Family-friendly holiday rentals in Windsor Hills

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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, 194 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 65” 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
4.94 out of 5 average rating, 113 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!

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, 147 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

Top guest favourite
Apartment in Kissimmee
4.98 out of 5 average rating, 112 reviews

Family, Disney, Windsor Hills, 11 am checkout.

Walk into your home away from home. Enjoy a relaxing stay. Located on 4th floor. Enjoy morning coffee on a screened-in balcony or a late snack. Pet-free home. Please NO Smoking. Children are always welcome. Come enjoy all of the accommodating facilities at Windsor Hills with a top-notched 24/7 gated security. FREE parking & leisure activities! Maximum of 3 cars allowed per reservation. This includes all guest that are visiting. All unregistered drivers will be denied access by HOA.

Top guest favourite
An inviting living space features a modern gray sofa centered around a round coffee table, set on a plush area rug adorned with a playful pattern. A wall-mounted fan circulates air beneath a vibrant Mickey Mouse artwork, while a dining table for four is positioned nearby.
Apartment in Kissimmee
4.94 out of 5 average rating, 170 reviews

🏖 Resort Condo | 🎢 2mi -> Disney | 💦 Waterpark Fun

Welcome to Mickasita @ Windsor Hill's! Our condo is the ideal family vacation spot, conveniently located just minutes away from Disney World and all your desired attractions. During your stay, our whole-condo dehumidifier will maintain a comfortable and healthy level of humidity. Recently upgraded, our condo is sparkling clean and offers many resort amenities with the convenience of a home. You'll find new beds with fresh linens, flat-screen TVs, high-speed internet, a gym, and more.

Guest favourite
An aerial view showcases a resort-style pool surrounded by lounge chairs. A colorful water park with slides is located nearby, complemented by lush greenery and palm trees. Multiple buildings are visible in the background, offering a welcoming atmosphere for families.
Apartment in Kissimmee
4.85 out of 5 average rating, 185 reviews

WH Condo. Pool/Waterpark and close to Disney!

Take an elevator to unit 302 and witness beautifully decorated Disney themed rooms. Directly outside is a lovely pool and kid-friendly waterpark. All amenities included in cost: game room, theater, exercise room, tennis courts, play grounds, sand volleyball, putting green, basketball court and a marketplace and grill. Located 15 minutes to all 4 Disney parks and Sea World! Looking for more space? Check out our townhome also located in Windsor Hills at 7668 Fitzclarence

Guest favourite
Townhouse in Kissimmee
4.93 out of 5 average rating, 165 reviews

Windsor Hills townhouse w/ pool & game room

Welcome to your Disney-area home base - perfect for families and fun-filled stays just minutes from the parks. Enjoy space to relax, play, and recharge in a resort setting designed for all ages: - Sleeps 7 | 3 bedrooms | 4 beds | 3 baths - Private heated splash pool - open all year - Mickey-themed kids’ room w/ Xbox Series X - Free resort access - pool, hot tub & movie theater - Fast wifi, kitchen & in-unit washer/dryer - Family-friendly w/ crib, high chair & strollers

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.

Guest favourite
A queen bed with white linens is centered in this room, complemented by matching nightstands and lamps. Behind the bed, a large mural depicts a castle under a starry sky. A mirror reflects the room's decor, adding to the bright and open atmosphere.
Townhouse in Kissimmee
4.96 out of 5 average rating, 176 reviews

Mickey Pool • Frozen • Waterpark • Near Disney

✨ Step into the magic at our 3-bedroom Windsor Hills townhome — one of the closest gated resorts to the Disney Parks. Enjoy your private heated Mickey pool, an immersive Frozen-themed bedroom, and four Smart TVs for relaxing after park days. Take a break from the crowds with access to Windsor Hills’ resort pool, hot tubs, water park, movie theater, playgrounds, and more. A fun, comfortable home base for families and friends visiting Disney. ✨

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

Popular amenities for Windsor Hills family-friendly rentals

When is the best time to visit Windsor Hills?

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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 € 60 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