Resorts in Windsor Hills, FL: Compare 10+ Sites & Save

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568 Best Resorts in Windsor Hills (Starting from $62)

Orlando Disney -Windsor hills Resort Condo
Orlando Disney -Windsor hills Resort Condo
Resort
Orlando, FL, USA
0.4k from Windsor Hills center

Hot Tub, Pool, Air Conditioner, Security/Safety, Internet, View, Sports/Activities

6.5

Good

2 reviews

$142
Average price / night
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Disney 2 miles w/Heated Pool, water park, basketball tennis courts,  game room
Disney 2 miles w/Heated Pool, water park, basketball tennis courts, game room
Resort
Kissimmee, FL, 34747, United States
0.4k from Windsor Hills center

AC, Balcony, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Hot Tub

9.0

Fabulous

28 reviews

$179
Average price / night
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Hilton Vacation Club Mystic Dunes Orlando
Hilton Vacation Club Mystic Dunes Orlando
Resort
Orlando, FL, USA
0.6k from Windsor Hills center

Cheap, Accommodations, Pools, Resorts, Parking, Golf, Romantic, Hilton , 3-star

8.9

Fabulous

2486 reviews

$128
Average price / night
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Two Bedroom Deluxe Villa at Westgate Town Center Resort
Two Bedroom Deluxe Villa at Westgate Town Center Resort
Resort
Kissimmee, FL, 34747, United States
0.5k from Windsor Hills center

AC, Arcade, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

New to Booking
$406
Average price / night
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Westgate Grand Villa
Westgate Grand Villa
Resort
Orlando, FL, USA
0.7k from Windsor Hills center

Accommodations, Resorts, Lodgings, Jacuzzis, Places to stay, Family

New to Booking
$191
Average price / night
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*Pixie Dust Penthouse*  Totally Remodeled, Luxury 4th floor Condo
*Pixie Dust Penthouse* Totally Remodeled, Luxury 4th floor Condo
Resort
KISSIMMEE, FL, 34747, United States
0.5k from Windsor Hills center

AC, Balcony, Crib, Dryer, Elevator, Free Parking, Heater, Hot Tub, Internet

10.0

Exceptional

7 reviews

$246
Average price / night
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Summerville Vacation Resort
Summerville Vacation Resort
Resort
Orlando, FL, USA
0.8k from Windsor Hills center

Accommodations, Pools, Resorts, Parking, Pet-friendly, Lodgings, Hot tubs, Places to stay, Family

7.3

Good

32 reviews

$365
Average price / night
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Westgate Town Center 15 Pools on property, restaurants, Ship Wreck Island
Westgate Town Center 15 Pools on property, restaurants, Ship Wreck Island
Resort
Kissimmee, FL, 34747, United States
0.5k from Windsor Hills center

AC, Arcade, Balcony, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet

8.0

Good

1 reviews

$397
Average price / night
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Westgate Vacation Villas Resort
Westgate Vacation Villas Resort
Resort
Windsor Hills, Kissimmee, Florida, USA
0.8k from Windsor Hills center

Cheap, Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, 3-star, Lodgings

8.7

Fabulous

54 reviews

$114
Average price / night
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Experience magic, just a 9-min drive away from Walt Disney World
Experience magic, just a 9-min drive away from Walt Disney World
Resort
Kissimmee, FL, 34747, United States
0.5k from Windsor Hills center

AC, Arcade, Balcony, Dryer, Elevator, Extra Bed, Fitness Equipment, Free Parking, Heater

10.0

Exceptional

1 reviews

$178
Average price / night
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Magical 4BR Escape - Pet-Friendly, 9 Min to Disney
Magical 4BR Escape - Pet-Friendly, 9 Min to Disney
Resort
Orlando, FL, USA
0.9k from Windsor Hills center

Accommodations, Pools, Parking, Resort villages, Lodgings, Jacuzzis, Places to stay, Family

New to Booking
$165
Average price / night
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Luxury Getaway at Westgate Resort, short distance to Disney Parks and Sea World!
Luxury Getaway at Westgate Resort, short distance to Disney Parks and Sea World!
Resort
Kissimmee, FL, 34747, United States
0.5k from Windsor Hills center

AC, Arcade, Balcony, Dryer, Elevator, Extra Bed, Fitness Equipment, Free Parking, Hot Tub

New to Booking
$254
Average price / night
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Westgate Town Center Resort
Westgate Town Center Resort
Resort
Orlando, FL, USA
0.9k from Windsor Hills center

Accommodations, Resorts, Parking, Pet-friendly, Lodgings, Hot tubs, Places to stay, Family

New to Booking
$114
Average price / night
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Traditional Room - Great Experience at Westgate Vacation Villas
Traditional Room - Great Experience at Westgate Vacation Villas
Resort
Kissimmee, FL, 34747, United States
0.5k from Windsor Hills center

AC, Dryer, Internet, Laundry, Pool, Washer

New to Booking
$372
Average price / night
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2 BEDROOM FAMILY RESORT CLOSE TO DISNEY, CHRISTMAS IN FLORIDA
2 BEDROOM FAMILY RESORT CLOSE TO DISNEY, CHRISTMAS IN FLORIDA
Resort
Kissimmee, FL, 34747, United States
0.5k from Windsor Hills center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Laundry

New to Booking
$315
Average price / night
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Grand 2 Bedroom Combo \nGrand 1 Bedroom Lock-Off\nTraditional 1 Bedroom Lock-Off
Grand 2 Bedroom Combo \nGrand 1 Bedroom Lock-Off\nTraditional 1 Bedroom Lock-Off
Resort
Kissimmee, FL, 34747, United States
0.6k from Windsor Hills center

