House holiday rentals in Windsor Hills

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

Updated Pics Dec 2024. We have no gas burning appliances. We abide by the AirBnB enhanced cleaning protocol. We want our guests to be happy, healthy and safe in their home away from home. Please see house rules. Located in beautiful Sunset Lakes – it's hard to find a vacation home closer to Walt Disney World with all that's offered at Mickey’s Lakefront Villa. Be amazed at how quiet and secluded you will feel yet just minutes away from all of the entertainment that you came here to enjoy.

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.

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

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!

A serene backyard pool area is enclosed by a screened lanai, featuring two lounge chairs adorned with vibrant blue and green cushions. Lush greenery and trees are visible beyond the pool, enhancing the peaceful view. The clear water reflects the cloud-dotted sky.

4.96 out of 5 average rating, 173 reviews

4 bedroom, south facing pool 3 miles to Disney

Create family memories in our stunning pool home with Star Wars, Minnie and Mickie themed twin rooms. Elegant and comfortable king bed master bedroom with your own private bathroom and soaking tub! Delightful queen bedroom that also features its own private bathroom with shower. Enjoy a heated south facing pool (heating extra charge) with no rear neighbors. We are located in a guard gated community that features a large pool, clubhouse with a gym, arcade, movie room, and various sports courts.

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

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!

The exterior of the house is showcased, featuring a two-story design with light-colored walls and a prominent entrance. A spacious driveway accommodates up to four vehicles, bordered by well-maintained green lawns and trees. The property is set within a landscaped community.

4.97 out of 5 average rating, 144 reviews

Highest Rated Minutes to Disney! -Newly Renovated

• Newest house in the #1 community in the Disney Area, Windsor Hills • Only home with 7 bedrooms in the community (3 KING beds) • Extra privacy: only one side & no rear neighbors • 4 children themed bedrooms (Mickey, Star Wars, Toy Story, & Frozen) • Onsite, driveway parking for 4 vehicles • FREE pool heat + BBQ with all rentals • Fully equipped + stocked kitchen • Self check-in with digital lock • Super FAST Wi-Fi wireless internet speed at +1000 Mbps • Property is managed directly by owner

Superhost

5 out of 5 average rating, 3 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.

5 out of 5 average rating, 12 reviews

Free Waterpark|Game Room|Near Dis!

Welcome to Playcation Paradise by Cosmic Vacations. This is your dream getaway in Windsor Hills Resort—just 3 miles from Disney World, 15 miles from Universal, and only 0.4 miles to Windsor Hills’ incredible amenities! Enjoy your private pool and spa, or have a blast in the custom game room with commercial-grade arcade games set to free play. Plus, you’ll have free access to Windsor Hills’ top-tier amenities, including a lagoon-style pool, water slides, and sports courts.

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, 240 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.

4.98 out of 5 average rating, 176 reviews

*Private Modern Oasis: Pool, Spa, Cinema, Arcades

Experience the perfect blend of STYLISH DESIGN, LUXURIOUS COMFORT & ENDLESS ENTERTAINMENT in this stunning home at Reunion Resort. Enjoy a sprawling 2400 ft² southwest-facing pool deck with outdoor kitchen, private pool & overflow spa, plus no rear neighbors. Inside, find a movie room, billiards game room, STAR WARS & FROZEN II kids’ theme rooms with tube slide, and both Xbox & PlayStation for nonstop fun.

Popular amenities for house rentals in Windsor Hills

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A collage showcases a vibrant water park with colorful slides, a game room featuring a pool table and retro arcade games, a spacious villa exterior with palm landscaping, and a sunlit pool area enclosed by a screened lanai, inviting relaxation.

4.78 out of 5 average rating, 36 reviews

Luxurious home 2 miles from Disney - Windsor Hill

5 out of 5 average rating, 5 reviews

NEW!-Fun-Relaxing-Private-Beautiful Vacation Home

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

A modern kitchen area features a large island with three sleek bar stools. Stainless steel appliances, including a gas stove and microwave, complement the white cabinetry. A dining table is visible in the background, surrounded by comfortable chairs and illuminated by natural light.

