Vacation rentals in Windsor Hills

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, 13 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, 139 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 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, 118 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!

5 out of 5 average rating, 8 reviews

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

Spectacular 5 Bedroom, 5 Bathroom, Single-Family House located in the popular gated Windsor Hills Community, only 2.5 miles to Disney. This fully furnished home is perfect for your next vacation. We offer a fully-equipped kitchen with a serene breakfast nook. Unwind in our Game Room with a Pool table, Marvel theming, 80" TV, and Air Conditioning. A spacious family room overlooks a private lanai and south-facing, screened-in pool. Three bedrooms are located on the first floor with two additiona

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, 137 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 playful bedroom features a wooden loft bed designed like a house, accompanied by a sturdy ladder. Soft bedding is arranged inside the loft. A colorful light fixture hangs from the ceiling, illuminating the room. A closet door can be seen in the background, beside a vibrant wall poster.

4.95 out of 5 average rating, 41 reviews

4 bed/ 4 bath Windsor Hills

Closest homes with pools to Disney 10-15 minutes drive. Walmart groceries, Starbucks 5 minutes very near. amenities liquor, pharmacies, smoke shops, restaurants, gas. Highway 192 close by.. 5 - 10 minutes in car. the full cancellation is meant for hurricanes, pandemics, etc. other exigencies. please don't book the house and tie up the calendar for many months only to cancel 10 days prior - it makes it harder to book last minute and cover mortgage and expenses on our side, etc.

A cozy media room is designed with a Harry Potter theme, featuring a large flat-screen TV mounted on a wall. Comfortable sofas with colorful cushions are arranged around a carpet, while gaming stations are visible in the background. Framed artwork and decorative elements enhance the themed atmosphere.

5 out of 5 average rating, 70 reviews

Mickey's Pool House

Mickey's Pool House Retreat is a luxury villa with 4 bedrooms and 4 bathrooms located in the highly desirable Windsor Hills Resort and just 2 miles from the gates of Disney World. Our well equipped villa has a private screened in heated pool and spa and Harry Potter themed game/theater room. Windsor Hills is a beautiful resort that has a clubhouse and large heated resort pool with two large slides and kids splash pad. We have everything that you need to enjoy a relaxing vacation.

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, 147 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.

5 out of 5 average rating, 237 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 two-story vacation home is showcased with a tiled roof and a well-maintained front yard. Flanking the house are two neighboring properties, while a paved driveway leads to a garage. Green grass surrounds the structure, and the sky features a mix of clouds and blue.

4.88 out of 5 average rating, 125 reviews

2584 - 6 Bedroom w/ Pool and Water Park Included

Welcome to Your Ultimate Vacation Escape at Windsor Hills Resort! This charming vacation home in Windsor Hills Resort offers six spacious bedrooms and is perfect for the entire family. Located in one of the finest gated communities in the area, Windsor Hills Resort features 24-hour security, ensuring only permitted guests have access to the neighborhood. We’re just a short distance from Disney parks, shopping, dining, and many of Orlando’s top attractions.

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.

5 out of 5 average rating, 15 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!

4.91 out of 5 average rating, 242 reviews

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

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, Four Corners vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Windsor Hills, Four Corners home rentals

A tranquil outdoor space features a private pool under a protective screen enclosure, framed by reclining lounge chairs. The setting offers a view of the lake, contrasting with the colorful sunset sky, creating a serene atmosphere for relaxation.

4.98 out of 5 average rating, 106 reviews

Mickey's Lakefront Villa at Sunset Lakes

A private swimming pool is surrounded by a screened enclosure, featuring a poolside theatre with a large projector screen. Lush greenery is visible beyond the pool area, creating a serene environment. Lounge chairs are positioned nearby for relaxation.

4.9 out of 5 average rating, 112 reviews

8 mins. to Disney W/Poolside Theater & Game Room

4.79 out of 5 average rating, 19 reviews

Themed Rooms with Private Pool in Kissimmee

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, 51 reviews

ReDesigned | Windsor Hills | Location | Water Park

5 out of 5 average rating, 18 reviews

Fun+Game Room+Outdoor Theater+Themed BRs+Pool/Spa

A vibrant game room features a Star Wars theme, including life-size characters and a pool table. A cozy lounge area showcases a television. An outdoor space reveals a poolside bar with colorful stools and a movie screen beside the inviting private pool.

5 out of 5 average rating, 8 reviews

EPIC! Themed-Arcade-Theatre-Pool Table-3mi>Disney

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.

