater Pool

Discover lakeside bliss at this 2-bedroom retreat with a private pool, dock, and outdoor fire pit. Enjoy stunning waterfront views, relax by the pool, or gather around the fire under the stars. The bedrooms offer a cozy haven, and the fully equipped kitchen ensures convenience. Just minutes from pristine beaches, this retreat provides the ideal balance of relaxation and recreation. Your perfect lakefront getaway awaits!

FamilyIndoor spacesQuiet

Popular amenities for Holiday family-friendly rentals

When is the best time to visit Holiday?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$27,828 GYDG$33,059 GYDG$37,453 GYDG$33,896 GYDG$27,828 GYDG$28,456 GYDG$29,502 GYDG$27,828 GYDG$26,154 GYDG$25,945 GYDG$27,410 GYDG$29,920 GYD
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