Windsor Hills Vacation Packages
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Top Windsor Hills vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Alhambra Villas
Solivita
9.2/10 Wonderful! (1,001 reviews)
Aug 6 - Aug 10
4 night stay
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Breeze Airways • Non-stop • Coach
Orlando (MCO) to Newark Liberty Intl. Airport (EWR)
Frontier Airlines • Non-stop • Coach
Price was $426, price is now $310 per person
$310
per person
found 16 hours ago
Very bad internet service. Bad shower / tub setup which can lead to leaks onto the floor and slippery conditions. Need a longer gooseneck or overhead shower head - a simple fix from Home Depot or Lowes. Need more electrical connections - one near the AC but almost unreachable and one in the bathroom. The one on the nightstand was dysfunctional or not plugged into anything. Simple fixes but do not believe anything will happen because of this review. Disappointed that this place carries the name and philosophy of Hilton.
Reviewed on Mar 20, 2025
4.0-star property
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
9.2/10 Wonderful! (1,006 reviews)
Sep 20 - Sep 27
7 night stay
Boston (BOS) to Orlando (MCO)
Delta • Coach
Orlando (MCO) to Boston (BOS)
Frontier Airlines • Coach
Save 100% on your flight
Price was $2,098, price is now $1,176 per person
$1,176
per person
found 1 day ago
This place is amazing! I just wish we had more time to enjoy the resort.
Reviewed on Apr 1, 2026
3.0-star property
Encantada Resort Vacation Townhomes by IDILIQ
8.4/10 Very Good! (1,449 reviews)
Sep 19 - Sep 26
7 night stay
New York (NYC) to Orlando (MCO)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $622, price is now $360 per person
$360
per person
found 19 hours ago
Check in with Security not positive.. we got in, but only after repeated attempts to get the correct unit door access code.
Check out crazy. Arranged "late" check out upon check in. Useless effort...at 10:00 am sharp front desk staff came to unit to demand we leave. Called constantly asking when would we be out. We left earlier than the agreed/approved 1:00 "late" check out staff charged a $70 late check out fee. Other than the staff, the unit was large, clean and nicely furnished.
Reviewed on May 25, 2026
2.0-star property
Seasons Florida Resort
9/10 Wonderful! (3,647 reviews)
Sep 20 - Sep 27
7 night stay
Boston (BOS) to Orlando (MCO)
Delta • Coach
Orlando (MCO) to Boston (BOS)
Frontier Airlines • Coach
Save 100% on your flight
Price was $841, price is now $492 per person
$492
per person
found 1 day ago
Air conditioning LOUD. Works ok. clean room
Reviewed on Jun 1, 2026
5.0-star property
The Bear's Den Resort Orlando
Reunion
7.8/10 Good! (24 reviews)
Sep 13 - Sep 19
6 night stay
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Delta • Non-stop • Coach
Orlando (MCO) to Newark Liberty Intl. Airport (EWR)
Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $3,104, price is now $2,036 per person
$2,036
per person
found 1 day ago
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
$552 nightly
The price is $617 total per night
$617 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.
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 a garden.
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
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
$34
per adult
92% of travellers recommend
Drawn to Life presented by Cirque du Soleil and Disney
$85
per adult
96% of travellers recommend