
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.

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!

Cozy Disney Oasis Pool Home 10 Mins from Parks!
Our charming, pet-friendly home is located in the prime area of Kissimmee, Florida. Your family will be close to Disney parks, restaurants, Old Town, and Downtown Disney. Just bring your bag—we have everything you need! Settle into our fully equipped home, thoughtfully designed to create lasting memories with family and friends. Enjoy the Florida weather by cooling off in our open-air pool or grilling by the poolside lounges. Relax in our airy bedrooms, including Mickey and Minnie themed rooms!

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!

Resort 2 bedroom Townhome near Disney World
Welcome to our 2 Bed 2 bath condo with 1 car garage in Oakwater Resort. A gated community 4.5 miles away from Disney. Our condo comes fully furnished for all your needs. The PRIMARY SUITE offers an open floor plan with a private EN-SUITE BATH! The 2nd bedroom is bright & has a 2nd FULL BATH. Enjoy a cup of coffee on our SCREENED PATIO. AMENITIES includes POOL, SPA, SPLASH PAD, tennis court, sand volleyball, basketball court, fitness center & game room. Your family will be close to everything!

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 Encore Pool Spa Pets Game Rm Theater Gym
Amazing Brand New Modern Luxurious Home at Encore Resort @ Reunion. PET-FRIENDLY & Minutes to all Theme Parks. BRAND NEW HOME. Private Pool & Spa / Game Room / Movie Theater / Gym / Massage Chair / Fireplace / PS5 / Board Games & Much Much More Embrace the extraordinary and book your stay at our home, where luxury, entertainment come together for an unforgettable vacation experience. ** Please review the rules before booking. Waterpark access is not included. **

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.

Disney Themes Villa | Pool+Gameroom | Near Parks
Escape to Magical Magnolia Manor, a family oasis 10-15 mins from Disney! This unique home features incredible themed rooms (Harry Potter, Star Wars, Lion King) while adults unwind in two luxurious king en suites plus a private, heated pool with no rear neighbors. With 2 king suites and fun beds, for kids, it comfortably sleeps large families up to 8. Enjoy a game room, chef's kitchen, and a serene lanai. Perfect for creating unforgettable memories!

No Airbnb Fee | Newly Renovated 4BR w/ Pool!
**We offer EV Charger for FREE!!! The magic of Orlando starts at home! This incredible house has much more than you need; it has everything you WANT! We offer guests comfort, convenience and an amazing experience!! Transparency and communication is very important to us! We want to make it clear, that we are here at your disposal for any doubts or suggestions. We can't wait to have you here enjoying peace and quiet and having lots of fun!

4BD 2BA Kissimmee Pool House near Disney
This 4BD 2BA house is in a quiet part of Kissimmee less than 5 miles south of Disney! The master suite features a king bed and attached bath with double sinks and walk-in shower. The second room contains a queen bed and the last two rooms have two twins each. There is a fully equipped kitchen and two work spaces, each containing a desk, office chair and computer monitor. Shops, entertainment, and restaurants are just a few minutes away.
Popular amenities for house rentals in Windsor Hills
House rentals with a pool

Luxurious home 2 miles from Disney - Windsor Hill

4 Miles to Disney! Private pool -5 Bedroom Home

6BR Themed Villa | Theater | Pool & Spa with View

10 Min to Disney • Heated Pool • Free Water Park

5BD Formosa Gardens Near Disney (FG 7939)

Best Location! Best Location! Villa in Kissimmee

Fantastic home just 3 miles from Disney World!

Magical Disney Retreat | Pool, Hot Tub & Game Room
Weekly house rentals

Magic Stay near Disney

Magical 3bd Townhome near Disney

Lakeside Magic 5BR Disney Villa w/ Pool & Lakeview

4 m Disney. South Facing, Golf, Pool• Spa• Games

Tiki Palms | Game Room| Heated Pool | Themed

Family Disney Home | Pool | Game Room | Hot Tub

Pet-Friendly Heated Pool with Mini Golf Disney

Disney Retreat | 5BR En-Suite! Pool, Games/Theater
Private house rentals

Fun & Relaxing Oasis | Near Parks + Private Pool

Modern home with Private Pool near Disney

3 Bedroom / 2.5 Bath Townhome (Mins to Disney)

ECR7701 6B Family Disney Vacation @Encore!

Windsor Hills Town Home

Luxury 6BR | Game Room, Outdoor Theater & Pool/Spa

Magic Village Resort Gated Community Disney World

Mario's Arcade Pool House
When is the best time to visit Windsor Hills?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £174 | £174 | £187 | £185 | £163 | £175 | £181 | £166 | £153 | £167 | £185 | £212 |
| 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
- Family-friendly rentals Windsor Hills
- Pet-friendly rentals Windsor Hills
- Rentals with a washing machine and dryer Windsor Hills
- Flat rentals Windsor Hills
- Fitness-friendly rentals Windsor Hills
- Rentals with pools Windsor Hills
- Serviced apartment rentals Windsor Hills
- Rentals with an EV charger Windsor Hills
- Rentals with a patio Windsor Hills
- Rentals with outdoor seating Windsor Hills
- Villa rentals Windsor Hills
- Apartment rentals Windsor Hills
- Rentals with a cinema Windsor Hills
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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Universal's Volcano Bay
- Give Kids the World Village
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Aquatica
- Camping World Stadium
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club




