
House holiday rentals in Windsor Hills
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Top-rated house rentals in Windsor Hills
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Lakeside Paradise, 15 min Disney + Saltwater Pool
Welcome to Lakeside Paradise – Discover the perfect blend of tranquility and excitement at Lakeside Paradise. Enjoy the serenity of our lakeside retreat, just moments from Central Florida’s top attractions: Disney Parks – 8 miles (15 mins) Universal Studios – 16 miles (25 mins) SeaWorld – 13 miles (20 mins) ESPN Sports Complex – 6 miles (10 mins) Margaritaville/Island H2O – 3 miles (10 mins) Walmart/Target – 6 miles (10 mins) Optional heated pool and spa available for an added fee of $40/day

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!

★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!

Glamorous and Modern House 8 minutes to Disney
The house where your dreams come true, really close to Disney located in the gated Magic Village Resort. This house was practically built and decorated to offer the highest quality services our guests. This 4 bedrooms (all with private bathrooms attached) + 1 social bathroom house has everything you will need for a comfortable stay with your family & friends. It has modern appliances, furniture and BBQ/Grill the latest generation, with comfortable spaces and free Wi-Fi Internet.

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.

Manor on Knottingham Near Disney
Welcome to "Manor on Knottingham," nestled in the heart of Four Corners. The rustic charm, adorned with vintage Disney-inspired decor, transports guests to a bygone era of beloved characters and timeless tales. Outside, enjoy the sparkling blue pool and warm summer weather. A great place for family and friends. "Manor on. Knottingham" promises an extraordinary stay, where the magic of Disney and the comfort of a home merge into an unforgettable experience.

10 Min to Disney • Cozy Townhome + Jacuzzi + BBQ
Welcome to our charming and cozy accommodation! Here you will find an elegant and comfortable space, with all the amenities you need to enjoy an unforgettable stay. Our impeccable service and attention to detail will make you feel at home from the moment you walk through the door. You will feel at ease in this modern family property. ✔ 2 Comfortable Bedrooms ✔ Spacious Living Room ✔ Fully Equipped Kitchen ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking

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!

Park Place! 7 Min from Disney, Pool, Theater
Elevate your next getaway at this outstanding 5-bedroom, 3-bathroom home! Nestled in an upscale, gated community, Park Place boasts 2500 sq. ft. of beautiful living space and easily accommodates 10 guests. This home is ideal for families or a small group visiting the magical Orlando area’s countless attractions. Ideally located between theme parks, shops, and restaurants, you're perfectly situated to experience all the area has to offer!

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

Hibiscus Villa w/ themed rooms, game room and pool

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

3 BR Private Pool Home 5 miles from Disney

Disney Themes Villa | Pool+Gameroom | Near Parks

Modern home with Private Pool near Disney

Fun in Paradise: Pool Villa near Attractions!

Private Pool~BabyReady~Princess Playroom~Waterpark

Elegant Lake Villa - Game Room, Pool & Hot Tub!
Weekly house rentals

Disney Luxury 5bedroom 4bath Resort WaterPark Free

Resort 2 bedroom Townhome near Disney World

Disney Area 3BR Pool Home | Family-Friendly

Serene 6BR Retreat | Pool, Lake View, Near Disney

Fantastic home just 3 miles from Disney World!

Cozy Home close to Disney with a Heated pool!

Pet-Friendly Heated Pool with Mini Golf Disney

20% OFF! LakeView/Poolside - 1.5 Miles to Disney
Private house rentals

10 min. Disney Parks, Kissimmee.

Luxurious home 2 miles from Disney - Windsor Hill

5BD Formosa Gardens Near Disney (FG 7939)

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

*NEW*Theater, FREE Resort, 3 Kings, 2 mi WDW

Windsor Hills Pool Home, Game Room, Walk to Resort

Windsor Hills Town Home

Windsor Hills Single Level 4BR Home, Pool, GameRm
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
- Fitness-friendly rentals Windsor Hills
- Pet-friendly rentals Windsor Hills
- Rentals with a washing machine and dryer Windsor Hills
- Rentals with pools Windsor Hills
- Villa rentals Windsor Hills
- Rentals with a patio Windsor Hills
- Flat rentals Windsor Hills
- Apartment rentals Windsor Hills
- Family-friendly rentals Windsor Hills
- Rentals with outdoor seating Windsor Hills
- Rentals with a cinema Windsor Hills
- Rentals with a hot tub Windsor Hills
- Rentals with an EV charger 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 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
- Disney's Hollywood Studios
- Camping World Stadium
- ICON Park
- Island H2O Live!
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club




