Vacation Rentals & Villas in Windsor Hills Resort

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6,957 Houses

Windsor Hills Luxury pool house/2 miles to Disney

Kissimmee house

6 bedrooms / 4 bathrooms / sleeps 13

Responds fast! avg. 39 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

$224

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

Kissimmee villa

5 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$247

MINUTES TO WALT DISNEY WORLD'S FRONT GATE

Kissimmee condo

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$160

Pooh's Palace in Windsor Hills

Kissimmee villa

5 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 34 minutes

Price per night from

$516

Renting condo,One mile to Disney's Animal Kingdom

Kissimmee condo

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$103

Windsor Hills Retreat Villa

Kissimmee villa

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$458

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

$160

Great rentals within 20 miles that match your search

Sunrise Villa Fabulous Family Villa near to Disney

Davenport villa

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$135

Sandy Ridge Villa

Davenport villa

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$141

Cocoa Villa

Haines City villa

4 bedrooms / 3 bathrooms / sleeps 10

“Vacation to remember” beautiful home, beautiful neighborhood, security guards were very nice, always smiling and greeting us as we enter and exit, The pest control guy was very informative and nice, seems to love his job. The maintenance guy answer questions and followed up on our concerns immediately. Overall I enjoyed our home and would be interested in leasing property out there. Very convenient to all stores and dinning areas

Price per night from

$149

Lovely Mango Keys Home includes WiFi and Hot Tub

Kissimmee house

2 bedrooms / 2 bathrooms / sleeps 5

“Very nice, clean, quite” Was very nice and clean. Maybe the only thing should be te a/c in masterroom wasn't cold. Everything else was very good and enjoyable.

Responds fast! avg. 2 hours 32 minutes

Price per night from

$78

Responds fast! avg. 3 hours 53 minutes

Price per night from

$212

Sanitized, Private Pool, Large Yard for Kids, Wifi, BBQ, Gated Resort Amenities

Orlando villa

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 3 hours 53 minutes

Price per night from

$126

Emerald Villas

Davenport villa

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$189

Sanitized, Private Pool/Spa, Nice View, No Rear Neighbor, Wifi, Gated Resort

Orlando villa

7 bedrooms / 5 bathrooms / sleeps 16

Responds fast! avg. 3 hours 53 minutes

Price per night from

$195

The Seasons Villa, lake view and 4 master bedrooms

Kissimmee villa

6 bedrooms / 6 bathrooms / sleeps 13

“Beautiful home !!!” Everything was so beautiful in this home it was the perfect choice the bedroom all had their own bathroom with the exception of the kid rooms. Owner was very easy to reach and they give you step by step instructions for the home. I loved it ! This will be our go to for our Disney vacations! Stores and restaurants are near by so easy if you want to shop for food or in general.

Responds fast! avg. 2 hours 1 minutes

Price per night from

$230

Golf Resort Private Pool Golf Tennis SPA Villa

Davenport house

12 bedrooms / 6 bathrooms / sleeps 24

Price per night from

$882

2 room Celebration Disney Poolside SPA-Golf

Celebration condo

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$226

Villa by Disney

Davenport villa

3 bedrooms / 2 bathrooms / sleeps 7

“idilic location/ perfect for visiting theme parks” Service from owners fist class. House was exactly as described. Ideal location for theme parks and shopping and eating. Could not get grandkids out the pool they absolutely loved it. 2nd time we have stayed there and will have no hesitation booking again should we go back to Florida.

Responds fast! avg. 1 hour 58 minutes

Price per night from

$128

Palm Heaven Villa, Relaxing Family Getaway in Kissimmee

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$213

High Grove Villa

Clermont villa

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$149

Morning Star Disney Villa

Orlando villa

4 bedrooms / 2 bathrooms / sleeps 8

“We Absolutely Loved It!” We absolutely loved the house- it was well taken care of and plenty of room. Our kids really enjoyed the pool and we appreciate all the pool toys/supplies that were provided. The kitchen was well equipped that we were able to cook meals every day. Thank you SO much! We will definitely be back!

Responds fast! avg. 45 minutes

Price per night from

$132

Disney Family Villa pool/spa/games room, 5 bds 4 bathrooms, 15 Mins to Disney

Kissimmee villa

5 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$199

Highlands Reserve villa :South facing private Pool

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 28 minutes

Price per night from

$206

Beautiful Villa (featuring secluded pool area)

Davenport villa

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$110

Renewed Villa at Regal Palms

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$200

River Island - North - East - West Villages at Orange Lake

Kissimmee villa

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$243

"The Palms" at Lake Davenport

Davenport villa

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 2 hours 4 minutes

Price per night from

$139

4 Bedroom Poolside Sunny Retreat with Fully Inclusive Price.

Kissimmee bungalow

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 22 minutes

Price per night from

$172

Weston Magic in Orlando

Clermont villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 34 minutes

Price per night from

$142

The Orlando Lodge

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

“Fun in the sun” Very nice- with 2 masters, and a nice layout. Clean home with nice pool- the kitchen had only the basics and you will need to provide dish soap, cleaners, TP and garbage bags. Our only issue was parking- be warned, if you have more than one car, you will need to find parking- we had a travel trailer, and didn't know we would not be able to park on the street- we ended up renting a storage space down the road. The neighbors were not very nice about it. Gary was great, and so was his rental management.

Responds fast! avg. 2 hours 35 minutes

Price per night from

$101

Stunning Lakeview Luxury Villa with WiFi and Hot Tub

Kissimmee villa

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$249

Sundown Palm

Kissimmee villa

6 bedrooms / 4 bathrooms / sleeps 13

Responds fast! avg. 15 minutes

Price per night from

$344

Valencia

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$155

Luxury 5 Star Charlotte Harbor Vacation Rental near to Disney, Free WiFi & Calls

Kissimmee villa

6 bedrooms / 4 bathrooms / sleeps 13

Price per night from

$220

Davenport Villa Rental Florida

Davenport villa

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 55 minutes

Price per night from

$122

Highlands Reserve Golf Villa

Davenport villa

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$164

Viewing 38 of 6,957
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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