
House holiday rentals in Windsor Hills
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Top-rated house rentals in Windsor Hills
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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.

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!

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

★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!

Themed Villa:10 min to Disney: Pool, Gameroom, BBQ
Welcome to Colorful Haven, a vibrant family getaway near Disney and other top attractions. Enjoy an exceptional experience as you splash in a private pool, play fun games, enjoy outdoor dining, and relax in rooms with an amazing theme. Plus, enjoy access to resort amenities including the waterpark, sports courts, fitness center, and clubhouse. Disney World - 8 min drive Old Town - 14 min drive Universal Studios - 30 min drive Book For Unforgettable Memories In Kissimmee—See Details Below!

Disney Vacation Home w/ Pool, Hot Tub + GameRoom
Lilo’s Paradise is a great place for large families who want to enjoy the ultimate convenience and relaxation. With a private pool, comfy themed bedrooms, a fun game room, a full kitchen, and many amenities that come with the gated community, there’s something for the whole family! Plus, you’ll be just a short drive from famous attractions. Disney World - 9 min drive Old Town - 14 min drive Fun Spot America - 15 min drive Create Lasting Memories In Kissimmee With Us & Learn More Below!

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.

Spring Discounts - 6 Mi. to Disney - Plunge Pool
📍 Amazing Location Near Disney • 6 miles to Walt Disney World • 15 miles to Universal Orlando Resort • 13 miles to SeaWorld Orlando • 30 miles to LEGOLAND Florida • 25 miles to Orlando International Airport • 1 mile to Walmart, Target, Publix & dining 🏡 4 bedrooms, each with a private bath. Smart TVs in every room. Private free heated plunge pool, plus resort pool access and free parking. One of the closest communities to Disney!

Windsor Hills Single Level 4BR Home, Pool, GameRm
Welcome to this beautiful 4-bed, 4-bath Windsor Hills villa, just a few miles from Disney World! Perfect for families, this modern, spacious vacation home offers comfort, style, and access to resort amenities with no parking or resort fees. Relax, recharge, and create unforgettable memories in this family-friendly Orlando vacation rental, combining convenience, charm, and fun for an unforgettable Disney getaway.

Disney-Inspired Suites • Game Room • Summerville
Welcome to our charming 3-bedroom, 3-bathroom house, thoughtfully created to create magical moments for your entire family! Immerse yourself in our themed rooms, each capturing the magic of beloved stories like Happy Potter and Mickey Mouse. Accommodating up to 10 guests, your Disney adventure starts here! The following extra services include additional costs: Grill Early Check-in Late Check-out

8052 Heated Pool Grill House Kissimmee by Disney
Relax with the whole family at this peaceful HEATED POOL & GRILL house in Kissimmee, just minutes from Disney Parks and Margarita Ville Water Park. Master Suite has a great view to screened Pool & Lanai. 3 bedrooms, 2 bathrooms, fully equipped kitchen, 4 Smart TV's and strong Wi-Fi all around the house. Enjoy our Games Room with a Foosball table and a Pool table located in the garage!

8 mins. to Disney W/Poolside Theater & Game Room
Are you looking for a vacation home with an incredible game room, a very private south facing saltwater complimentary heated pool with children's wading pool, hot tub and poolside theatre featuring a 120" screen with 4K UHD, and a new modern kitchen, in Formosa Gardens Estates (the gated community known for its large estate lots), and is very close to Disney World? This is it . . .
Popular amenities for house rentals in Windsor Hills
House rentals with a pool

Heated pool~Lazy River~Mini Golf~Near DisneyResort

Charming vacation villa on resort w/private pool

Lakeside Magic 5BR Disney Villa w/ Pool & Lakeview

Ultimate Adventure Villa Top Rated 5 Star Disney m

NEW Stuning 09 Bedroom/LED At Pool/ Solara Resort

Elegant Disney Themes | Pool, Hot Tub & Game Room

8 Mins To Disney W/Poolside Theater & Games Room

FREE Heated Pool! 5BR Disney Villa, Themes+Games
Weekly house rentals

A Spacious and Serene Pool Home 10-min to Disney

Windsor Hills Resort 5 Bedroom Private Pool Home

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

Hilltop Villa: Star Wars/Princess room near Disney

5Bd/4Ba Game Rm Pool Spa Theater Close 2 Theme Pk

Getaway w/ Private Pool & SPA + BBQ | 10min Disney

1st Floor-Poolside -Arcade- 1.5 Miles to Disney

10 BD/ 10.5 BA Sleeps 20! Encore At Reunion(205SS)
Private house rentals

LUXE Home w Themed Rooms, Loaded Games, Disney

Welcome to The Windsor Dream!

Fun & Luxury: Home & Water Park Included

2 mi. from Disney-Mickey Mouse Villa-Windsor Hills

Magnolia View - 5 Bed 5 Bath - Gated Resort

Dream South Facing 7787

NEW LIST - Private Pool/Spa; Golf Course!

South Facing Themed Theater Swingset SplashPad BBQ
When is the best time to visit Windsor Hills?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £175 | £175 | £189 | £186 | £165 | £177 | £183 | £168 | £154 | £169 | £186 | £214 |
| 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 £67 per night before taxes and fees

Verified guest reviews
Over 9,540 verified reviews to help you choose

Family-friendly holiday rentals
350 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
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

Wifi availability
350 of Windsor Hills holiday rentals include wifi 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 hot tub Windsor Hills
- Rentals with a patio Windsor Hills
- Rentals with a washing machine and dryer Windsor Hills
- Villa rentals Windsor Hills
- Fitness-friendly rentals Windsor Hills
- Flat rentals Windsor Hills
- Rentals with pools Windsor Hills
- Family-friendly rentals Windsor Hills
- Apartment rentals Windsor Hills
- Rentals with an EV charger Windsor Hills
- Pet-friendly rentals Windsor Hills
- Rentals with outdoor seating Windsor Hills
- Rentals with a cinema Windsor Hills
- Serviced apartment rentals Windsor Hills
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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort
- Walt Disney World Resort Golf
- Disney Springs
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Give Kids the World Village
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Aquatica
- Camping World Stadium
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- Reunion Resort Golf Courses - Palmer & Watson




