
Upper Matecumbe Key Vacations from ¥581,778
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The Latest Upper Matecumbe Key Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Hilton Garden Inn Miami Brickell South
Brickell
Price was ¥1,133,066, price is now ¥581,778 per person
¥581,778
per person
Aug 24 - Aug 31
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
7.8/10 Good! (1,001 reviews)
Staff were very friendly and helpful. Location and the fact that the hotel is NOT a high-rise building were huge pluses for me. I purchased a room deal that included the breakfast buffet, which was very good. I didn’t park a vehicle or use the bar so I can’t speak to either of those amenities. The downsides were dirty/ old carpet everywhere in the building and low water pressure in the shower.
Reviewed on Jun 1, 2026

AKA Brickell High Floor Free Parking by Palermo Home
Brickell
Price was ¥1,247,168, price is now ¥648,920 per person
¥648,920
per person
Aug 24 - Aug 31
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.6/10 Excellent! (9 reviews)
Good location with relative value. Did not expect an Air-B&B-Check-in, but get a quick response by phone call. A big suite, with slightly old furniture, some missing parts, like missing washbasin sink cover, a door handle, a missing light bulb etc, could be a concern for a new check-in guest. Generally good for a short stay with cheaper price.
Reviewed on Feb 7, 2026

AKA Brickell 32th Free Parking by Palermo Home
Brickell
Price was ¥1,272,288, price is now ¥664,534 per person
¥664,534
per person
Aug 24 - Aug 31
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
10/10 Exceptional! (3 reviews)
This was an absolutely stunning place to stay! High end accommodations connected to the AKA hotel. Close to the water, great restaurant, the pool was fabulous. Easy to get around to everything in Miami from here. Parking included with this reservation, which was a huge plus. Highly recommend this for anyone staying in Miami whether for a couple or a family of four.
Reviewed on Jul 5, 2025

Roami at The Palace
Midtown
Price was ¥1,162,396, price is now ¥616,457 per person
¥616,457
per person
Aug 24 - Aug 31
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.2/10 Very Good! (33 reviews)
The unit was clean, and check in/out was super easy. The kitchen had dishes, utensils, small pots and pans, a full fridge/freezer, dishwasher, and a portable stove unit. We really appreciated that towels and shampoo/conditioner/lotion were provided as well! Perfect for a budget-friendly trip!
Reviewed on May 20, 2026
Find the Best Upper Matecumbe Key Vacation Packages
Upper Matecumbe Key Hotel Deals

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ¥43,365 per night from Jun 18 to Jun 19
¥43,365
¥60,479 total
Jun 18 - Jun 19
includes taxes & fees
9.2/10 Wonderful! (1,317 reviews)
"Cheeca Lodge is my absolute favorite place in The Keys The property is gorgeous, I love the amenities, the complimentary kayaking, bikes & champagne for Mother’s Day was such a nice touch The rooms are so cozy, just love it there. Ask for Rob at the pool bar, he makes a great drink!"
Reviewed on Jun 4, 2026

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ¥30,796 per night from Jun 18 to Jun 19
¥30,796
¥43,641 total
Jun 18 - Jun 19
includes taxes & fees
9.2/10 Wonderful! (1,738 reviews)
"Pros....Room was awesome and clean. Amazing views. Close to anything you may need. Cons....Property was a little rough. Cans and trash were kind of everywhere."
Reviewed on Jun 3, 2026

Islander Resort
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ¥40,906 per night from Jun 30 to Jul 1
¥40,906
¥56,815 total
Jun 30 - Jul 1
includes taxes & fees
9.4/10 Exceptional! (1,031 reviews)
"Safety issue. All paddleboards were worn with cracks and fiberglass splinters in multiple areas. Can easily cut someone. Was not comfortable to use one. EVERYTHING ELSE FANTASTIC."
Reviewed on Jun 3, 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.
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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.
