
House holiday rentals in Windsor Hills
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Top-rated house rentals in Windsor Hills
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Disney Pool Villa | Windsor Hills | Sleeps 8
BOOK EARLY! Rated top 1% & Guest Favorite. Our popular home fills up 3-4 months in advance. 3BR/3BA Private Pool Villa in Windsor Hills Resort, Kissimmee! Newly renovated, gated resort, 3 miles to Disney World. Modern beach-coastal design, updated kitchen, family-friendly layout. Free parking, Wi-Fi, full resort access (pool, splash park, gym, playground). Near Universal (20 min), SeaWorld (18 min), Legoland (40 min). Perfect location for vacations Disney trips, sports events, and conventions.

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

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

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.

Cinderella's HolidayVilla-Minutes from Disney-NEW!
• 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 FULLY REMODELED in Sept 2022!

NEW Stunning Villa located 5-10 Min from Disney
Welcome to this BRAND-NEW dreamscape Vacation Villa with private views. Located at the desirable Summerville Resort offering a PRIME location, only 10 minutes from Disney World and 20 minutes from Universal Orlando, Sea World and Aquatica. Amazing entertainment and dining within minutes from your Villa, Disney Springs, Sunset Walk, City Walk, Disney’s Boardwalk, Walmart, Starbucks and more. This Villa is hypoallergenic and carefully cleaned and sanitized. The perfect getaway for your family!

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!

★Completely Renovated★ 3 mi to Disney+Free Resort!
Closest FREE resort to Disney Parks! Sandpiper Shores is a 6 bedroom 4 bathroom luxury villa that sleeps 14. BEST STAR RATING - OVER 200 REVIEWS! * Kitchen is loaded & all baby gear provided. * Custom game room with A/C, LED panel lighting, & ROCK CLIMBING WALL! * Roku smart TVs & NEST tech throughout. * Outdoor space includes your own private pool, hot tub, overhead lighting, NEW grill, & 10' custom-built farmhouse table to seat the whole family! Every detail has been thought of!

Luxury 2 Master Suite Pool Hot Tub Pool Table BBQ
Welcome to Mickey's Landing. A beautifully renovated home featuring four bedrooms, three bathrooms, two luxurious master suites, a fully equipped chef’s kitchen, a game room, and a private screened-in pool with an above-ground hot tub. It is just two miles from Disney World and combines whimsical Disney charm with modern comforts like high-speed WiFi and Smart TVs. Perfect for families or groups, it’s the ultimate destination for relaxation, adventure, and creating unforgettable memories.

Dream Stay: Resort Pool Villa minutes to Disney
Welcome to this recently renovated 6B/4B pool/hot tub villa in the coveted Windsor Hills Resort: ○ 3 miles from Disney Parks ○ X-Men themed game room with Wii console and arcades ○ Private pool and spa ○ Short walk to clubhouse with pool & slides ○ High speed Wi-Fi ○ Themed kid's rooms including Disney princess and dragons ○ Top rated gated resort community *Windsor Hills* with amenities including water park, waterslide, arcade room, movie room, gym, playground, tennis courts & more

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.

Hibiscus Villa w/ themed rooms, game room and pool
Welcome to your luxurious single story 4-bedroom getaway in the heart of a gated resort just 2.6 miles from the magic of Disney World! This meticulously designed vacation home offers not only comfort and convenience but also an array of resort amenities that promise an unforgettable stay. Your dream vacation home is not just a place to stay; it's a gateway to a world of enchantment and relaxation. Book your stay now and let the magic begin!
Popular amenities for Windsor Hills house rentals
House rentals with a pool

5BD Formosa Gardens Near Disney (FG 7939)

Charlie's Funhouse and Games near Animal Kingdom

15 minutes to Disney - Sleeps 14, Arcade, Pool

Once upon a galaxy: Star Wars/fairytale retreat

Disney & ESPN Sports | Pool + Hot Tub | Game Room

Fantastic home just 3 miles from Disney World!

8 Mins To Disney W/Poolside Theater & Games Room

Family Disney Home | Pool | Game Room | Hot Tub
Weekly house rentals

The Disney House • Immersive Rooms • Gaming Lounge

*Windsor Hills Ohana Oasis* 4/4 Disney Pool Home

10 Min to Disney • Heated Pool • Free Water Park

Gorgeous 5BR at Encore Resort next to Disney - 305

Callaghan Cantina

Windsor Hills Home w/Arcade Game Room|Near Disney

ReDesigned | Windsor Hills | Location | Water Park

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

Welcome to The Windsor Dream!

6BR/5BA DisneyVilla, Pool+Spa, GameRoom, Clubhouse

Hilltop Villa: Star Wars/Princess room near Disney

Luxury 5BR Villa 2 Miles to Disney with Game Room

Spacious Kissimmee Villa - 3 Mi to Disney World!

2 Miles To Disney, Lake View Pool Home

Premium 4BR Home near Disney | Windsor Hills

Windsor Hills 5 bedroom home with private pool
When is the best time to visit Windsor Hills?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $327 AUD | $327 AUD | $352 AUD | $348 AUD | $308 AUD | $330 AUD | $341 AUD | $313 AUD | $288 AUD | $315 AUD | $348 AUD | $400 AUD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Quick stats about house rentals in Windsor Hills

Total holiday rentals
Explore 360 holiday rentals in Windsor Hills

Nightly prices starting at
Windsor Hills holiday rentals start at $112 AUD per night before taxes and fees

Verified guest reviews
Over 9,480 verified reviews to help you choose

Family-friendly holiday rentals
350 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Holiday rentals with a pool
350 properties feature pools

Rentals with dedicated workspaces
210 properties have a dedicated workspace

Wi-Fi availability
360 of Windsor Hills holiday 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
Destinations to explore
- Rentals with a washing machine and dryer Windsor Hills
- Villa rentals Windsor Hills
- Fitness-friendly rentals Windsor Hills
- Serviced apartment rentals Windsor Hills
- Pet-friendly rentals Windsor Hills
- Condo rentals Windsor Hills
- Rentals with a home theatre Windsor Hills
- Rentals with a hot tub Windsor Hills
- Rentals with pools Windsor Hills
- Rentals with an EV charger Windsor Hills
- Family-friendly rentals Windsor Hills
- Apartment rentals Windsor Hills
- Rentals with a patio Windsor Hills
- Rentals with outdoor seating Windsor Hills
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- Walt Disney World Resort
- Universal Studios Florida
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Orange County Convention Center
- Disney Springs
- Magic Kingdom Park
- SeaWorld Orlando
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Discovery Cove
- Epcot
- ESPN Wide World of Sports
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Southern Dunes Golf and Country Club
- University of Central Florida




