House holiday rentals in Windsor Hills

4.97 out of 5 average rating, 102 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

An expansive game room features themed decor, including a vibrant mural of a surfboarder. The private pool area, enclosed with a screen, showcases a clear blue water surface surrounded by spacious lounge chairs. Aerial views of the community pool and water park amenities are also visible.

4.83 out of 5 average rating, 143 reviews

Magical Adv 5 Star Villa Movie Room Arcade Pool an

Experience enchantment at Magical Adventure Villa, a top-rated 6-bedroom and 4-bath home for 12 guests. Conveniently located in Windsor Hills Resort, just 2 miles from Disney World®. Experience the highly acclaimed getaway that has garnered rave reviews. Enjoy a private pool, home theater, and a thrilling arcade. Unleash your inner Jedi at the state-of-the-art Star Wars gaming center with a movie theater, Xbox One, Nintendo Switch, and immersive 3D designs. *Work vehicles are not permitted to b

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.

A spacious living area is seen, featuring a large sectional sofa adorned with decorative pillows. Natural light enters through expansive glass doors, providing a view of the backyard and pool area. Elegant light fixtures hang from the ceiling, complementing the neutral color palette.

5 out of 5 average rating, 109 reviews

Cinderella's HolidayVilla-Minutes from Disney-NEW!

• 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 FULLY REMODELED in Sept 2022!

The living room features a playful Disney-themed design with a comfortable sectional sofa and an entertainment unit. A light-filled bedroom showcases a large bed with subtle Disney accents. The kitchen is equipped with modern appliances, and a dining area presents seating for multiple guests. A bird's-eye view reveals a sparkling pool area surrounded by lounge chairs.

4.97 out of 5 average rating, 100 reviews

NEW Stunning Villa located 5-10 Min from Disney

Welcome to this BRAND-NEW dreamscape Vacation Villa with private views. Located at the desirable Summerville Resort offering a PRIME location, only 10 minutes from Disney World and 20 minutes from Universal Orlando, Sea World and Aquatica. Amazing entertainment and dining within minutes from your Villa, Disney Springs, Sunset Walk, City Walk, Disney’s Boardwalk, Walmart, Starbucks and more. This Villa is hypoallergenic and carefully cleaned and sanitized. The perfect getaway for your family!

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!

An outdoor dining area features a large, custom-built farmhouse table surrounded by benches. Refreshments and fruit are displayed on the table, with a private pool visible in the background, enclosed by a screened lanai. Lush green grass complements the serene atmosphere.

4.96 out of 5 average rating, 226 reviews

★Completely Renovated★ 3 mi to Disney+Free Resort!

Closest FREE resort to Disney Parks! Sandpiper Shores is a 6 bedroom 4 bathroom luxury villa that sleeps 14. BEST STAR RATING - OVER 200 REVIEWS! * Kitchen is loaded & all baby gear provided. * Custom game room with A/C, LED panel lighting, & ROCK CLIMBING WALL! * Roku smart TVs & NEST tech throughout. * Outdoor space includes your own private pool, hot tub, overhead lighting, NEW grill, & 10' custom-built farmhouse table to seat the whole family! Every detail has been thought of!

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.

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!

5 out of 5 average rating, 115 reviews

The image features a private pool surrounded by lounge chairs, with a basketball hoop and a lush green backdrop. An entertainment area is visible in the foreground, showcasing a game table, a digital pinball machine, and a large screen for movies and games, including a fun tube slide.

Home in Four Corners

*NEW* Space Odyssey: Pool, Spa, Cinema, Games+PS5

Stylish Design, Luxurious Comfort & Endless Entertainment, with a sprawling 2200 ft2 southwest facing pool deck & outdoor kitchen, no rear neighbors on a beautiful forest in the stunning 3.5 square mile Reunion Resort. You will have your own private pool with overflow spa, movie room, billiards - game room, 4 theme rooms: OUTER SPACE, MARVEL SUPERHEROES with a TUBE SLIDE, FROZEN II, HARRY POTTER CUPBOARD, PS5, within minutes to Disney.

4.83 out of 5 average rating, 6 reviews

Themed Rooms • Private Pool • Family Dream Stay

Step into a fully themed, design-forward escape just minutes from Walt Disney World®, where every room tells a story and every detail is curated for unforgettable stays. Whether you're here for family fun or a magical getaway, this home blends comfort, style, and experience in one place. Unwind in your private pool and spa overlooking the tranquil Windsor Hills lake—where sunset swims and quiet mornings become part of the memory.

Popular amenities for Windsor Hills house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 17 reviews

The Disney House • Immersive Rooms • Gaming Lounge

A spacious two-story villa is surrounded by a manicured lawn and tropical landscaping. A paved driveway leads up to the entrance, framed by palm trees and vibrant greenery. The exterior features a light-colored stucco finish and a welcoming front porch.

