
Winter Park Vacations from ¥282,514
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The Latest Winter Park Vacation Packages
Price found within the past 48 hours. Click for updated prices.

The Delaney Hotel
South Orange
Price was ¥326,368, price is now ¥282,514 per person
¥282,514
per person
May 11 - May 15
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
9.6/10 Exceptional! (1,063 reviews)
Very welcoming to pets. Excellent staff. Comfortable beds and spacious room and bathroom
Reviewed on Mar 8, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark
Price was ¥415,288, price is now ¥315,028 per person
¥315,028
per person
May 11 - May 15
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
9.2/10 Wonderful! (1,002 reviews)
The big pool was great a nice half of the border is shallow so the little ones have a place to play.
When you reserve the vista cottages you are technically on a different portion of the resort. They only provide 2 garbage bags, 2 dishwasher pods and 1 laundry pouch for 1 load. They do not provide any additional even though you are staying so many days. So please pack those. The shuttle system they participate in is an outside company. It’s one of the cheaper ones. The shuttle is used by like 4-5 hotels so some nights it took 2 hours to get back. The shuttle did not have many options for universal. The Disney one had enough pickups. Ranging from 5:30p, 7:30, 9:30. The guy dropped off in the evening at the bottom of the hill unfortunately he drove the evening bus everyday. Definitely harder after a long day at the parks. The valet doesn’t mind picking you up from the bottom so please remember to call them. The valet was so helpful and informative. They gave us the best places to go. The hotel lets the timeshare at the front door so your greated with sales not hellos. The hotel did Not provide an airport shuttle. I still have the place a 4 because my family enjoyed ourselves we just wish we knew these things prior to booking.
Reviewed on Mar 8, 2026

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
Golden Oak
Price was ¥569,936, price is now ¥482,666 per person
¥482,666
per person
May 11 - May 15
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
9.6/10 Exceptional! (886 reviews)
Amazing pool and grounds! Perfect for our family of four.
Reviewed on Mar 5, 2026

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
International Drive District
Price was ¥438,184, price is now ¥371,200 per person
¥371,200
per person
Apr 28 - May 4
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
7.8/10 Good! (376 reviews)
Overall comfortable stay but the breakfast can use a whole new make over. Add more options for meats and hot foods. Pastries won’t hurt.
Reviewed on Mar 3, 2026

Evermore Orlando Resort
Price was ¥459,917, price is now ¥394,650 per person
¥394,650
per person
May 11 - May 15
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
9.6/10 Exceptional! (573 reviews)
11/10 in every aspect. We had the 4 bedroom flat with the bay view and wow. Probably the first ever place my family has stayed and my wife didn’t take the first hour cleaning everything. The staff is top notch. Helpful in every way and working around the clock. Pools were pristine and warm which I expected but the bay… for such a big piece of water it was spotless. You really feel like you’re in paradise with Disney 10 minutes away. This will be a yearly vacation spot for my family from now on we are hooked on evermore!
Reviewed on Mar 8, 2026
Find the Best Winter Park Vacation Packages
Winter Park Hotel Deals

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
Fully refundableReserve now, pay when you stay
The price is ¥21,974 per night from Apr 10 to Apr 11
¥21,974
¥24,721 total
Apr 10 - Apr 11
includes taxes & fees
9.2/10 Wonderful! (4,821 reviews)
Huge resort, can get lost easily. Suites are bright & roomy. Rooms that are not on ground floor can be difficult to get luggage upstairs (no elevator). Overall nice resort.
Reviewed on Mar 10, 2026

Hyatt Regency Orlando International Airport
9300 Jeff Fuqua Boulevard Orlando FL
Fully refundableReserve now, pay when you stay
The price is ¥31,398 per night from Mar 16 to Mar 17
¥31,398
¥35,324 total
Mar 16 - Mar 17
includes taxes & fees
9.4/10 Exceptional! (4,067 reviews)
The property is located very convenient.
Reviewed on Mar 9, 2026

Universal's Cabana Bay Beach Resort
6550 Adventure Way Orlando FL
Fully refundableReserve now, pay when you stay
The price is ¥21,774 per night from Mar 11 to Mar 12
¥21,774
¥24,495 total
Mar 11 - Mar 12
includes taxes & fees
9/10 Wonderful! (6,441 reviews)
It is always so lovely! Family friendly , they meet characters in the lobby and they have a whole water section for kids. The rooms are amazing! I booked a view of volcano bay and it did not disappoint if you were just staying at the hotel there is much to do,
Reviewed on Mar 10, 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 Winter Park

Walt Disney World® Resort
Walt Disney World® Resort is part of Orlando. It makes up part of bustling metropolis that is home to 240,000 inhabitants. Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando’s city center. If you are flying in, Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando International Airport.

Universal Studios Florida
Movie sets and thrill rides combine to create this internationally acclaimed theme park.

Universal Orlando Resort
Make your Florida vacation one to remember with a stay at this hotel and theme park complex.
What to do in Winter Park

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
¥4,249
per adult
92% of travellers recommend

Universal Orlando Resort Theme Park Tickets
¥25,302
per adult
78% of travellers recommend

Universal Orlando Resort Express Passes
¥29,886
per traveler
82% of travellers recommend
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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.
