
Windsor Vacations from ¥406,672
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The Latest Windsor Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Travelodge by Wyndham Kissimmee/Orlando
Price was ¥544,850, price is now ¥406,672 per person
¥406,672
per person
Apr 30 - May 6
found 12 hours ago
Roundtrip flight included
Tokyo (TYO) to Orlando (MCO)
5.2/10 (402 reviews)
Room was very dated and had cheap in matching fixtures. The pool was clean and nice. No doorknob or lock on the bathroom door. Bed and pillows were comfortable.
Reviewed on Mar 24, 2026

Westgate Towers Resort
Price was ¥613,316, price is now ¥417,952 per person
¥417,952
per person
Apr 30 - May 6
found 12 hours ago
Roundtrip flight included
Tokyo (TYO) to Orlando (MCO)
8.6/10 Excellent! (1,004 reviews)
Hotel rooms are spacious. Right in a rear location. Walmart is 3 min drive, CVS across the street. Hot tbs ar lean, pool is clean. For people who don’t read, there is no room service, have to ask for any extra items.
Reviewed on Mar 25, 2026


Destiny Palms Hotel Maingate West
Price was ¥564,279, price is now ¥413,393 per person
¥413,393
per person
Apr 30 - May 6
found 12 hours ago
Roundtrip flight included
Tokyo (TYO) to Orlando (MCO)
8.4/10 Very Good! (2,298 reviews)
For the price, it is very good. The AC was fairly quiet and effective.Let me tell you, this place was impressively clean — spotless in a way you don’t see very often. You walk in and immediately notice how well everything is taken care of. The staff? Fantastic people, incredibly attentive, and they make you feel like you’re the most important guest in the building.
The rooms were a very solid size, plenty of space to relax without feeling cramped. And the bed — unbelievably soft. The kind of soft where you lie down “just for a minute” and suddenly it’s morning. Truly excellent.
Overall, a strong stay. Clean place, great people, comfortable rooms. Hard to beat.
Reviewed on Mar 27, 2026

Holiday Inn Resort Orlando - Lake Buena Vista by IHG
Price was ¥572,296, price is now ¥427,404 per person
¥427,404
per person
Apr 30 - May 6
found 12 hours ago
Roundtrip flight included
Tokyo (TYO) to Orlando (MCO)
8.4/10 Very Good! (3,842 reviews)
This place was okay. A bit dated, but our room was clean. The coffee maker didn't work and we didn't have blackout blinds on the windows, but I didn't complain about it. The area has some fast-food places, and we enjoyed the Applebees. It's not a very walkable area, however. If you're on a strict budget, this place is fine. I found the staff to be quite pleasant.
Note: the 5pm shuttle to Disney Springs took an hour as it goes to many, many hotels. The 8pm shuttle back took 10 minutes.
Reviewed on Mar 26, 2026
Find the Best Windsor Vacation Packages
Windsor Hotel Deals

HOM Hotel Gainesville, SureStay Collection by Best Western
3905 Sw 43Rd St Gainesville FL
Fully refundableReserve now, pay when you stay
The price is ¥13,650 per night from Apr 5 to Apr 6
¥13,650
¥15,357 total
Apr 5 - Apr 6
includes taxes & fees
8.4/10 Very Good! (1,860 reviews)
Staff belligerent after just one mild criticism. Someone also entered my room & left it OPEN, no less, with “respect privacy” sign on the door. No clear delineation between lobby & breakfasting area for people with dogs. Bathroom super-functional, beds & pillows comfortable.
Reviewed on Mar 27, 2026

Country Inn & Suites by Radisson, Gainesville, FL
4015 Sw 43rd St Gainesville FL
Fully refundable
The price is ¥14,289 per night from Apr 14 to Apr 15
¥14,289
¥16,075 total
Apr 14 - Apr 15
includes taxes & fees
9.2/10 Wonderful! (1,736 reviews)
It's always served me well. I stay here for the Florida Gators football game. Great place and good breakfast.
Reviewed on Mar 27, 2026

DoubleTree by Hilton Gainesville
3726 Sw 40th Blvd Gainesville FL
Fully refundableReserve now, pay when you stay
The price is ¥16,746 per night from Apr 5 to Apr 6
¥16,746
¥18,839 total
Apr 5 - Apr 6
includes taxes & fees
7.8/10 Good! (1,000 reviews)
Decent room clean space, front staff seemed kind of indifferent, just ok, nothing to rave about.
Reviewed on Mar 24, 2026
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.
Discover the most popular places to visit in Windsor

University of Florida
Take a campus tour or just explore the area around University of Florida, a top college in Gainesville. Stroll along the lakeside or attend a sporting event in the area.

Florida Museum of Natural History
You can spend an afternoon exploring the galleries in Florida Museum of Natural History during your trip to Gainesville. You can attend a sporting event while in the area.
Gainesville Raceway
Catch an event at Gainesville Raceway during your trip to Gainesville. Amble around the area's lakeside or attend a sporting event.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