4.89 out of 5 average rating, 19 reviews

5BD Formosa Gardens Near Disney (FG 7939)

4.97 out of 5 average rating, 78 reviews

Fantastic home just 3 miles from Disney World!

A welcoming entryway is highlighted by a wooden staircase with white railing and a decorative mural on the wall. A green velvet bench sits beside a woven basket. A vibrant neon sign reads 'The happiest place on earth,' adding a cheerful touch to the space.

5 out of 5 average rating, 17 reviews

Disney & ESPN Sports | Pool + Hot Tub | Game Room

A spacious poolside dining area is featured, with a large table set for meals. Elegant place settings include green plates and silverware. A large screen is visible, showcasing outdoor entertainment, with colorful sunset hues reflecting through the screened enclosure.

4.94 out of 5 average rating, 82 reviews

8 Mins To Disney W/Poolside Theater & Games Room

4.98 out of 5 average rating, 84 reviews

The exterior of a large, two-story home is displayed, featuring a light-colored facade and a covered front porch. Lush landscaping surrounds the driveway, which is paved with stone. A garage door is positioned on the right side, complemented by decorative lanterns and palm trees.

Home in Osceola County

Large Private Home on Golf course by Disney

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

4.83 out of 5 average rating, 6 reviews

Newly Updated Windsor Hills 5 bed/5 bath Pool Home

Weekly house rentals

A movie room designed for family entertainment features comfortable seating arranged in rows facing a large screen displaying animated characters. The walls are dark, enhancing the cinematic experience, while a framed movie poster adds a touch of décor to the space.

4.8 out of 5 average rating, 115 reviews

*Windsor Hills Ohana Oasis* 4/4 Disney Pool Home

4.83 out of 5 average rating, 12 reviews

10 Min to Disney • Heated Pool • Free Water Park

4.86 out of 5 average rating, 7 reviews

Our Happily Ever After House 10 Min To Disney

4.8 out of 5 average rating, 5 reviews

2 Miles To Disney, Lake View Pool Home

5 out of 5 average rating, 7 reviews

Premium 4BR Home near Disney | Windsor Hills

5 out of 5 average rating, 3 reviews

7839 6BD Beautiful Family Home in Reunion Resort

5 out of 5 average rating, 28 reviews

Private Pool~BabyReady~Princess Playroom~Waterpark

A comfortable living area features leather seating arranged around a decorative coffee table. A large television is mounted on the wall, displaying a serene outdoor scene. Sliding glass doors provide a view of the private patio and pool area, enhancing natural light within the space.

4.67 out of 5 average rating, 119 reviews

Stunning Home w Private Pool & Spa, Free Waterpark

Private house rentals

4.8 out of 5 average rating, 20 reviews

Welcome to The Windsor Dream!

A spacious two-story villa stands in a well-kept community, featuring a tile roof and decorative front door. Lush green landscaping surrounds the entrance, with neatly trimmed shrubs and grass. The driveway is clear and offers parking space for multiple vehicles.

4.77 out of 5 average rating, 35 reviews

6BR/5BA DisneyVilla, Pool+Spa, GameRoom, Clubhouse

The two-story villa features a well-maintained exterior with a spacious driveway and lush landscaping. Inside, a colorful themed bedroom is seen, showcasing custom wall art alongside twin beds with vibrant bedding. An outdoor area with a private pool and spa is enclosed by a screened patio.

4.86 out of 5 average rating, 14 reviews

Hilltop Villa: Star Wars/Princess room near Disney

A dining area features a long wooden table set for ten, accompanied by white upholstered chairs. Decorative plates and turquoise glasses are arranged neatly. Large windows allow natural light to fill the space, and modern artwork adorns the walls, enhancing the overall aesthetic.

4.89 out of 5 average rating, 28 reviews

Dazzling 5 bedroom Windsor Hills Home 7781

5 out of 5 average rating, 5 reviews

Luxury 5BR Villa 2 Miles to Disney with Game Room

4.88 out of 5 average rating, 8 reviews

6BR | Movie Theater | Themed Bedrooms | Pool & Spa

An Avengers-themed game room is presented, featuring arcade games such as a pinball machine and a dancing game. A basketball shoot machine is visible, along with colorful graphics on the wall depicting a city skyline. The floor is covered in black matting for comfort.

4.84 out of 5 average rating, 19 reviews

Windsor Hills 4BR Villa | Private Pool + Game Room

The front exterior of the property is displayed, featuring a two-car garage and a welcoming entrance. Lush greenery is visible around the property, complemented by neatly trimmed bushes and trees. The light exterior of the house is contrasted against a clear blue sky.