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Vacation rentals in Windsor Hills

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Top-rated vacation rentals in Windsor Hills

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
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.
Home in Kissimmee
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

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
4.87 out of 5 average rating, 119 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
Villa in Kissimmee
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

Top guest favorite
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.
Condo in Kissimmee
4.98 out of 5 average rating, 176 reviews

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

Your Windsor Hills Getaway starts here! This top-rated condo overlooks the resort pool & waterpark and is just minutes from Disney World! New appliances and updated furnishings, this 3rd floor condo sleeps 8, with plenty of parking. The screened-in balcony can’t be beat, overlooking the pool, hot tub, and waterpark with waterslides! The clubhouse is just steps away, with a store, food, drinks, game room, and fitness center. No resort, parking, or hidden fees. Full access to all amenities!

Top guest favorite
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.
Villa in Kissimmee
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!

Top guest favorite
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.
Villa in Kissimmee
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

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, 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.

Guest favorite
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.
Home in Kissimmee
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.

Guest favorite
The aerial view showcases a spacious pool area surrounded by lush palm trees and lounge chairs. A bright water slide is visible in the background, leading to the pool. A serene lake serves as a picturesque backdrop, enhancing the resort's atmosphere.
Condo in Kissimmee
4.86 out of 5 average rating, 193 reviews

One in a Minion condo your kids will love +450Mbps

Enjoy of sophisticated and modern accommodations on your next visit to Orlando. This One in a Minion themed two bedroom condo boasts 1082 SQ FT of living space and it's fully equipped for 6 guests. Conveniently located on the ground floor and a short stroll to the clubhouse, pool and dueling water slides. It features a smart lock, High-speed WIFI Internet +450Mbps, cable TV, telephone line, linens & towels and washer/dryer.

Superhost
A vibrant water park area is visible, featuring various slides and water attractions surrounded by lush greenery. Brightly colored murals decorate nearby walls, showcasing popular animated characters. Comfortable seating is positioned throughout, inviting relaxation while enjoying the resort's amenities.
Condo in Kissimmee
4.8 out of 5 average rating, 142 reviews

Avenger's Retreat Near Disney

Step into the magic of Disney and make unforgettable memories at your very own Avengers Retreat - Luxurious 2-bed, 2-bath condo with themed rooms - Located 2.5 miles from Disney and steps to clubhouse - Free parking and no resort fees - Family-friendly with high chair, stroller, and Pack-N-Play - Access to outdoor pool, water park, fitness center, and more - Free Wifi with 400 Mbps speed

Guest favorite
A modern keypad lock is installed on a door, featuring illuminated numbers for easy access. Blurred in the background, a vibrant green plant adds a touch of nature to the entryway, enhancing the welcoming ambiance of the space.
Guest suite in Kissimmee
4.93 out of 5 average rating, 173 reviews

It's too much like a elegant mini-hotel (7)

It's too much like a elegant mini hotel with rich artistic atmosphere! All the pictures on this page are a reflection of the real condition of the house. All the furniture has been carefully selected, and comfortable mattress and pillows will quickly accompany you into sweet dreams. The biggest feature of this house are comfort, economy and convenience.

Popular amenities for Windsor Hills, Four Corners vacation rentals

When is the best time to visit Windsor Hills?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR3,944 ZARR4,030 ZARR4,326 ZARR4,343 ZARR3,892 ZARR4,013 ZARR4,256 ZARR3,892 ZARR3,527 ZARR3,926 ZARR4,083 ZARR4,361 ZAR
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

Quick stats about vacation rentals in Windsor Hills

  • Total vacation rentals

    Explore 680 vacation rentals in Windsor Hills

  • Nightly prices starting at

    Windsor Hills vacation rentals start at R869 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 13,040 verified reviews to help you choose

  • Family-friendly vacation rentals

    620 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    670 properties feature pools

  • Rentals with dedicated workspaces

    400 properties have a dedicated workspace

  • Wi-Fi availability

    650 of Windsor Hills vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Windsor Hills rentals

  • 4.7 Average rating

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

  1. Airbnb
  2. United States
  3. Florida
  4. Osceola County
  5. Four Corners
  6. Windsor Hills