Middleton Vacations from ￥243,595

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The Latest Middleton Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

￥243,595
per person
Nov 18 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
9.2/10 Wonderful! (1,003 reviews)
We stayed in one of the cottages and it was just perfect. The fully equipped kitchen downstairs with a master suite was perfect for my parents. I appreciated having the laundry upstairs with the other bedrooms. The staff at the main building were so helpful with our packages and printing documents for us. Unfortunately we had a very busy week and could not enjoy the wonderful amenities of the resort. Overall, a great selection and would start again!

Reviewed on Sep 25, 2026

Magic Village Yards, Trademark Collection by Wyndham

Magic Village Yards, Trademark Collection by Wyndham

￥403,595
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
9.2/10 Wonderful! (1,208 reviews)
Overall good! I feel like it needs deeper cleaning On the floor.

Reviewed on Sep 28, 2026

Grand Lake Resort

Grand Lake Resort

￥308,604
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
9.2/10 Wonderful! (253 reviews)
La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks

La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks

International Drive District
￥328,350
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
8.8/10 Excellent! (3,098 reviews)
Convenient affordable location. Very close to SeaWorld.

Reviewed on Oct 1, 2026

Arnold Palmer's Bay Hill Club & Lodge

Arnold Palmer's Bay Hill Club & Lodge

Bay Hill
￥256,244
per person
Nov 18 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
9.2/10 Wonderful! (1,001 reviews)

Find the Best Middleton Vacation Packages

Middleton Hotel Deals

The Waterfront Inn

The Waterfront Inn

1105 Lake Shore Drive The Villages FL
￥15,298
￥16,368 total
Nov 1 - Nov 2
includes taxes & fees
The Waterfront Inn
Brownwood Hotel & Spa

Brownwood Hotel & Spa

3003 Brownwood Blvd Wildwood FL
Fully refundableReserve now, pay when you stay
￥15,586
￥16,677 total
Oct 4 - Oct 5
includes taxes & fees
Brownwood Hotel & Spa
The Citrus on the Lake

The Citrus on the Lake

199 W Ruby Street Tavares FL
Fully refundableReserve now, pay when you stay
￥15,226
￥16,902 total
Oct 26 - Oct 27
includes taxes & fees
The Citrus on the Lake
See all 2,249 properties in Middleton
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.