
House holiday rentals in Windsor Hills
Find and book unique houses on Airbnb
Top-rated house rentals in Windsor Hills
Guests agree: these houses are highly rated for location, cleanliness and more.

4BD 2BA 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, double sinks and walk-in shower. The second room has a queen bed and the last two rooms have two twins each. The eat-in kitchen overlooks the pool, and the separate dining area is equipped with a desk, office chair and computer monitor. The enclosed pool area exits directly onto a park with a walking trail. Shops, entertainment, and restaurants are just a few minutes away.

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!

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!

★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

Resort 2 bedroom Townhome near Disney World

3 BR Private Pool Home 5 miles from Disney

Magical 3bd Townhome near Disney

Fun in Paradise: Pool Villa near Attractions!

ReDesigned | Windsor Hills | Location | Water Park

Fantastic home just 3 miles from Disney World!

Luxury Vacay Home w/ Pool 5Br/5Bath near Disney

Private Epcot-Themed Near Disney
Weekly house rentals

Disney Luxury 5bedroom 4bath Resort WaterPark Free

4 Miles to Disney! Private pool -5 Bedroom Home

5BD Formosa Gardens Near Disney (FG 7939)

Themed 6BR | Game Room | Private Pool & Spa w/View

Cozy Home close to Disney with a Heated pool!

New! Epic Dream House with Pool

Windsor Hills Town Home

Pet-Friendly Heated Pool with Mini Golf Disney
Private house rentals

Fun & Relaxing Oasis | Near Parks + Private Pool

10 Min to Disney • Heated Pool • Free Water Park

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

Modern home with Private Pool near Disney

3 Bedroom / 2.5 Bath Townhome (Mins to Disney)

Windsor Hills Pool Home, Game Room, Walk to Resort

Disney Southfield Getaway!

Magic Village Resort Gated Community Disney World
When is the best time to visit Windsor Hills?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £173 | £173 | £186 | £184 | £163 | £174 | £180 | £166 | £152 | £166 | £184 | £211 |
| 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
- House rentals Four Corners
- House rentals Osceola County
- House rentals Florida
- House rentals United States
- 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




