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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Guest favourite
Home in Kissimmee
4.76 out of 5 average rating, 133 reviews

No Airbnb fees! Home Theater! Pvt Pool/ Spa 278291

Unable to book this house? Don't worry! Feel free to check my profile for similar homes that might suit your needs WE HAVE 24/7 CUSTOMER SERVICE Disney is just a short 8-mile drive away Tired of visiting the parks every day? Step inside this beautiful thematic 2,169 sqft house with a private pool, spa, BBQ, Star Wars themed movie theater, and a Mario Kart game room complete with arcades, pool table and foosball table all designed for family enjoyment! Make your vacation truly unforgettable!

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, 145 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.

Guest favourite
A townhouse exterior is shown beneath a gentle rainbow. Flanking palm trees provide a tropical setting, while the structure features multiple windows with white frames and dark shutters. A parked vehicle can be seen in front, enhancing the suburban feel.
Home in Kissimmee
4.88 out of 5 average rating, 124 reviews

Disney Escape at Windsor Hills

This is a fantastic family vacation townhouse located just four miles from Walt Disney World! Inside, you'll find a full kitchen with a breakfast bar, a dining table for six, and a living area with a TV for streaming all your favorite channels! Right outside, take a refreshing swim in your private pool. Guests will be able to enjoy a wide variety of resort-style amenities close by including a community clubhouse with a game room, Olympic-size pool, children's waterpark, putting green, 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, 195 reviews

Private Pool & Arcade | Family Disney Townhome

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!

Top guest favourite
A vibrant water park area features colorful slides and splash pads. Water sprays from various playful fixtures, and guests can be seen enjoying the amenities. The backdrop includes a multi-story building with palm trees surrounding the area, providing a fun and engaging environment.
Flat in Kissimmee
4.94 out of 5 average rating, 102 reviews

Newly Renovated Condo! 1.5 miles from Disney World

Make your next trip to Florida one to remember when you stay at our NEWLY RENOVATED 3 bedroom, 2 bath condo located at the Gated Resort Community of Windsor Hills, Four Corners. Just miles from Walt Disney World, Universal studios, Downtown districts, Shopping, golfing and many Restaurants, Windsor Hills has many resort's amenities that are perfect for the family vacation. Our condo grants access to an array of amazing amenities – water park, large pool, arcade room, movie theater and more!!

Top guest favourite
Townhouse in Kissimmee
4.99 out of 5 average rating, 104 reviews

Luxury Mickey Themed Townhome in Windsor Hills Res

3 bed and 3 bath LUXURY Mickey themed townhome located in the top rated WINDSOR HILLS RESORT, just 2 MILES / 5 MINUTES AWAY from Walt Disney World This Mickey themed townhome is newly renovated, immaculately clean, and has all you need for a fun and comfortable vacation. The townhome offers the a screened private pool with pool fence and pool alarm for safety. All guests also have access to resort amenities including new waterpark. Lots of entertainment for all. * Security Deposit Require

Top guest favourite
A home theater room is equipped with red stadium seating for eight, positioned toward a large screen displaying vibrant visuals. An arcade game machine is set beside the screen, with ambient blue lighting accentuating the dark walls, creating an engaging entertainment space.
Home in Kissimmee
4.86 out of 5 average rating, 138 reviews

Resort Home 3.5 miles to Disney with home theater

We welcome you to stay in our home located in the Windsor Hills community with a water park, slides, theatre and so much more! The house is just 3.5 miles from Disney’s Animal Kingdom. Our home has 6 large bedrooms including laundry in the home, an 8 seat home theatre, TVs in every room, a large swimming pool & spa with a large patio cover, plus a large kitchen fully equipped with everything you need for your stay. Please message us if you have any questions, we look forward to hosting you!

