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, 15 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, 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.

4.94 out of 5 average rating, 192 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!

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, 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!

Superhost

5 out of 5 average rating, 4 reviews

Disney Escape – 5-Bed Villa with Pool

Welcome to your ultimate vacation getaway at the highly desirable Windsor Hills Resort! This modern and spacious 5-bedroom, 5-bathroom villa with a private pool, spa, themed kids’ rooms, and a fully equipped game room is perfect for large families or groups seeking comfort, privacy, and convenience. Each bedroom features its own ensuite bathroom, ensuring everyone can relax in their own private retreat after a fun-filled day exploring all the attractions Orlando has to offer.

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, 148 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, 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.

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, 127 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.

5 out of 5 average rating, 67 reviews

3 Miles 2 Disney | DisneyThemed | Fully Renovated

✩Welcome to Belle's Villa in Windsor Hills✩ Calling all Disney enthusiasts! Located just 5 minutes from the enchantment of Disney and a mere 2 minutes from an array of restaurants, supermarkets, souvenir shops, and highways, this property is an ideal haven for families and kids. Immerse yourself in the magic with this beautifully renovated townhome that boasts a fully equipped kitchen, free parking, and access to the extensive amenities at Windsor Hills.

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.

4.82 out of 5 average rating, 152 reviews

Themed Pool Home 2 Miles to Disney

Welcome to your dream vacation home! - Newly remodeled 3 bedroom, 3 bathroom townhome with themed rooms - Private splash pool, fully screened-in - Prestigious Windsor Hills Resort with no resort fee - Access to a new kids water park, clubhouse, gym, and more - Free Wifi and fast internet for your Zoom meetings - 24 hour security and gated access - Have a pet? $150 pet fee on 1st; $75 each additional pet - Check out our 5 Star Reviews!

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, 17 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!

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.

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, Four Corners vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Windsor Hills, Four Corners home rentals

A cozy bedroom features two spacious beds adorned with soft blankets, complemented by a textured throw across the foot. Large windows allow natural light to fill the room, while a stunning mural of a starship cockpit sets a thematic accent on the wall.

4.94 out of 5 average rating, 35 reviews

A Galaxy?s Edge Experience Awaits! 5 Min to Disney

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.

4.91 out of 5 average rating, 32 reviews

Themed villa w Pvt Pool near Disney|Gameroom, BBQ

An expansive lagoon-style pool is surrounded by lush palm trees and comfortable seating areas, inviting relaxation. Below, a dining table is set with white plates, bowls, and cutlery, arranged on a decorative placemat, showcasing a cozy dining atmosphere.

4.96 out of 5 average rating, 81 reviews

Disney Pool Villa | Windsor Hills | Sleeps 8

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, 69 reviews

Themed Windsor Hills 6BR Private Pool Gameroom

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.

4.91 out of 5 average rating, 55 reviews

ReDesigned | Windsor Hills | Location | Water Park

A tranquil pool area features a clear blue pool and adjacent spa, both enclosed within a screened-in area. Lush greenery is visible beyond the pool deck, with a serene lake view in the background under a bright, blue sky.

4.92 out of 5 average rating, 84 reviews

Windsor Hills 5 bed/5 bath Pool Home, Games Room

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.

4.88 out of 5 average rating, 121 reviews

Disney Escape at Windsor Hills

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.

4.86 out of 5 average rating, 132 reviews

Resort Home 3.5 miles to Disney with home theater

Other great vacation rentals in Windsor Hills

5 out of 5 average rating, 3 reviews

Windsor Hills 4BR Pool Home + Mario Game Room

4.98 out of 5 average rating, 89 reviews

Luxury Disney Townhome, Mickey POOL, Water Slides,

5 out of 5 average rating, 5 reviews

Newly Renovated 6 Bedroom Windsor Hills Disney Hom

A serene pool area is featured, featuring a sparkling blue pool illuminated by soft lighting. A screened enclosure allows for a clear view of the Reedy Creek Lake conservation area, with patio space available for relaxation.

5 out of 5 average rating, 5 reviews

Upscale Fam Villa w/ Pool & Lake View, Near Disney

4.94 out of 5 average rating, 51 reviews

Themed Family Pool Home 10 Min to Disney Game Room

5 out of 5 average rating, 30 reviews

BRAND NEW 3 mi to Disney Clean Modern Diamond

5 out of 5 average rating, 30 reviews

Once upon a galaxy: Star Wars/fairytale retreat

An open-plan living area features a comfortable sofa beside a wooden coffee table, set against a backdrop of a vibrant landscape artwork. A well-equipped kitchen with modern cabinetry and bar seating is visible, illuminated by natural light flowing through large windows.