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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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Guest favorite
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 Timber Oaks
5 out of 5 average rating, 157 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 & "snowbird" guests.

Superhost
A modern bathroom is shown featuring a sleek vanity with a rectangular sink and black fixtures. A round mirror is illuminated by three overhead lights. Storage is provided by wooden drawers beneath the sink, and towels are neatly arranged on shelves.
Guesthouse in Palm Harbor
4.86 out of 5 average rating, 161 reviews

Home away from home

Private unit has designated parking, pool access, its own water heater, water softener, filtration system, 2 ceiling fans, heater, air purifier & a/c. Featuring a queen bed, dresser, 42” tv & fire stick w/ streaming accounts, wifi, full length mirror, recliner, eating table & chairs. The bathroom has a walk-in shower, large vanity mirror, & all the needed bathroom accessories. Full kitchenette w/ microwave, dual burner, air fryer, tea kettle, coffee maker, & more. Owner lives on property.

Guest favorite
A comfortable living space includes a dark blue sofa with accent pillows and a coffee table. A dining area with wooden chairs is visible in the background, alongside a fully equipped kitchen. Light-colored cabinets and appliances complement the space.
Guesthouse in Tarpon Springs
4.85 out of 5 average rating, 103 reviews

Comfy 1BR Near Beaches & Sponge Docks

Enter your private oasis & enjoy our spacious 1 bd in scenic Tarpon Springs. Relax on the comfy couch or oversized chair. Treat yourself to free snacks, cold water & coffee, tea or hot cocoa w/ the Keurig in the fully equipped kitchen! Enjoy a hot shower or bath. Extra toiletries supplied. Games & books available. Comfortable Queen size bed ensures a great sleep. Only 3 miles from Howard Park Beach & Sponge Docks. Sunset Beach 1.3 miles. Innisbrook Golf Resort 3.9 miles! Private Entrance

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, 258 reviews

Heated & Screened in Pool-All Essentials Provided

🏡 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.

Guest favorite
An outdoor seating area is sheltered by a wooden pergola adorned with string lights. A cozy couch is positioned on a decorative area rug, complemented by a small table. Lush greenery surrounds the space, providing a tranquil environment for relaxation.
Guesthouse in Dunedin
4.84 out of 5 average rating, 126 reviews

Guest House in prime location!

This special place is close to everything, making it easy to plan your visit. Less than 30 minutes to TPA Airport, 13 miles to Clearwater Beach, 2.2 Miles to Honeymoon Island, 1.0 miles to US-19 to easily get to surrounding areas, and 3.5 miles to downtown Dunedin. Guest house located on property with friendly host. There is one parking space provided for guests onsite. Happy to provide recommendations for a local experience during your stay! Beach necessities available upon request.

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, 134 reviews

Private pool suite in heart of Tarpon Springs!

Charming private suite in a safe, serene neighborhood—just minutes from beaches, Downtown Tarpon, Sponge Docks & Sunset Beach! Your cozy retreat features a private entrance, queen bed, fast WiFi, cable television, a full kitchen & heated in-ground pool. Explore Tarpon Springs and the Pinellas Trail on provided bikes, then unwind at Sunset Beach with provided beach towels, chairs, umbrellas, toys, cooler & sunscreen. This space is a perfect blend of comfort, convenience & coastal charm!

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, 108 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!

Guest favorite
A private swimming pool is surrounded by a screened patio, with colorful floatation devices resting on the clear water. Lounge chairs are positioned nearby against a bright yellow wall. Natural light floods the area through glass doors, creating a refreshing atmosphere.
Home in Forest Hills
4.91 out of 5 average rating, 121 reviews

Heated Pool Oasis • 5mi Tarpon & Beaches

Oasis with a private pool heated Nov–Mar and a patio, 5 miles from Tarpon Springs, near Dunedin and a short drive to Clearwater/Tampa. Perfect for family or friends: fast Wi-Fi, workspace, fully equipped kitchen, and BBQ. 24/7 self check-in and on-site parking. Quiet for restful nights; beaches and parks minutes away. Note: pool heating available November–March (weather-dependent). Last-minute promos active. Book today!

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, 188 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.

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
4.97 out of 5 average rating, 138 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.

Guest favorite
A spacious sleeping area is highlighted by a wooden bed frame adorned with a light-colored quilt featuring floral patterns. A small writing desk and chair are positioned near the window, while a sliding wooden door leads to an en-suite bathroom.
Place to stay in New Port Richey
4.94 out of 5 average rating, 177 reviews

Sunflower Studio

Here you wake up to birdsong, as we are in the middle of a bird sanctuary. A peaceful place in the middle of a busy city. Sunflower Studio is a unique experience that you must feel. It will be a pleasure to welcome you, make your reservation!

Popular amenities for Holiday family-friendly rentals

When is the best time to visit Holiday?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ514ﺩ.ﺇ540ﺩ.ﺇ584ﺩ.ﺇ558ﺩ.ﺇ488ﺩ.ﺇ540ﺩ.ﺇ518ﺩ.ﺇ488ﺩ.ﺇ459ﺩ.ﺇ510ﺩ.ﺇ488ﺩ.ﺇ507
Avg. temp17°C18°C20°C23°C26°C28°C29°C29°C28°C25°C21°C18°C

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

  • Total vacation rentals

    Explore 90 vacation rentals in Holiday

  • Nightly prices starting at

    Holiday vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

  • Verified guest reviews

    Over 2,780 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    80 of Holiday vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Holiday rentals

  • 4.7 Average rating

    Holiday stays receive an average rating of 4.7 out of 5 from guests