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
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 17 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
3.0-star property
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
International Drive District
7.8/10 Good! (518 reviews)
Sep 3 - Sep 8
5 night stay
Boston (BOS) to Orlando (MCO)
JetBlue Airways • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $742, price is now $396 per person
$396
per person
found 1 day ago
The staff were amazing, the parking for the hotel was horrible.
Reviewed on Jan 3, 2026
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
4.0-star property
Westgate Lakes Resort & Spa Universal Studios Area
8.4/10 Very Good! (6,584 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 $1,064, price is now $622 per person
$622
per person
found 1 day ago
Everything was average. I chose this hotel because of the kids’ pool and water park, not knowing that access to the water park required an additional charge on top of the stay. This information was not disclosed until our arrival. It would have been helpful to know about these extra fees beforehand, as it may have influenced my decision when choosing this hotel.
Reviewed on May 31, 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
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.
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