Family-friendly holiday rentals in Windsor Hills

4.97 out of 5 average rating, 101 reviews

Disney Pool Villa | Windsor Hills | Sleeps 8

BOOK EARLY! Rated top 1% & Guest Favorite. Our popular home fills up 3-4 months in advance. 3BR/3BA Private Pool Villa in Windsor Hills Resort, Kissimmee! Newly renovated, gated resort, 3 miles to Disney World. Modern beach-coastal design, updated kitchen, family-friendly layout. Free parking, Wi-Fi, full resort access (pool, splash park, gym, playground). Near Universal (20 min), SeaWorld (18 min), Legoland (40 min). Perfect location for vacations Disney trips, sports events, and conventions.

A playful bedroom features twin beds with a colorful 'Aloha' theme. The living area showcases a dining table for six and a comfortable seating arrangement. A screened patio displays a private pool. An entertainment room is equipped with game tables and superhero-themed decor.

5 out of 5 average rating, 23 reviews

Disney Family Fun Villa

Windsor Hills - NEW Fully Renovated 6Bed&4Bath Villa with FREE pool heat - Private South Facing Pool and Spa - Smart TVs in every room - Free WIFI - Fully renovated & equipped kitchen with granite countertops & new appliances - 1.5 Miles to Disney - Close to Universal Studios, Shopping,Restaurants,Waterparks - Gated Community - Free Clubhouse Access with New Waterpark, Basketball, Tennis & Volleyball Courts & Putting Green - Newly renovated Marketplace Bar & Grill, Games Room & Convenience Store

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.

4.99 out of 5 average rating, 149 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.

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.

4.97 out of 5 average rating, 156 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!

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.

4.87 out of 5 average rating, 144 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!

4.98 out of 5 average rating, 121 reviews

Apartment in Kissimmee

11 am checkout, Windsor Hills, Family, Disney.

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.

An engaging game room showcases colorful murals and a variety of arcade games, including basketball and foosball. A vibrant Toy Story-themed bedroom features bunk beds and playful decor, while a view of the private heated pool is presented from the charming living area, surrounded by large windows.

4.93 out of 5 average rating, 43 reviews

Themed villa: Pvt Pool: Near Disney: Gameroom, BBQ

Welcome to The Colorful Cove, a vibrant family getaway near Disney and other top attractions. Enjoy an exceptional experience as you splash in a private pool, play fun games, enjoy outdoor dining and relax in rooms with updated furnitures and amazing themes. Plus, enjoy access to resort amenities including the waterpark, sports courts, fitness center and clubhouse Disney World-8 min drive Old Town-14 min drive Universal Studios-30 min drive Book For Unforgettable Memories In Kissimmee!

A collage of vibrant images showcases the luxurious amenities available, featuring a spacious pool area, themed bedrooms, an arcade room, and outdoor seating. The photos capture a welcoming environment ideal for family gatherings and entertainment, beautifully arranged in a Mickey Mouse shape.

4.99 out of 5 average rating, 104 reviews

Cozy Themed Villa 6 BR | Close to Disney

🏖️☀️🏄‍♀️Stay just minutes from Disney in this spacious 6-bedroom home, perfect for a family getaway. It comfortably sleeps up to 14 guests and is designed for both kids and adults to enjoy. Located in Windsor Hills Resort — one of the closest communities to Disney World — you’ll have quick and easy access to the parks. Enjoy themed bedrooms, a game room, and your own private patio and pool — great for relaxing after a fun day at Disney.🌴👙🩳🥽🩴 ❤️❤️We'd love to welcome you here!

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.

4.96 out of 5 average rating, 158 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

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.

4.99 out of 5 average rating, 247 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.

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.

4.98 out of 5 average rating, 112 reviews

Luxury Villa Windsor Hills Resort 2 miles / Disney

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

A spacious living area features a contemporary design with a large flat-screen TV mounted on the wall, surrounded by comfortable seating. A stylish coffee table is centered on a soft area rug, and decorative plants add a touch of greenery. The bright space is complemented by warm lighting.

4.96 out of 5 average rating, 24 reviews

Hibiscus Villa w/ themed rooms, game room and pool

Welcome to your luxurious single story 4-bedroom getaway in the heart of a gated resort just 2.6 miles from the magic of Disney World! This meticulously designed vacation home offers not only comfort and convenience but also an array of resort amenities that promise an unforgettable stay. Your dream vacation home is not just a place to stay; it's a gateway to a world of enchantment and relaxation. Book your stay now and let the magic begin!

Popular amenities for Windsor Hills family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

5 out of 5 average rating, 17 reviews

The Disney House • Immersive Rooms • Gaming Lounge

5 out of 5 average rating, 9 reviews

Fully themed, free arcade, south facing pool & spa

4.95 out of 5 average rating, 58 reviews

Themed Family Pool Home 10 Min to Disney Game Room

4.95 out of 5 average rating, 39 reviews

The image captures a vibrant outdoor resort area featuring a lagoon-style pool and waterslides in shades of blue and green. Sun loungers are arranged around the pool, surrounded by palm trees and open green spaces. A two-story condo building stands in the background.

Apartment in Kissimmee

Sunny Condo Retreat~Less-Stress|Organized|Clean

5 out of 5 average rating, 46 reviews

Once upon a galaxy: Star Wars/fairytale retreat

The image showcases a colorful game room featuring themed decor, cozy lounging spots, and engaging game tables. A separate view displays a vibrant community water park with palm trees and pool areas. The combined images highlight the fun and relaxation available in the villa's surroundings.

