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, 107 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, 122 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!

The exterior of the house displays a light blue facade with white trim and multiple windows. A well-manicured garden with shrubs borders the entrance, while a concrete pathway leads to the front door. Tall trees provide shade in the front yard.

4.88 out of 5 average rating, 217 reviews

Disney Home Windsor Hills 3BED 3BATH Pool Parking

Recently renovated. Steps to Clubhouse + no rear neighbour. 500 mb wi-fi! The Disney Vacation Home is well located: the resort is one of the closest to the parks entrances. 10 minutes away from Animal Kingdom, Epcot, Hollywood Studios and 25 minutes away from Universal Studios, Island of Adventure and Volcano Bay. With an easy access to the airport (US 192, FL 417 and I-4 roads), Downtown Orlando, Miami and all the attractions in Central Florida (Daytona Beach, Clearwater and St. Petersburg).

A spacious living area features a comfortable dark gray sofa and a stylish coffee table, surrounded by neutral decor. A large flat-screen TV is positioned on a modern console against a bright wall, while natural light fills the space through multiple windows.

4.97 out of 5 average rating, 165 reviews

Cozy Disney Oasis Pool Home 10 Mins from Parks!

Our charming, pet-friendly home is located in the prime area of Kissimmee, Florida. Your family will be close to Disney parks, restaurants, Old Town, and Downtown Disney. Just bring your bag—we have everything you need! Settle into our fully equipped home, thoughtfully designed to create lasting memories with family and friends. Enjoy the Florida weather by cooling off in our open-air pool or grilling by the poolside lounges. Relax in our airy bedrooms, including Mickey and Minnie themed rooms!

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, 174 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.

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, 145 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

5 out of 5 average rating, 5 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 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.

4.88 out of 5 average rating, 128 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 game room is presented with a red and neutral color scheme, featuring a billiard table with a set of colorful pool balls arranged on it. A television is mounted on the wall, and a dartboard is visible. The space is accented with vibrant wall art and seating areas.

4.9 out of 5 average rating, 128 reviews

No Airbnb Fee | Newly Renovated 4BR w/ Pool!

**We offer EV Charger for FREE!!! The magic of Orlando starts at home! This incredible house has much more than you need; it has everything you WANT! We offer guests comfort, convenience and an amazing experience!! Transparency and communication is very important to us! We want to make it clear, that we are here at your disposal for any doubts or suggestions. We can't wait to have you here enjoying peace and quiet and having lots of fun!

Popular amenities for Windsor Hills house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A serene pool area is enclosed by a screened lanai, featuring a clear blue pool complemented by a built-in hot tub. Two white lounge chairs are positioned alongside the pool, surrounded by lush greenery visible through the screens.

4.83 out of 5 average rating, 81 reviews

Windsor Hills Resort Home Disney Free Pool Heat

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, 82 reviews

Disney Pool Villa | Windsor Hills | Sleeps 8

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

4.97 out of 5 average rating, 73 reviews

Home mins to Disney, pool, arcade, waterslides

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.

4.74 out of 5 average rating, 27 reviews

Windsor Hills Town Home

4.95 out of 5 average rating, 38 reviews

Hot Deals! Free Waterpark, Close to Disney

An immersive game room features themed decor, multiple gaming stations, and comfortable seating. Bunk beds create a playful atmosphere in a Star Wars-themed bedroom. A stylish living area displays modern furniture and decor, while a private pool area is surrounded by screens, showcasing outdoor seating and lush greenery.

4.88 out of 5 average rating, 32 reviews

5 BR Oasis By Disney | Game Rm + Themed BRs + 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

A vibrant water play area features colorful slides and fountains, offering a fun and engaging experience for children. The blue surface reflects sunlight, enhancing the cheerful ambiance. Palm trees and resort buildings are visible in the background, contributing to the leisure environment.

4.63 out of 5 average rating, 30 reviews

La Dolce Vita | Gated resort

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.

4.87 out of 5 average rating, 15 reviews

5BD Formosa Gardens Near Disney (FG 7939)

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, 21 reviews

Dazzling 5 bedroom Windsor Hills Home 7781

4.81 out of 5 average rating, 26 reviews

Themed Rooms with Private Pool in Kissimmee

A private screened patio features a dining set with a glass table and wicker chairs, overlooking a serene lake. The clear blue sky is reflected in the water, while a pool glistens nearby, creating a peaceful outdoor space.

4.96 out of 5 average rating, 49 reviews

Serene 6BR Retreat | Pool, Lake View, Near Disney

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, 17 reviews

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

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.

4.96 out of 5 average rating, 82 reviews

NEW Stunning Villa located 5-10 Min from Disney

Private house rentals

5 out of 5 average rating, 11 reviews

Magic Stay near Disney

A cozy living area features a large sectional sofa with decorative pillows, positioned near a wall-mounted flat-screen television. A light-colored coffee table and a woven basket are present. Natural light fills the room through the large window, adorned with white blinds, creating a welcoming ambiance.

4.91 out of 5 average rating, 93 reviews

Resort 2 bedroom Townhome near Disney World

4.99 out of 5 average rating, 85 reviews

Home in Davenport

Pool & Spa Oasis/Golf Retreat/Near Disney/3BR Home

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, 37 reviews

Luxurious home 2 miles from Disney - Windsor Hill

A private pool area is enclosed by a screen enclosure, featuring a clear blue swimming pool and a heated spa. Lush greenery surrounds the space, with views of a serene lake visible through the mesh walls, inviting relaxation under a bright sky.

4.94 out of 5 average rating, 97 reviews

Lakeside Paradise, 15 min Disney + Saltwater Pool

A screened-in outdoor area features a private pool surrounded by a patio. Lounge chairs are positioned beside the pool, offering a relaxed space for sunbathing. Lush greenery is visible beyond the enclosure, creating a tranquil setting for outdoor enjoyment.

4.92 out of 5 average rating, 61 reviews

5BR Home w/Pool near Disney Animal Kingdom

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.