Holiday rentals with a home theatre in Windsor Hills, Four Corners

4.87 out of 5 average rating, 109 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!

4.94 out of 5 average rating, 179 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!

4.97 out of 5 average rating, 123 reviews

Villa in Kissimmee

*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!

4.98 out of 5 average rating, 131 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

Condo in Kissimmee

4.85 out of 5 average rating, 152 reviews

Star Wars Condo in Windsor Hills 3 bdrm, 2 baths

Welcome to our Star Wars themed rental in Kissimmee, FL, just 3 miles from Disney World! Experience the ultimate vacation in a galaxy far, far away. Located in Windsor Hills Resort with a heated community pool and two water slides. The kids bedroom has Star Wars decor, twin bunk beds, and an electronic pinball machine. The condo is decorated with Star Wars artwork and a half-sized Darth Vader figure. The kitchen is fully equipped. Don't miss this chance to live out your Star Wars fantasies.

5 out of 5 average rating, 13 reviews

Free Waterpark, Minutes to Disney, Newly Renovated

Enjoy your stay at this gorgeous, freshly renovated home! MINUTES to Walt Disney World. 🎢 WATER SLIDES 🛝 Resort Amenities 🍽️ Entertainer's Kitchen 🏖️ Private patio with HEATED POOL ☕️ **Coffee Bar** 🧇 **Waffle Bar** 📶 Fiber High Speed Wi-Fi Thoughtfully designed for your ultimate comfort and ENJOYMENT. Beautifully updated modern interior, ceramic tile floors with Disney theming throughout. This impeccable 3 bedroom, 3 bath home comfortably sleeps up to 8 plus 2 infants/toddlers.

4.95 out of 5 average rating, 168 reviews

🏰 Disney Princess Crownhouse! Closest to Disney!

*100% 5-star reviews in 2025* *End unit* South facing pool Magical 3 bed, 3 bath luxury crownhouse in 5 star gated Windsor Hills Resort. *2 miles from the gate of Walt Disney World! Enjoy our magical Mickey and Princess Rooms designed with both adults and kids in mind. Your little princess will love our Princess room with Disney collection princess furniture. *Resort pool, a fully equipped kitchen, you and your family will have a truly magical vacation! Princess-tastic!

4.8 out of 5 average rating, 123 reviews

Themed Pool Home 2 Miles to Disney

Welcome to your perfect getaway! - Newly remodeled 3 bedroom, 3 bathroom themed private pool home - Amazing theme rooms kids will LOVE - Private splash pool fully screened-in - Free Wifi and fast internet for your Zoom meetings - Access to Windsor Hills Resort amenities, including a NEW WATER PARK - 24-hour security in a gated community - Just 2 miles from Disney and close to shopping and dining - Don't let the fun end at the parks - Every bedroom is themed!

4.97 out of 5 average rating, 151 reviews

Condo in Kissimmee

⭐️New listing 2 mi from Disney/ free water park🌊

Make your next retreat to Florida to remember when you stay at this 3-bed, 2-bath vacation rental "Mickey Star." Experience the magic of Orlando and create memories for a lifetime at your own " Magical Retreat." Conveniently situated less than 2 miles to the Disney resort, 0.5 miles to Major Supermarket, 20 min drive to Universal Studios, you can bring home the fantasy and adventure to this family-friendly condo in the highly-sought resort of Windsor Hills.

Superhost

4.82 out of 5 average rating, 130 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.

4.92 out of 5 average rating, 139 reviews

NEW Disney Dream Stay Private Pool & Waterpark

Mickey's Main Street Mania is a luxury 3 bed, 3 bath townhouse in the beautiful Windsor Hills Resort. The kids room has a beautiful Mickey Themed Mural from top to bottom. We are only 3 miles away from Disney parks and have a 24 hour gated community. Windsor Hills water park and pool is enough reason to stay but we have a beautiful themed 3 Bed/3 bathroom. The kids room is beautifully themed with custom drapes, walls, carpet, and Mickey Ceiling light.