Family-friendly holiday rentals in Windsor Hills

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Windsor Hills

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite
The spacious living area features comfortable seating arrangements, large windows, and a decorative area rug. The view leads to the private screened-in pool, providing a seamless indoor-outdoor experience. The room is illuminated by natural light and complemented by a modern ceiling fan.
Home in Kissimmee
4.99 out of 5 average rating, 142 reviews

Game & Theater Room, Castle Bunks, Pool & Spa

Vacation at Windsor’s Best located in Windsor Hills Resort just 2 miles from Walt Disney World. This one-story 4 bed, 4 bath vacation villa has everything you need for a wonderful getaway with family or friends. Situated on an elevated corner lot, this spacious villa with it's private pool and spillover spa offers a beautiful view overlooking the resort community. Plus, guests have access to the family-friendly Windsor Hills Resort amenities, including the water park, playgrounds, gym and more.

Top guest favourite
A modern kitchen features stainless steel appliances, bright white cabinets, and a clean countertop. In the background, large windows provide a view of the outdoor space. The cozy living area showcases a comfortable seating arrangement and tropical-themed decor, with light streaming through the glass doors.
Townhouse in Kissimmee
4.94 out of 5 average rating, 193 reviews

5 miles to Disney- Private Pool - Arcade Games

Just 4 miles from Disney, our luxury townhome is your family’s perfect escape! With a private splash pool, brand-new 65ā€ Smart TV, and family-friendly gear (stroller, pack n’ play, high chair), you’ll have everything needed for a carefree stay. Located across from Windsor Hills Resort’s clubhouse, enjoy resort perks like a pool, splash pad, fitness center, and theater! Sleeps 8 comfortably with 3 en-suite bedrooms, including a themed Disney beach kids’ room. Fun, comfort, and convenience await!

Guest favourite
A colorful kids' retreat features vibrant, themed wall art depicting racing characters against a bright, rainbow backdrop. A flat-screen TV is mounted on the wall, and a multi-drawer storage unit is positioned nearby. The room is designed to inspire imagination and enjoyment.
Townhouse in Kissimmee
4.95 out of 5 average rating, 112 reviews

*NEW*FREEwtrprk/5mins2disney/3Bdm/freebreakfast

Before exploring your vacation home- please click the heart and save us as a favorite!! This truly does help us be seen and is greatly appreciated. Plus, you can always find us when you are ready to book :) check out our website theprimrosewh and find us on IG MINUTES to DISNEY WORLD & US 192 with lots of restaurants/shops/walmart 1min. NEWLY renovated BRIGHT & VIBRANT 3 bed, 3 bath END UNIT townhome with private pool in the popular WINDSOR HILLS Closest townhome to the CLUBHOUSE steps away

Top guest favourite
An outdoor dining area features a large, custom-built wooden table surrounded by black chairs. Blue plates and glassware are meticulously arranged for an inviting meal. A bright blue pool glimmers in the background, enclosed by a mesh screen to ensure privacy.
Villa in Kissimmee
4.97 out of 5 average rating, 143 reviews

*Brand New!* Minutes to Disney + Free Resort!

Closest FREE resort to Disney Parks! Hibiscus Hideaway is a 6 bedroom 4 bathroom luxury villa that sleeps 14. Completely renovated in October 2022! * Kitchen is loaded & all baby gear provided. * Custom game room with A/C, LED panel lighting & ROCK CLIMBING WALL! * New Roku smart TVs & NEST tech throughout. * Outdoor space includes your own private pool, hot tub, overhead lighting, NEW BBQ grill & 10' custom-built farmhouse table to seat the whole family! Every detail has been thought of!

Superhost
The image showcases a vibrant family-friendly condo, featuring colorful Disney-themed decor throughout the open living space. A spacious pool area is visible beyond the window, highlighting water features and play areas, while the cozy sleeping area is highlighted in the foreground.
Apartment in Kissimmee
4.85 out of 5 average rating, 155 reviews

Toy Story Retreat Near Disney in Windsor Hills

Experience the magic of Disney at your very own ā€œToy Story Retreat.ā€ - 3 bedrooms and 2 bathrooms with Disney-inspired design - Family-friendly atmosphere in a newly remodeled condo - Full access to Windsor Hills Clubhouse amenities - Ground-floor unit with greenspace views - Free WiFi and basic cable included - Just minutes from Walt Disney WorldĀ® Resort It's important that the title is as close to 50 characters. You should use some of the other characteristics of the listing.

Guest favourite
Townhouse in Kissimmee
4.94 out of 5 average rating, 141 reviews

Mickey's Dream: Free Waterpark, 10min to Disney!

This Mickey-themed 3-bedroom, 3-bath townhouse is located just 10minutes from the Disney gate in the popular & secure Windsor Hills Resort. Amenities include: FREE WATER PARK and SPLASH PAD, pool, playgrounds, fitness center, arcade and more! Screened in back patio complete with private splash pool. Open concept main floor includes space for enjoying a movie night or eating dinner as a family. Living room and 3 bedrooms come with Smart TVs for streaming. Hi-speed WiFi, cable TV. Washer/Dryer

Guest favourite
The exterior of the house is showcased, featuring a two-story design with light-colored walls and a prominent entrance. A spacious driveway accommodates up to four vehicles, bordered by well-maintained green lawns and trees. The property is set within a landscaped community.
Home in Kissimmee
4.97 out of 5 average rating, 145 reviews

