Welcome to Windsor Hills, a gem in Florida that shines with possibilities. With 2,002 villas to choose from, your perfect vacation is just a click away.

In Windsor Hills, villas range from rustic hideaways to luxurious sanctuaries. Prices start at $85 and can go up to $4,636. Top features often include Pool, offering a unique stay.

Top Features: Pool, Air conditioner, Internet / Wifi, Kitchen or Kitchenette and Laundry

Local Highlights: Disney Springs, Universal CityWalk Orlando, Dolphin Theater, Soarin' Around the World and Avatar Flight of Passage

Begin your journey in Windsor Hills today! Reserve your villas and dive into the beauty and culture of Florida.

Top villas in Windsor Hills

Dining area
8.9 / 10.0
Excellent(27 Ratings)
Olivia's Dream Villa on WindsorHills
Villa
 in Orlando
Garden · Pool · Kitchen or Kitchenette

This Villa for $171 in Windsor Hills, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
booking logo
View deal
Property view
7.8 / 10.0
Very good(17 Ratings)
Windsor Hills Resort 5BR Villa, Amenities, Private Pool & Water Park, Near Disney, Sea World, Universal
Villa
 in Orlando
Garden · Pool · Kitchen or Kitchenette

This attractive Villa in Windsor Hills, $173 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
booking logo
View deal
Facade/entrance
5.0 / 10.0
Fair (2 Ratings)
Flagstone Villa
Villa
 in Orlando
Garden · Pool · Kitchen or Kitchenette

Looking for a memorable stay in Windsor Hills? Our Villa might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.

$$$$
booking logo
View deal
Patio, BBQ facilities, BBQ facilities, TV and multimedia, Dining area, Swimming pool, Swimming pool
No ratings yet
Lilo's Paradise in Windsor Hills
Villa
 in Orlando
Pool · Kitchen or Kitchenette · Air conditioner

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Windsor Hills, at $177 per night for your next great vacation.

$$$$
booking logo
View deal
Facade/entrance
No ratings yet
My Disney Castle
Villa
 in Orlando
Garden · Pool · Kitchen or Kitchenette

Are you ready to indulge in a relaxing getaway? Our Villa in Windsor Hills has everything you need for a rejuvenating stay. Treat yourself to My Disney Castle's exceptional amenities, such as Air conditioner, Dishwasher and Internet / Wifi.

$$$$
booking logo
View deal
New to VacationRenter
Property view
No ratings yet
Magical 6BR Family Retreat with Pool Near Disney
Villa
 in Orlando
Pool · Kitchen or Kitchenette · Air conditioner

This Villa for $172 in Windsor Hills, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
booking logo
View deal
Villa | 6 bedrooms
No ratings yet
This Amazing 6 Bedroom Property With a Lake View
Villa
 in Kissimmee
Pool · Kitchen or Kitchenette · Internet / Wifi

Are you ready to indulge in a relaxing getaway? Our Villa in Windsor Hills has everything you need for a rejuvenating stay. Treat yourself to This Amazing 6 Bedroom Property With a Lake View's exceptional amenities, such as Internet / Wifi, Hot tub or spa and Kitchen or Kitchenette.

$$$$
expedia logo
View deal
Start earning One Key rewards
Indoor pool, outdoor pool
9.9 / 10.0
Outstanding(223 Ratings)
Disney Five Star Pool Villa Home at Windsor Hills
Villa
 in Kissimmee
8 guests · 4 bedrooms · 4 baths
Pool · Kitchen or Kitchenette · Air conditioner

When traveling to Windsor Hills, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $286 per night.

$$$$
vrbo logo
View deal
Villa | 6 bedrooms
No ratings yet
This Amazing 6 Bedroom Property With a Lake View
Villa
 in Kissimmee
2 guests
Pool · Kitchen or Kitchenette · Internet / Wifi

Business stays, family stays, couples stay, getaway vacation, and rental in Windsor Hills at This Amazing 6 Bedroom Property With a Lake View for $193 for your next trip.

$$$$
hotelscom logo
View deal
Villa | 3 bedrooms
No ratings yet
Beautiful 3 bed Townhome in Windsor Hills Resort
Villa
 in Kissimmee
2 guests
Pool · Internet / Wifi

This inviting Villa in Windsor Hills can fit your needs for many types of vacations, at $124 per night.

$$$$
hotelscom logo
View deal
Property view
No ratings yet
Newly Upgraded Disney Themed Vacation Retreat
Villa
 in Orlando
Pool · Kitchen or Kitchenette · Air conditioner