4.97 out of 5 average rating, 37 reviews

Fantastic 4 Suites Villa 5 min to Disney

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 spacious entryway features a stylish staircase with wooden steps and a glass railing. A large Christmas tree decorated in soft colors stands next to a modern living area displaying a cozy sofa and contemporary artwork. A fireplace adds warmth to the ambiance.

4.83 out of 5 average rating, 46 reviews

The Eights House by Disney. Themed Island Dream

A private screened-in pool area features a softly illuminated heated pool and spa. Lounge chairs are positioned around the poolside, with a covered seating area visible in the background. The evening sky casts a serene glow over the tranquil setting.

4.89 out of 5 average rating, 28 reviews

Sunny Winter Escape Near Disney | Private Pool

An outdoor dining area is displayed, featuring a white table surrounded by six grey chairs. A large TV is mounted on the wall, showcasing a performance. A stainless steel grill is positioned nearby, complemented by drinks and a platter of fresh strawberries on the table.

5 out of 5 average rating, 39 reviews

Poolside TV, 3 Kings, FREE Waterpark, AC Game Rm

Weekly house rentals

A single-story home with a light blue exterior is framed by well-maintained greenery and a palm tree. The front porch is marked by arched windows and a double garage door. A clear path leads to the entrance, offering an inviting first impression.

5 out of 5 average rating, 20 reviews

ClosetoDisney/southpool/4bdrm

4.96 out of 5 average rating, 24 reviews

Charlie's Funhouse and Games near Animal Kingdom

5 out of 5 average rating, 30 reviews

BRAND NEW 3 mi to Disney Clean Modern Diamond

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

An inviting private pool area is shown within a screened enclosure, featuring clear blue water and a rounded pool shape. Comfortable outdoor seating is placed beside the pool, with lush greenery decoratively lining the wall, enhancing the tranquil space.

4.94 out of 5 average rating, 16 reviews

Home, Private Pool, 10 min to Disney, 3 BR/2 Baths

4.97 out of 5 average rating, 73 reviews

Home mins to Disney, pool, arcade, waterslides

5 out of 5 average rating, 19 reviews

Luxury Home | Pool, Spa | Game Room | Golf View

4.95 out of 5 average rating, 38 reviews

Hot Deals! Free Waterpark, Close to Disney

Private house rentals

5 out of 5 average rating, 3 reviews

Windsor Hills 4BR Pool Home + Mario Game Room

A cozy living area features a large grey sofa, a wall-mounted television, and natural light from expansive windows. The dining area is adorned with inviting decor. The themed bedrooms showcase playful colors and artwork, offering a welcoming environment for families, creating a vibrant atmosphere.

5 out of 5 average rating, 48 reviews

BRAND NEW. Beautiful 3BD/3BA 5 minutes from Disney

A single-story residence is framed by lush green grass and tropical landscaping. Palm trees and ornamental plants are positioned near the entrance, while a wide driveway leads to a two-car garage. Large windows allow natural light to illuminate the inviting façade.

5 out of 5 average rating, 23 reviews

Modern home with Private Pool near Disney

4.93 out of 5 average rating, 14 reviews

Disney Resort Home, Waterpark, pool/spa, FREE Heat

A spacious living room features comfortable seating arranged for relaxation and entertainment, while a large window allows natural light to brighten the area. The dining space is visible, seamlessly connected to the open kitchen design. The heated pool area showcases inviting blue water with a surrounding patio.

4.87 out of 5 average rating, 162 reviews

Contemporary Lakefront Villa, Minutes from Disney

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.

4.97 out of 5 average rating, 170 reviews

Luxury 2 Master Suite Pool Hot Tub Pool Table BBQ

Superhost

The exterior of a light blue house features a welcoming entrance with a dark blue door and decorative molding. Large windows allow natural light to illuminate the interior, surrounded by well-maintained green shrubs. The pathway leads up to the entrance, enhancing accessibility.

4.8 out of 5 average rating, 25 reviews

Windsor Hills Town Home

A well-equipped game room features a foosball table, air hockey table, and a basketball arcade game. Designed with dark-toned furniture, the space includes comfortable gaming chairs and sci-fi-themed wall artwork, creating an engaging environment for entertainment.