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Vacation Rentals & Villas in Windsor Hills Resort

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11,376 Houses

Windsor Hills Luxury pool house/2 miles to Disney

Kissimmee house

6 bedrooms / 4 bathrooms / sleeps 13

Responds fast! avg. 1 hour 18 minutes

Price per night from

$241

Wow Factor-Interior Designers Own 5 bed/5bath Home

Kissimmee house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$200

Windsor Hills 5BR/ 5BA SF Pool Villa,3MI to disney

Kissimmee villa

5 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$246

MINUTES TO WALT DISNEY WORLD'S FRONT GATE

Kissimmee condo

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$148

Pooh's Palace in Windsor Hills

Kissimmee villa

5 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 51 minutes

Price per night from

$223

Renting condo,One mile to Disney's Animal Kingdom

Kissimmee condo

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$103

Executive Villa, Pool, Hot tub, WiFi, Games Room

Kissimmee villa

6 bedrooms / 4 bathrooms / sleeps 14

Price per night from

$232

Windsor Hills Retreat Villa

Kissimmee villa

6 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 1 hour 20 minutes

Price per night from

$286

Flagstone Villa

Kissimmee villa

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$259

Windsor Hills Disney Townhouse, Newly Redecorated

Kissimmee townhouse

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 13 minutes

Price per night from

$159

Casa Mickey, Windsor Hills Townhome

Kissimmee townhouse

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$143

Great rentals within 20 miles that match your search

Florida Villa Dreams Come True

Kissimmee villa

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$138

Rivendell Villa Holiday Rental Davenport Orlando

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$126

7 Beds/7 Baths,SOUTH FACING POOL WITH WATER VIEW,ALL NEW FURNITURE,10 MIN. DISNEY

Kissimmee villa

7 bedrooms / 7 bathrooms / sleeps 16

Responds fast! avg. 3 hours 15 minutes

Price per night from

$172

LATE DEALS! AWARD WINNER- Reunion's finest luxury golf front condo.Sunny terrace

Reunion apartment

3 bedrooms / 3 bathrooms / sleeps 6

“This is where to enjoy a week of paradise in Florida.” No stress to check in. You just type in your code and paradise is waiting. Each room is well equipped with luxuries you would expect from a 5 star hotel. Great TV's with lots of movies to choose. Location is great and all the amenities are close by.

Price per night from

$194

Disney, Universal, Beaches, Golf, New Rental

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 55 minutes

Price per night from

$200

Orlando Wyndham Bonnet Creek - Located Close to Di

Orlando apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$315

Disney Fireworks & Lake View 6 Bedroom Premier location in Windsor Hills Resort

Kissimmee villa

6 bedrooms / 4 bathrooms / sleeps 13

Price per night from

$282

Lovely 4BR 3bth Regal Palms Townhouse

Orlando townhouse

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$141

Luxury Resort Villa- 3 miles to Disney- Free Wifi

Four Corners townhouse

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$109

Victorias Villa Upgraded 4 Bed 3 Bath Solar Heated Pool/Spa

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$172

7 Bedroom House on Emerald Island Resort

Four Corners villa

7 bedrooms / 5 bathrooms / sleeps 16

“Stay” Enjoyed every min of the stay. The house was clean from heads to the. The rooms were spacious and enjoyed the quite area

Responds fast! avg. 3 hours 47 minutes

Price per night from

$212

Disney Vacation Condo - stay 6 days get 7th FREE

Four Corners condo

3 bedrooms / 2 bathrooms / sleeps 6

“Owner is awesome. Goes beyond to satisfy guest” This is a 3 bedroom 2 bath unit. Unit has everything you need. It was clean except for the carpets. I called the owner and she asked what did she need to do to make this better. I said clean carpets. She sent Stanley Steamer out to clean them! That was awesome! Loved that we had washer and dryer in the unit. The unit does need some TLC. Deck attached to the master is in need of repair and the bathroom could use and update for sure. We enjoyed our stay and it was very comfortable! Owner is fabulous to work with...best ever!

