Windsor Hills Vacation Packages
Book a Stay + Flight or Car to save on your trip
Top Windsor Hills vacation package deals
Price found within the past 48 hours. Click for updated prices.
2.0-star property
Seasons Florida Resort
9/10 Wonderful! (3,664 reviews)
Sep 14 - Sep 18
4 night stay
Detroit (DTW) to Orlando (MCO)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $418, price is now $226 per person
$226
per person
found 1 day ago
The room was very clean and the staff was very nice. We enjoyed our stay in Florida❤️
Reviewed on Jul 8, 2026
4.0-star property
Westgate Vacation Villas Resort
8.2/10 Very Good! (1,979 reviews)
Sep 23 - Sep 30
7 night stay
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Frontier Airlines • Roundtrip • Coach
Price was $767, price is now $311 per person
$311
per person
found 1 day ago
Clean room, not flexible if you want to stay extra nights but great place to stay for vacay!
Reviewed on Jul 7, 2026
3.5-star property
Westgate Towers Resort
8.6/10 Excellent! (1,003 reviews)
Sep 23 - Sep 30
7 night stay
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Frontier Airlines • Roundtrip • Coach
Price was $761, price is now $311 per person
$311
per person
found 1 day ago
This was our 2nd time staying here. Rooms are amazing. Highly recommended.
Reviewed on Jul 5, 2026
4.0-star property
Westgate Palace Hotel / Universal / I-Drive
International Drive District
9/10 Wonderful! (1,275 reviews)
Sep 1 - Sep 6
5 night stay
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Frontier Airlines • Roundtrip • Coach
Price was $1,123, price is now $472 per person
$472
per person
found 1 day ago
Dryer and washer had hair in them poor Internet connection needs extra parking spaces for customers
Reviewed on Jul 8, 2026
3.5-star property
The Delaney Hotel
South Orange
9.6/10 Exceptional! (1,129 reviews)
Sep 14 - Sep 18
4 night stay
Detroit (DTW) to Orlando (MCO)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $720, price is now $398 per person
$398
per person
found 1 day ago
Everyone was very nice! Property was clean. We loved the restaurant attached
Highly recommend!!
Reviewed on Jul 7, 2026
Top rated hotels for your Windsor Hills vacation package
Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear
Kissimmee FL
0.09 mi from Windsor Hills
$522 nightly
The price is $584 total per night
$584 total
Jul 12 - Jul 13
Total with taxes and fees
Guests of this vacation home have access to an outdoor pool, a gym, and a hot tub. Limited parking is available. Other amenities at this family-friendly vacation home include an arcade/game room, laundry facilities, and local meal delivery service.
Pool
Hot Tub
Minutes to the Magic! 3-bedroom home, 6 minutes to Walt Disney World!
Kissimmee FL
0.21 mi from Windsor Hills
Guests of this vacation home have access to an outdoor pool, a gym, and a hot tub. Other amenities at this family-friendly vacation home include an arcade/game room, laundry facilities, and barbecue grills.
Pool
Hot Tub
Villa 2655 - Updated Home w/ Arcade Rm! 3 mi from Disney, Pool Heat, BBQ & PS5
Kissimmee FL
0.03 mi from Windsor Hills
At this vacation home, guests enjoy an outdoor pool, a gym, and a hot tub. Other amenities at this family-friendly vacation home include an arcade/game room, laundry facilities, and local meal delivery service.
Pool
Hot Tub
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Things to do
Drawn to Life presented by Cirque du Soleil and Disney
$85
per adult
96% of travellers recommend