4.9 out of 5 average rating, 68 reviews

ReDesigned | Windsor Hills | Location | Water Park

5 out of 5 average rating, 10 reviews

An elevated stay, a true experience

A vibrant game room features a foosball table as its centerpiece, surrounded by colorful murals of playful characters. A basketball hoop is positioned against a wall with a set of basketballs nearby. An arcade game machine is also visible in the background.

4.91 out of 5 average rating, 32 reviews

FREE Heated Pool | 2mi Disney | 5BR Themed Villa

Family- and pet-friendly home rentals

4.86 out of 5 average rating, 101 reviews

4m Disney Sun, Free Snacks, Golf, Pool• Spa• Games

Superhost

An aerial view displays the community's expansive pool area featuring a water slide and ample lounge chairs under palm trees. The lower images showcase a vibrant living area with comfortable seating, a dining space with bar seating, and a colorful bedroom decorated with Toy Story themes.

Townhouse in Kissimmee

4.84 out of 5 average rating, 128 reviews

Peter Pan's Flight - Disney Themed Townhome

Superhost

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.

4.87 out of 5 average rating, 131 reviews

Disney Escape at Windsor Hills

A vibrant children's bedroom is adorned with a whimsical mural depicting fairytale scenes. Two beds with elegant metal canopies frame the room, each dressed in colorful bedding featuring princess themes. Natural light filters in through a window, complementing the playful decor.

4.95 out of 5 average rating, 172 reviews

🏰 Disney Princess Crownhouse! Closest to Disney!

A themed movie theater room is presented with dark walls and vibrant purple lighting. Comfortable lounge seating is arranged towards a large screen, showcasing a colorful animated scene. Mario-themed decor and graphics adorn the walls, creating an engaging atmosphere for family movie nights.

5 out of 5 average rating, 104 reviews

5BR Mario& Princess Peach•Pool•Theater•Free Resort

The exterior of the home features a spacious driveway, paved in light-colored bricks, leading up to an attached garage with an ornate door. A well-maintained lawn with green grass and palm trees is visible, complemented by a clear blue sky filled with clouds.

4.8 out of 5 average rating, 112 reviews

View the Disney fireworks from your pool!

4.86 out of 5 average rating, 345 reviews

The exterior of the Westgate Vacation Villas showcases an elegantly designed building with multiple levels. Soft lighting from street lamps illuminates the entrance. Rows of golf carts are parked in front, surrounded by manicured landscaping and palm trees under a clear blue sky.

Apartment

Westgate Vacation Villas - 1 Bedroom

4.82 out of 5 average rating, 168 reviews

A screened-in private splash pool is surrounded by comfortable seating, featuring playful Minion characters on the walls of the adjoining rooms. The layout includes vibrant décor and modern furnishings, creating a family-friendly space with direct access to outdoor relaxation.

Townhouse in Kissimmee

Themed Pool Home 2 Miles to Disney

Family-friendly home rentals with a pool

The exterior of a two-story home is shown, featuring a light-colored façade with large windows. A vehicle is parked in the driveway, and green shrubs and a magnolia tree are visible in the well-maintained yard. Clear blue skies provide a bright backdrop.

4.86 out of 5 average rating, 29 reviews

3 Miles from Disney 5/5 Pool home-free pool heat

4.94 out of 5 average rating, 17 reviews

Windsor Hills, Disney/Universal, Pool/SPA, 5BR5BA

A vibrant gaming room features a blend of classic arcade machines and modern gaming consoles. Two large screens display colorful graphics, while two Daytona USA racing machines and various arcade units provide entertainment. A sleek red and black couch offers comfortable seating in this lively space.

4.95 out of 5 average rating, 94 reviews

Ultimate Adventure Villa Top Rated 5 Star Disney m

4.97 out of 5 average rating, 79 reviews

Home mins to Disney, pool, arcade, waterslides

4.97 out of 5 average rating, 59 reviews

A children's suite hosts a whimsical treehouse-themed bunk bed with a slide, shaded by mural-painted trees. Soft green carpet covers the floor, and a plush gray sofa is positioned nearby. A stuffed Winnie the Pooh character adds a playful touch to the setting.

Townhouse in Kissimmee

Free H2O Slides~Disney 4mi~Pvt Pool~2 King Suites

An outdoor seating area features vibrant blue chairs and a shaded patio overlooking a private pool. Surrounded by a screened enclosure, the view includes manicured grass and trees, creating a serene setting for relaxation and enjoyment.

4.89 out of 5 average rating, 18 reviews

Themed Luxury 6BR Getaway with Resort Amenities Pr

A private backyard oasis features a heated pool and hot tub, framed by a screened enclosure. Large sun loungers are placed on the pool deck, offering a relaxing space. The scenic view includes lush greenery with no rear neighbors, ensuring privacy for guests.

4.86 out of 5 average rating, 42 reviews

Family Disney Home | Pool | Game Room | Hot Tub

The image showcases a private pool surrounded by a screened lanai with colorful floatation devices resting on the water's surface. In the background, the open green space and Windsor Hills Resort amenities, including water slides and playgrounds, extend beyond the pool area, offering recreational opportunities.