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Vacation Rentals & Villas in Windsor Hills Resort

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17,857 Houses

Windsor Hills Luxury pool house/2 miles to Disney

Kissimmee house

6 bedrooms / 4 bathrooms / sleeps 13

Responds fast! avg. 1 hour 53 minutes

Price per night from

$232

5 Star Windsor Hills condo steps from the pool, renovated 2016

Kissimmee condo

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$117

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

Kissimmee house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$206

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

Kissimmee villa

5 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 2 hours 3 minutes

Price per night from

$270

MINUTES TO WALT DISNEY WORLD'S FRONT GATE

Kissimmee condo

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$127

Pooh's Palace in Windsor Hills

Kissimmee villa

5 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 1 hour 8 minutes

Price per night from

$230

Renting condo,One mile to Disney's Animal Kingdom

Kissimmee condo

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$106

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

Kissimmee villa

6 bedrooms / 4 bathrooms / sleeps 14

Price per night from

$185

Windsor Hills Retreat Villa

Kissimmee villa

6 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 22 minutes

Price per night from

$230

Windsor Hills Townhouse, 3 bedrooms, 3 bathrooms

Kissimmee townhouse

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$126

Minion Cove

Kissimmee condo

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$137

Flagstone Villa

Kissimmee villa

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$279

Great rentals within 20 miles that match your search

Amazing views from the pool! Windsor Hills Resort!

Four Corners house

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$207

Luxury Six Bedroom Home - Close to Disneyworld

Four Corners villa

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$201

VISTA CAY. New!POOLSIDE ESCAPE NEAR ALL PARKS, ATTRACTIONS & INTERNATIONAL DRIVE

Orlando apartment

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 1 hour 31 minutes

Price per night from

$288

477-ORLANDO-15 Min FROM DISNEY & OMNI RESORT

Four Corners house

8 bedrooms / 6 bathrooms / sleeps 26

Price per night from

$318

ORLANDO-CHAMPIONS GATE-15 Min FROM DISNEY & OMNI RESORT

ChampionsGate house

4 bedrooms / 1 bathroom / sleeps 11

Price per night from

$117

1580-ORLANDO-15 Min FROM DISNEY & OMNI RESORT

ChampionsGate house

8 bedrooms / 6 bathrooms / sleeps 17

Price per night from

$283

730-ORLANDO-CHAMPIONS GATE-15 Min FROM DISNEY & OMNI RESORT

Four Corners house

4 bedrooms / 1 bathroom / sleeps 11

Price per night from

$117

Luxurious

Orlando apartment

3 bedrooms / 4 bathrooms / sleeps 8

“Absolutly Wonderful!” Best value, best decor, most room for the $ Would have had to pay 3x more for a resort suite of the same size!

Price per night from

$163

1570-ORLANDO-CHAMPIONS GATE-15 Min. da DISNEY & OMNI RESORT-

ChampionsGate house

5 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$151

3 MILES FROM DISNEY / SUN LAKE / 2 BED / 2 BATH/

Kissimmee condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 59 minutes

Price per night from

$117

139 - Luxury 2 Masterbed/bath Unit with Garden View - International Drive

Orlando apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 43 minutes

Price per night from

$221

Stunning 4 bed villa with south facing pool and spa

Davenport house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$141

Sheraton Vistana Fountains II - Timeshare

Kissimmee hotel apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$158

Stunning 7 bedroom Villa Lake Berkley, Private pool and Jacuzzi

Kissimmee house

7 bedrooms / 4 bathrooms / sleeps 14

Price per night from

$211

Unit 25- 3 bedroom Emerald Island 8417

Kissimmee townhouse

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 10 minutes

Price per night from

$104

Marriott Cypress Harbor 2 bedroom sleeps 6

Orlando house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$334

Joy Palace - Luxury new home in Champions Gate, South facing,Disney,Golf

Davenport villa

9 bedrooms / 5 bathrooms / sleeps 24

Responds fast! avg. 2 hours 56 minutes

Price per night from

$333

Pat and Ron's Holiday Home, Relaxing Retreat

Kissimmee villa

3 bedrooms / 2 bathrooms / sleeps 6

“Good” I was a little disappointed this time. I have been going there since 2015. In the past when I had minor problems with the home, the response was quick. This time I called on Saturday to ask about no input message on the tv screen, I was told me they would come on Sunday to check it. They come on Sunday and knocked at 10:30 but we were sleep and did not hear them, so I called again and someone came over in about 1 and 30 minutes. I pointed out that the main bathroom in the hall had a problem with the bathroom and needed to get fixed. He looked at it and said he needed a piece for the door and he would fix it on Monday. I told him people were getting locked up inside. Well I left on 12/18/18 and no one ever came to fix the lock on the door. The clean in the kitchen needed some attention with the over. I did not get a chance to show anyone as no one came back to fix the door. The oven has some spilled grease on the bottom and needed to be cleaned before I got there. These are minor issues with me, that I lived with and had a good time, I would come again. The management should realize that certain things the guests are not responsible for even though it may seem small to them, but it is not small for the renter. I do not have then same cable company that is used where I was, so I did not complain about it when it went off and on and in and out half the day, it is not my fault nor was it the fault of Pat and Ron so I did not complain about it.

Price per night from

$115

Gorgeous, newly refurbished throughout 3 bed 2 bath private pool home

Four Corners villa

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 21 minutes

Price per night from

$164

H9063 Brand New 9B6.5B Poolvilla Minutes to Disney

Four Corners villa

9 bedrooms / 6 bathrooms / sleeps 18

Price per night from

$449

Excellent apartment in Orlando for up to 10 people

Four Corners apartment

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$317

New listing, Modern home, 10 min to disney with private pool

Four Corners villa

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$176

Orlando Vacation Rental Home

Davenport townhouse

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$116

Luxury 3 Bedroom in Orlando

Orlando townhouse

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$158

Excellent spacious apartment in wonderful Resort

Orlando hotel apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$268

Mystic Dunes Resort - Golf, 4 Pools, Lagoon & More

Reunion villa

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$152

Viewing 38 of 17,857
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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