Highest Rated Minutes to Disney! -Newly Renovated

• Newest house in the #1 community in the Disney Area, Windsor Hills • Only home with 7 bedrooms in the community (3 KING beds) • Extra privacy: only one side & no rear neighbors • 4 children themed bedrooms (Mickey, Star Wars, Toy Story, & Frozen) • Onsite, driveway parking for 4 vehicles • FREE pool heat + BBQ with all rentals • Fully equipped + stocked kitchen • Self check-in with digital lock • Super FAST Wi-Fi wireless internet speed at +1000 Mbps • Property is managed directly by owner

Guest favourite
A light-filled living area features a gray sectional sofa with accent pillows, arranged around a low coffee table. A patterned rug sits beneath, while a tall floor lamp adds warmth. Large sliding glass doors provide views of the outdoor patio, framed by sheer curtains.
Townhouse in Kissimmee
4.96 out of 5 average rating, 108 reviews

Star Wars Bungalow | 4 Mi to Disney | Waterpark

Enjoy your stay at this gorgeous, freshly renovated home! MINUTES to Walt Disney World. • šŸŽ¢ WATER SLIDES • 🌟THEMED Star Wars Retreat ā€¢šŸ“ Entertainer's Kitchen • 🤱 BOB Jogger Stroller available • šŸ–ļø Private patio with HEATED POOL • ā˜•ļø **Latte and Coffee Bar** • šŸ“¶ Fiber High Speed Wi-Fi Thoughtfully curated for your ultimate ENJOYMENT. Beautiful modern interior, ceramic tile floors, and high quality decor throughout. This impeccable 3 bedroom, 3 bath home sleeps up to 8.

Top guest favourite
A vibrant games room is equipped with various arcade machines, including SpongeBob Racing. A massage chair is positioned nearby, while a theater room features plush seating. An outdoor space highlights a screened-in pool area surrounded by palm trees, visible through large windows.
Home in Kissimmee
5 out of 5 average rating, 241 reviews

Windsor Orlando Private Arcades,Theater,Pool-Spa

Orlando, Disney, Arcade, Movie Theater, Massage Chair, Pool, Hot Tub, 2 King Beds, Kids Bunk Bed, Kissimmee. Upgraded games room IN the private home, theater for evenings home and your private lanai with pool and hot tub. Choose from including Pump It Up dance, Sponge Bob Racing, NASCAR racing, Legends 3, Pac-Man's Arcade Party, an 80-inch TV, and an Xbox 360. Watch your favorite movies on the 92-Inch projection screen, surround sound, and stadium style seating.

Top guest favourite
An overview of luxury amenities includes a vibrant water park with slides, a spacious pool surrounded by palm trees, and a modern game room featuring foosball and striking wall art. Nearby, a tranquil bedroom setup and an inviting private pool are also highlighted.
Villa in Kissimmee
4.98 out of 5 average rating, 104 reviews

Luxury Villa in Windsor Hills Resort, 2 miles / 5

4 bed and 4 bath LUXURY VILLA located in the top rated WINDSOR HILLS RESORT, just 2 MILES / 5 MINUTES AWAY from Walt Disney World This Villa is newly renovated, immaculately clean, and has all you need for a fun and comfortable vacation. The Villa offers the ultimate game room, outdoor dinning, and a screened private pool & spa. All guests also have access to resort amenities. Lots of entertainment for all. * Security Deposit Required with reservation

Guest favourite
A private pool area is enclosed by a protective screen, providing a serene oasis. The pool is surrounded by tiled flooring, with a table and chairs nearby for relaxation. Bright curtains frame the entrance to the living space, enhancing the overall inviting atmosphere.
Townhouse in Kissimmee
4.91 out of 5 average rating, 243 reviews

DISNEY, WATER park, Private POOL, Comfort by A3G

Your dream getaway, starts In this 3beds 3 baths vacation home away from home! With private pool, Located in the amazing 5 stars resort at WINDSOR HILLS, only 3 miles away from all the wonders and magic of Disney. For Endless entertainment just walk to the Clubhouse and encounter the beautiful typhoon style pool, jacuzzi, brand new water park, arcade, fitness center, volleyball and basquetbol courts, kids playground and much more

Top guest favourite
Home in Kissimmee
4.97 out of 5 average rating, 121 reviews

3BD/3BA Themed House Near Disney

Welcome to our charming 3-bedroom, 3-bathroom house, thoughtfully created to create magical moments for your entire family! Immerse yourself in our themed rooms, each capturing the magic of beloved stories like Happy Potter and Mickey Mouse. Accommodating up to 10 guests, your Disney adventure starts here! The following extra services include additional costs: Grill Early Check-in Late Check-out

Popular amenities for Windsor Hills family-friendly rentals

When is the best time to visit Windsor Hills?

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Avg. price$298 SGD$301 SGD$323 SGD$328 SGD$289 SGD$298 SGD$318 SGD$288 SGD$262 SGD$294 SGD$302 SGD$334 SGD
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Quick stats about holiday rentals that are family-friendly in Windsor Hills

  • Total holiday rentals

    Explore 620 holiday rentals in Windsor Hills

  • Nightly prices starting at

    Windsor Hills holiday rentals start at $90Ā SGD per night before taxes and fees

  • Verified guest reviews

    Over 12,680 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    610 properties feature pools

  • Rentals with dedicated workspaces

    360 properties have a dedicated workspace

  • Wifi availability

    590 of Windsor Hills holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Windsor Hills rentals

  • 4.7 Average rating

    Windsor Hills stays receive an average rating of 4.7 out of 5 from guests

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