Price per night from

$80

Awesome House on an Awesome Resort....Orlando area

Haines City house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 36 minutes

Price per night from

$69

Responds fast! avg. 3 hours 41 minutes

Price per night from

$114

⭐Great Deal - 3 Bedrooms Town Home - Near Disney⭐

Kissimmee townhouse

3 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$93

⭐Cozy and Simple 3 Bedrooms - Near Disney World⭐

Kissimmee townhouse

3 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$93

✿Cozy 3 Bedrooms Town Home - Near Disney World✿

Kissimmee townhouse

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$93

Paradise House - Five Star Rated Villa

Kissimmee villa

5 bedrooms / 4 bathrooms / sleeps 10

“The house is very lovely and comfortable.” My family and I enjoyed our stay. The house was spacious and accommodated the adults and children with equal ease. There was one minor glitch, and that was the cable was down for one and a half days, but the management corrected the problem.

Responds fast! avg. 22 minutes

Price per night from

$139

Oakwater Townhome Close To Disney

Kissimmee townhouse

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 42 minutes

Price per night from

$114

⭐Affordable & Good Location 4 BR Town Home - Near Disney World⭐

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$117

✧Near to All Orlando Parks and Attractions! - 7BR Spacious Villa✧

Davenport villa

7 bedrooms / 6 bathrooms / sleeps 14

“My stay at Solona” House was very nice! Had w issue with ants. Nd dusty other than that it was worth it. They did what they could to help in any way! Loved the heated pool

Price per night from

$200

Debbie's Florida Retreat a Luxury Vacation Home

Kissimmee house

4 bedrooms / 3 bathrooms / sleeps 8

“Fabulous Stay in Kissimmee” We loved staying at this home. It was so fun for the kids to have a private pool and so convenient for us as parents. The house has everything you need to make the stay easier...including a crockpot and belgian waffle maker. It was a nice distance from DisneyWorld. The only negative was the distance to Universal Studios. We would totally stay at this home again! We loved it! Also, Chad and Debbie are easy to work with and quick to respond and help your stay work well. We had initially booked to come in March 2020 and had to push it back a year due to covid-19. They could not have made the process easier.

Responds fast! avg. 3 hours 56 minutes

Price per night from

$194

Scotty's Luxury Orlando Villa - Snowbirds welcome

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$172

Disney Vacation Villa 5 br/3 ba (pool, game room)

Davenport villa

5 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$155

✧Near to All Orlando Parks and Attractions! - 4BR Cozy Town Home✧

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$94

✧Simple yet Comfortable 3 BR Town Home - Miles to Disney World✧

Kissimmee townhouse

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$93

⭐Simple yet Comfortable 4 Bedrooms at Coral Cay Resort⭐

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$94

Viewing 38 of 11,376
rentals in Windsor Hills Resort

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Top Destination reviews

Windsor Hills 5BR/ 5BA SF Pool Villa,3MI to disney
we loved this house didn't want to leave

The house was fully stocked for a large family. Loved the location. Had plenty to do on site. House was clean. We felt safe being in a gated security resort. Loved the pool and hot tub after long days at the parks. Jennifer was very helpful and responsive to all my questions before we arrived to the property. Would not hesitate to rent again. Cons on property the strollers we were going to use were broken, maybe could use some new frying pans.Some of the screens on the screened in patio was missing and the patio door the track seemed bent it was hard to close.Just those few things that were minor did not really affect our stay too much.see more
Renting condo,One mile to Disney's Animal Kingdom
Christmas Vaca

The location waa excellent just a 5 minute drive from Disney the apartment was clean and nicely decorated.There was no soap or extra toiletries so bring your own..Booking was easy..The only problem was when we arrived I was emailed the gate code and door code which were both wrong luckily the emergency number was readily available..The next day the door code was changed to something else again but we were quickly texted back with a workable code..Other than that the Stay was great!see more

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