House vacation rentals in Windsor Hills

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Top-rated house rentals in Windsor Hills

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Top guest favorite
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.
Home in Kissimmee
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.

Superhost
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.
Home in Kissimmee
4.82 out of 5 average rating, 135 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

Top guest favorite
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.
Home in Kissimmee
4.99 out of 5 average rating, 140 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.

Guest favorite
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.
Home in Kissimmee
4.88 out of 5 average rating, 120 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!

Guest favorite
The exterior of the home features a spacious driveway, paved in light-colored bricks, leading up to an attached garage with an ornate door. A well-maintained lawn with green grass and palm trees is visible, complemented by a clear blue sky filled with clouds.
Home in Kissimmee
4.8 out of 5 average rating, 111 reviews

View the Disney fireworks from your pool!

Our home is close to Walt Disney World - Shopping - Restaurants . You’ll love the fully stocked granite kitchen, ALL SMART TVs in EVERY room, the views (fireworks), the location, the high ceilings & ceiling fans. Our home is great for couples, families (with kids), and furry friends (pets). Laundry room is INSIDE. The garage is full of games (air hockey, pool & foosball) The pool has a covered lanai with table & chairs for outdoor eating while overlooking our lake with a lighted fountain.

Top guest favorite
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.
Home in Kissimmee
4.96 out of 5 average rating, 172 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.

Guest favorite
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.
Home in Kissimmee
4.97 out of 5 average rating, 143 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

Top guest favorite
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.
Home in Kissimmee
5 out of 5 average rating, 239 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.

Top guest favorite
The exterior of a two-story home is shown, featuring a well-maintained lawn and a paved driveway leading to a two-car garage. A circular entrance is highlighted by a decorative front door, with large windows allowing natural light to flow inside. The sky is partly cloudy.
Home in Kissimmee
4.96 out of 5 average rating, 107 reviews

Manor on Knottingham Near Disney

Welcome to "Manor on Knottingham," nestled in the heart of Four Corners. The rustic charm, adorned with vintage Disney-inspired decor, transports guests to a bygone era of beloved characters and timeless tales. Outside, enjoy the sparkling blue pool and warm summer weather. A great place for family and friends. "Manor on. Knottingham" promises an extraordinary stay, where the magic of Disney and the comfort of a home merge into an unforgettable experience.

Guest favorite
A spacious living room features a large sectional sofa adorned with blue and white cushions. A glass coffee table is centered on a soft area rug. Large sliding doors provide views of the pool area, while a flat-screen TV displays a colorful image. Decorative plants add a welcoming touch.
Home in Davenport
4.85 out of 5 average rating, 122 reviews

Beautiful 3BR Home Heated Pool Game Room by Disney

Relax with the whole family at this peaceful HEATED POOL house in Davenport, just miles from Disney World Theme Parks, Universal Studios and Legoland in Orlando Florida. Master Suite has sliding doors and great view to screened Pool & Lanai. 3 bedrooms, 2 bathrooms, fully equipped kitchen, 3 Smart LED TV's and strong Wi-Fi all around the house. Enjoy our Games Room with Indoor Basketball and Pool Table located in the garage! Parking is in the driveway.

Guest favorite
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.
Home in Kissimmee
4.82 out of 5 average rating, 135 reviews

Park Place! 7 Min from Disney, Pool, Theater

Elevate your next getaway at this outstanding 5-bedroom, 3-bathroom home! Nestled in an upscale, gated community, Park Place boasts 2500 sq. ft. of beautiful living space and easily accommodates 10 guests. This home is ideal for families or a small group visiting the magical Orlando area’s countless attractions. Ideally located between theme parks, shops, and restaurants, you're perfectly situated to experience all the area has to offer!

Guest favorite
The exterior of a two-story yellow cottage is shown, featuring large windows and a fenced private pool. Sunlight reflects off the water, and lush greenery surrounds the pool area, enhancing the inviting atmosphere. Balconies are visible on the upper level, overlooking the pool.
Home in Kissimmee
4.96 out of 5 average rating, 227 reviews

"Vista Lago"Hotel Amenities/lake view,private pool

HOTEL AMENITIES , Reach out to the host if you find similar cottage for cheaper prices for possible price match ( not guaranteed) WHY THIS SPECIFIC COTTAGE IN MARGARITAVILLE ??? ( In the next description we will clarify the difference between this cottage which is rented as a 3 Bedroom Elite Cottage and other different cottages in Margaritaville so you have a clear view to choose the best cottage that fits your needs : ↓ ↓

Popular amenities for Windsor Hills house rentals

When is the best time to visit Windsor Hills?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR4,008 ZARR4,008 ZARR4,316 ZARR4,265 ZARR3,768 ZARR4,042 ZARR4,179 ZARR3,837 ZARR3,528 ZARR3,734 ZARR3,956 ZARR4,436 ZAR
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

Quick stats about house rentals in Windsor Hills

  • Total vacation rentals

    Explore 360 vacation rentals in Windsor Hills

  • Nightly prices starting at

    Windsor Hills vacation rentals start at R1,199 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 9,130 verified reviews to help you choose

  • Family-friendly vacation rentals

    350 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    350 properties feature pools

  • Rentals with dedicated workspaces

    210 properties have a dedicated workspace

  • Wi-Fi availability

    350 of Windsor Hills vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Windsor Hills rentals

  • 4.7 Average rating

    Windsor Hills stays receive an average rating of 4.7 out of 5 from guests

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