Experience vacation in Windsor Hills with our Villa, Newly Upgraded Disney Themed Vacation Retreat. Enjoy amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
booking logo
View deal
Aerial view
No ratings yet
2538 Windsor Hills
Villa
 in Kissimmee
2 guests
Pool · Kitchen or Kitchenette · Air conditioner

Looking to create some memories in Windsor Hills? Look no further than our Villa, 2538 Windsor Hills. Enjoy top-rated amenities including Air conditioner, Dishwasher and Kitchen or Kitchenette, and more.

$$$$
hotelscom logo
View deal

Villas with a pool in Windsor Hills

Property view
No ratings yet
Windsor Hills Resort Pool Villa Near Disney
Villa
 in Orlando
Pool · Kitchen or Kitchenette · Air conditioner

Discover the beauty of Windsor Hills with a stay at Windsor Hills Resort Pool Villa Near Disney, a top rated Villa with amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
booking logo
View deal
Property view
8.4 / 10.0
Excellent(5 Ratings)
Windsor Galaxy 5 bed/5 bath pool home near Disney
Villa
 in Orlando
Garden · Pool · Kitchen or Kitchenette

This attractive Villa in Windsor Hills, $173 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
booking logo
View deal
Property view
No ratings yet
Entire Home 6 Bedroom 4 Bath, Pool & Spa Disney
Villa
 in Orlando
Pool · Pets allowed · Kitchen or Kitchenette

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Windsor Hills, at $171 per night for your next great vacation.

$$$$
booking logo
View deal
Property view
No ratings yet
Entire Home 6 Bedrooms Pool & Spa Near Disney
Villa
 in Orlando
Pool · Pets allowed · Kitchen or Kitchenette

Looking for the perfect place to call home during your trip to Windsor Hills? This Villa offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
booking logo
View deal
Villa | 4 bedrooms
No ratings yet
Windsor Hills Resort - Pool Spa - Games Room
Villa
 in Kissimmee
2 guests
Pool · Internet / Wifi · Parking

Enjoy the best of Windsor Hills in our Villa, Windsor Hills Resort - Pool Spa - Games Room. A stunning property with amenities including Internet / Wifi, Parking and Pool, and more.

$$$$
hotelscom logo
View deal
Game Room
No ratings yet
Luxurious 6BR/4BA Home w/ Game Room and Private pool Windsor Hills Resort
Villa
 in Orlando
Garden · Pool · Kitchen or Kitchenette

This attractive Villa in Windsor Hills, $173 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
booking logo
View deal
Swimming pool
7.0 / 10.0
Good(1 Rating)
2527 - 3Q/3B c/piscina 10min *Disney Springs*
Villa
 in Orlando
Garden · Pool · Kitchen or Kitchenette

Discover the beauty of Windsor Hills with a stay at 2527 - 3Q/3B c/piscina 10min *Disney Springs*, a top rated Villa with amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
booking logo
View deal
Villa, 6 Bedrooms | Pool | A heated pool
No ratings yet
This amazing 6 Bedroom property with a lake view Villa by RedAwning
Villa
 in Kissimmee
2 guests
Pool · Internet / Wifi · Parking

This attractive Villa in Windsor Hills, $265 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
hotelscom logo
View deal
Property view
No ratings yet
WH7742CS - Newly renovated villa in Windsor Hills
Villa
 in Orlando
Pool · Kitchen or Kitchenette · Air conditioner

Looking for a Villa in Windsor Hills, this Villa for $171 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

$$$$
booking logo
View deal
Property view
No ratings yet
Modern Oasis 6 Bed 4 Bath Long Patio With A View!
Villa
 in Orlando
Pool · Kitchen or Kitchenette · Air conditioner

Soak up the beauty of Windsor Hills in our Villa, Modern Oasis 6 Bed 4 Bath Long Patio With A View!. With a range of amenities such as Air conditioner, Dishwasher and Internet / Wifi, you'll feel right at home.

$$$$
booking logo
View deal
Villa | 3 bedrooms
2.0 / 10.0
Terrible(1 Rating)
3 BR 2 Miles to Disney Pool Free Wifi and More
Villa
 in Kissimmee
2 guests
Pool · Internet / Wifi

Indulge in a peaceful retreat at 3 BR 2 Miles to Disney Pool Free Wifi and More, our elegant Villa in Windsor Hills. Enjoy amenities including Internet / Wifi and Pool, and more.

$$$$
hotelscom logo
View deal
Hot Tub
10.0 / 10.0
Outstanding(3 Ratings)
Luxury Disney Villa 5BR With Private Pool and Spa (4 Miles from Disney)
Villa
 in Orlando
Pool · Kitchen or Kitchenette · Air conditioner