4.85 out of 5 average rating, 130 reviews

Resort Home 3.5 miles to Disney with home theater

A spacious living area features a large sectional sofa, paired with a round coffee table. Natural light floods in through sliding glass doors that open to the pool area. Decorative accents include coastal-themed artwork and soft lighting fixtures, enhancing the inviting ambiance.

4.82 out of 5 average rating, 135 reviews

Park Place! 7 Min from Disney, Pool, Theater

Windsor Hills, Four Corners condo rentals

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.

4.95 out of 5 average rating, 159 reviews

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

The living room features a comfortable sofa with colorful accent pillows, a coffee table, and a flat-screen TV mounted on the wall. A round dining table with chairs is visible in the background, along with artwork and decor that add a touch of elegance.

4.86 out of 5 average rating, 213 reviews

@Look@ ~ 3bed/2bath/1st floor! ~ Sleeps 7!

A bright living area features a comfortable brown sofa and loveseat, accented with decorative pillows. A modern coffee table is centered on tiles that enhance the spaciousness. Natural light filters through large windows, while a flat-screen TV is mounted on the wall, framed by stylish light curtains.

4.85 out of 5 average rating, 157 reviews

Star Wars Condo in Windsor Hills 3 bdrm, 2 baths

A vibrant outdoor water park is depicted, featuring two large water slides and a colorful kids' splash area. Surrounding palm trees provide shade, and a spacious pool area is visible in the background, inviting relaxation and fun.

4.9 out of 5 average rating, 213 reviews

Disney's Doorstep, 3 Bed 2 Bath, Waterslides!

4.83 out of 5 average rating, 300 reviews

Beautiful 2/2 Gem, 2 mi to Disney with Water Park!

A Star Wars themed bedroom features two twin beds with themed bedding. A decorative quilt with a pattern of star fighters is placed over one bed, while the other is dressed in a space-themed cover. A bedside table holds a lamp shaped like a lightsaber, with blue walls adorned with framed artwork.

4.92 out of 5 average rating, 176 reviews

Themed Resort Condo | Pool | Spa | Mins to Disney

A spacious pool area is surrounded by palm trees and tropical landscaping. Sun loungers line the pool deck, and a water park with slides is visible nearby. The multi-level condo buildings create a vibrant backdrop, ensuring a family-friendly environment.

4.79 out of 5 average rating, 144 reviews

Lovely vacation condo close to Disney & Universal!

A spacious pool area is featured, surrounded by palm trees and lounge chairs. The expansive waterpark includes vibrant waterslides, providing a lively atmosphere. A relaxing hot tub is also visible nearby, complemented by a well-maintained landscaping that enhances the resort's inviting ambiance.

4.98 out of 5 average rating, 176 reviews

Poolside 3Br~Windsor Hills~Waterpark~2mi to Disney

Other great vacation rentals in Windsor Hills

4.94 out of 5 average rating, 32 reviews

Awesome 4 Suites Villa 5 Min to Disney

Superhost

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.

4.9 out of 5 average rating, 20 reviews

Dazzling 5 bedroom Windsor Hills Home 7781

A two-story villa is presented with a tiled roof and a welcoming front entrance. Lush greenery and flowering plants enhance the manicured lawn, while a spacious driveway leads to a two-car garage. Clear skies provide a bright backdrop to the home's inviting façade.

4.91 out of 5 average rating, 23 reviews

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

5 out of 5 average rating, 12 reviews

4 minutes to Disney - Sleeps 14, Arcade, Pool

A private heated pool area is surrounded by a screened enclosure, featuring lounge chairs and outdoor dining options. The pool is complemented by multi-colored lights, creating an inviting space. The image also includes three themed kids' bedrooms, showcasing vibrant decor and comfortable sleeping arrangements.

4.9 out of 5 average rating, 67 reviews

Themed Windsor Hills 6BR Private Pool Gameroom

A spacious resort pool area is surrounded by palm trees, featuring a large pool with lounge chairs and umbrellas. A water slide and children's play area are visible in the background, while a building with a sloped roof provides amenities and shade to guests.

4.87 out of 5 average rating, 55 reviews

*Pet Friendly* Free Pool Heat - Windsor Hills

A bright living area features a comfortable brown leather sofa and stylish armchairs, with a ceiling fan overhead. Windows provide natural light, framing the view of the outdoors. A mounted flat-screen TV and decorative elements contribute to the inviting space.

5 out of 5 average rating, 33 reviews

Harry Potter Family Fun | 3BR Windsor Hills Resort