Guest favourite
The aerial view showcases a spacious pool area surrounded by lush palm trees and lounge chairs. A bright water slide is visible in the background, leading to the pool. A serene lake serves as a picturesque backdrop, enhancing the resort's atmosphere.
Apartment in Kissimmee
4.85 out of 5 average rating, 203 reviews

One in a Minion condo your kids will love +450Mbps

Enjoy of sophisticated and modern accommodations on your next visit to Orlando. This One in a Minion themed two bedroom condo boasts 1082 SQ FT of living space and it's fully equipped for 6 guests. Conveniently located on the ground floor and a short stroll to the clubhouse, pool and dueling water slides. It features a smart lock, High-speed WIFI Internet +450Mbps, cable TV, telephone line, linens & towels and washer/dryer. Slide and Water Park will not reopen until Wednesday, February 18th.

Top guest favourite
An outdoor dining area features a large blue farmhouse table surrounded by matching turquoise chairs. The setting includes tableware arranged neatly, with the private pool visible in the background. A grill and greenery are also present, providing a relaxed atmosphere for outdoor meals.
Villa in Kissimmee
4.94 out of 5 average rating, 145 reviews

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

Closest FREE resort to Disney Parks! We've named it "Coral Cove" - a 6 bedroom 4 bathroom luxury villa that sleeps 14. Completely renovated in Dec 22! * Kitchen is loaded, & all baby gear provided. * Custom game room with A/C, LED panel lighting & ROCK CLIMBING WALL! *Outdoor space includes your own private pool, hot tub, overhead lighting, NEW BBQ grill & 10' custom-built farmhouse table to seat the whole family! *New Roku smart TVs & NEST tech! *Every detail has been thought of!

Guest favourite
A modern digital door lock is mounted on a light-colored door, featuring a keypad for secure access. A blurred plant with lush green leaves is visible in the background, adding a touch of nature to the entryway.
Guest suite in Kissimmee
4.95 out of 5 average rating, 175 reviews

It's too much like a elegant mini-hotel (5)

It's too much like a elegant mini hotel with rich artistic atmosphere! All the pictures on this page are a reflection of the real condition of the house. All the furniture has been carefully selected, and comfortable mattress and pillows will quickly accompany you into sweet dreams. The biggest feature of this house are comfort, economy and convenience. All of my houses have hosted countless guests from South America, including Brazil and Argentina. You will always be welcome here!

Top guest favourite
A recreational game room is presented, featuring an air hockey table and a pool table centered in the space. Two gaming chairs are positioned near flat-screen monitors on the wall. Colorful LED lighting creates an engaging atmosphere in the room.
Villa in Kissimmee
4.96 out of 5 average rating, 153 reviews

Mr. Clean's Cozy Disney Home w/ Luxury Finishes

• Newest house in the #1 resort community in the Disney Area, Windsor Hills • ALL Mattresses & Pillows are encased in waterproof SANITIZED covers. • 2 FUN children themed rooms (Star Wars, & Frozen) • Onsite, driveway parking for 3 vehicles • FREE pool heat + BBQ with ALL rentals • Fully equipped + stocked kitchen; including Keurig machine • Self check-in with digital lock • Super FAST Wi-Fi wireless internet speed at +1,000 Mbps!! • Property is managed directly by owner

Top guest favourite
A collage showcases various areas of Mickey's Star Wars Retreat. A spacious bedroom features a king-sized bed with blue accents. In another scene, a bright water park is viewed from above. An open kitchen with modern stools, a child's room with themed decor, and a cozy living area with a sectional sofa complete the visual narrative.
Townhouse in Kissimmee
4.98 out of 5 average rating, 106 reviews

StarWars Theme + Free Waterpark | 10 min to Disney

Family-friendly Star Wars Retreat in Windsor Hills Resort — just 10 minutes from Walt Disney World! Enjoy a private screened splash pool, smart TVs in every room, fully equipped kitchen with fun themed touches, and FREE access to resort waterpark, lagoon pool, hot tub, arcade, playgrounds, and sports courts. Washer/Dryer in the home. Spacious, modern, and perfect for multigenerational stays or longer vacations.

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 590 holiday rentals in Windsor Hills

  • Nightly prices starting at

    Windsor Hills holiday rentals start at £52 per night before taxes and fees

  • Verified guest reviews

    Over 13,180 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    580 properties feature pools

  • Rentals with dedicated workspaces

    350 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