This inviting Villa in Windsor Hills can fit your needs for many types of vacations, at $173 per night.

$$$$
booking logo
View deal

Discover deals on villas in popular destinations

Amelia Island villa rentals
Anna Maria Island villa rentals
Bay County villa rentals
Bay Lake villa rentals
Boca Raton villa rentals
Bonita Springs villa rentals
Boynton Beach villa rentals
Cape Coral villa rentals
Collier County villa rentals
Coral Gables villa rentals
Dania Beach villa rentals
Davie villa rentals
Deerfield Beach villa rentals
Destin villa rentals
Duck Key villa rentals
Dunedin villa rentals
Englewood villa rentals
Florida Keys villa rentals
Fort Lauderdale villa rentals
Fort Myers Beach villa rentals
Four Corners villa rentals
Golden Glades villa rentals
Haines City villa rentals
Holmes Beach villa rentals
Hutchinson Island villa rentals
Jacksonville villa rentals
Key West villa rentals
Kissimmee villa rentals
Lauderdale-by-the-Sea villa rentals
Lee County villa rentals
Little Gasparilla villa rentals
Loughman villa rentals
Marathon villa rentals
Marco Island villa rentals
Merritt Island villa rentals
Miami villa rentals
Miami Beach villa rentals
Miramar Beach villa rentals
North Miami villa rentals
North Miami Beach villa rentals
North Naples villa rentals
Oakland Park villa rentals
Ojus villa rentals
Orlando villa rentals
Osceola County villa rentals
Palm Island villa rentals
Panama City Beach villa rentals
Perdido Key villa rentals
Poinciana villa rentals
Polk County villa rentals
Pompano Beach villa rentals
Rotonda West villa rentals
Sanibel Island villa rentals
Sarasota villa rentals
Siesta Beach villa rentals
Siesta Key villa rentals
South Walton County villa rentals
St Petersburg villa rentals
Sunnyside villa rentals
Tampa villa rentals
Tampa Bay villa rentals
The Villages villa rentals
Venice villa rentals
West Palm Beach villa rentals
Windsor Hills villa rentals
Wellington villa rentals
Indian Shores villa rentals
Hollywood villa rentals
Wildwood villa rentals
Davenport villa rentals
North Port villa rentals
Lely Resort villa rentals
Pembroke Pines villa rentals
Wilton Manors villa rentals
Delray Beach villa rentals
Largo villa rentals
Bradenton villa rentals
Rotonda Lakes villa rentals
East Naples villa rentals
Port Saint Lucie villa rentals
Manasota Key villa rentals
Hernando villa rentals
Hallandale Beach villa rentals
Plantation villa rentals
Sunrise villa rentals
Palm Beach Gardens villa rentals
Islamorada villa rentals
Naples Park villa rentals
Cape Canaveral villa rentals
Indian Rocks Beach villa rentals
Melbourne villa rentals
North Bay Village villa rentals
Key Largo villa rentals
Coconut Grove villa rentals
Florida villa rentals
Riviera Beach villa rentals
Cudjoe Key villa rentals
Estero Island villa rentals
Doctor Phillips villa rentals
Longboat Key villa rentals
South Gulf Cove villa rentals
New Smyrna Beach villa rentals
Miami Shores villa rentals
Homosassa villa rentals
Biscayne Park villa rentals
Jupiter villa rentals
Hillsboro Beach villa rentals
Miami Gardens villa rentals
South Venice villa rentals
Hialeah villa rentals
Hollywood Beach villa rentals
Lake Worth villa rentals
Iona villa rentals
Punta Gorda villa rentals
Fort Myers villa rentals
Upper Grand Lagoon villa rentals
Key Colony Beach villa rentals
Lake Buena Vista villa rentals
Kendall villa rentals
Edgewater Gulf Beach villa rentals
Wesley Chapel villa rentals
Bradenton Beach villa rentals
Everglades villa rentals
Tamarac villa rentals
Lower Grand Lagoon villa rentals
Edgewater villa rentals
Ives Estates villa rentals
Palm Harbor villa rentals
Lauderhill villa rentals
Cocoa Beach villa rentals
Saint Pete Beach villa rentals
Anastasia Island villa rentals
Lehigh Acres villa rentals
Nokomis villa rentals
Surfside villa rentals
Lower Matecumbe Key villa rentals
Brickell villa rentals
Fort Pierce villa rentals
Indian River villa rentals
Isla del Sol villa rentals
Reunion villa rentals
Naples villa rentals
Pensacola Beach villa rentals

Travel inspiration

Keep exploring