AC, Dryer, Fitness Equipment, Internet, Laundry, No Smoking, Washer

New to Booking
$328
Average price / night
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Westgate Towers Resort
Westgate Towers Resort
Resort
Windsor Hills, Kissimmee, Florida, USA
1.5k from Windsor Hills center

Cheap, Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, 3-star, Lodgings

8.2

Very Good

86 reviews

$79
Average price / night
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Grand 1 BR with jacuzzi tub. Fourteen pools, minigolf, bike rentals and more.
Grand 1 BR with jacuzzi tub. Fourteen pools, minigolf, bike rentals and more.
Resort
Kissimmee, FL, 34747, United States
0.6k from Windsor Hills center

AC, Balcony, Dryer, Fitness Equipment, Heater, Internet, Kitchen, Laundry, No Smoking

New to Booking
$307
Average price / night
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Orbit One Vacation Villas
Orbit One Vacation Villas
Resort
Orlando, FL, USA
1.6k from Windsor Hills center

Cheap, Accommodations, Pools, Resorts, Parking, 3-star, Lodgings, Hot tubs, Places to stay

9.2

Superb

518 reviews

$126
Average price / night
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Spacious 4-bedroom resort with WiFi, AC in lovely Kissimmee
Spacious 4-bedroom resort with WiFi, AC in lovely Kissimmee
Resort
Kissimmee, FL, 34747, United States
0.6k from Windsor Hills center

AC, Dryer, Fitness Equipment, Heater, Internet, Laundry, No Smoking, Washer

New to Booking
$414
Average price / night
Check Availability
Kompose Boutique Resort @ Theme Parks
Kompose Boutique Resort @ Theme Parks
Resort
Orlando, FL, USA
1.7k from Windsor Hills center

Cheap, Accommodations, Pools, Resorts, Parking, Pet-friendly, Lodgings, Hot tubs, Places to stay

9.2

Superb

1455 reviews

$120
Average price / night
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Westgate Resorts, 1 bedroom with kitchenette, minutes away from Disney World.
Westgate Resorts, 1 bedroom with kitchenette, minutes away from Disney World.
Resort
Kissimmee, FL, 34747, United States
0.6k from Windsor Hills center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Laundry, Microwave

New to Booking
$123
Average price / night
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Magic Village Yards Trademark Collection by Wyndham
Magic Village Yards Trademark Collection by Wyndham
Resort
Orlando, FL, USA
1.8k from Windsor Hills center

Accommodations, Pools, Resorts, Parking, Romantic, 4-star, Lodgings, Hot tubs, Places to stay

8.7

Fabulous

317 reviews

$253
Average price / night
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2BR Villa, Beautiful heated pool & Jacuzzi!  Just minutes from all attractions.
2BR Villa, Beautiful heated pool & Jacuzzi! Just minutes from all attractions.
Resort
Kissimmee, FL, 34747, United States
0.7k from Windsor Hills center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

10.0

Exceptional

2 reviews

$329
Average price / night
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Holiday Inn Resort Kissimmee by the Parks by IHG
Holiday Inn Resort Kissimmee by the Parks by IHG
Resort
Orlando, FL, USA
2.0k from Windsor Hills center

Accommodations, Pools, Resorts, Parking, Holiday inn , Pet-friendly, 3-star, Lodgings, Places to stay

7.5

Good

3104 reviews

$89
Average price / night
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Cozy 1-Bedroom Resort Condo, Minutes from Disney, with Waterpark and more
Cozy 1-Bedroom Resort Condo, Minutes from Disney, with Waterpark and more
Resort
Kissimmee, FL, 34747, United States
0.7k from Windsor Hills center

AC, Balcony, Fitness Equipment, Heater, Internet, Kitchen, Microwave, No Smoking, Patio

New to Booking
$153
Average price / night
Check Availability
Maingate Lakeside Resort
Maingate Lakeside Resort
Resort
Orlando, FL, USA
2.1k from Windsor Hills center

Accommodations, Pools, Resorts, Parking, 3-star, Lodgings, Places to stay, Family, Accessible hotels

3.8

Review score

1298 reviews

$62
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Resorts in Windsor Hills.

Stay Near Windsor Hills's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Windsor Hills Resorts on the Map

Frequently Asked Questions

You can explore 568 verified resorts in Windsor Hills. These include a range of options such as beachfront resorts, mountain retreats, and all-inclusive stays designed for a more immersive vacation experience.

Resort prices in Windsor Hills vary depending on the season, property type, and included experiences. Rates typically start from around $62 per night, with higher prices for all-inclusive packages or premium resort properties.

Many resorts in Windsor Hills offer on-site activities such as Pool, Laundry, and Child Friendly. These features allow guests to enjoy dining, entertainment, and recreation without needing to leave the property.

Yes, some resorts in Windsor Hills offer all-inclusive packages where meals, drinks, and select activities are included in the rate. This option can simplify planning and provide a more predictable overall cost for your stay.

For popular travel periods such as holidays or peak seasons, booking 90 to 120 days in advance is recommended to secure the best options. During quieter periods, you may find more availability closer to your travel dates.

Yes, some resorts in Windsor Hills welcome pets. Currently, 17 listings allow pets, although policies may vary. It’s helpful to review property details to understand any restrictions or additional fees.

A hotel typically focuses on accommodation, while a resort offers a wider range of on-site amenities such as dining, entertainment, and recreational activities. Resorts are often designed to provide a more complete, stay-on-property experience.