Upper Matecumbe Key Vacations from ￥552,435
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The Latest Upper Matecumbe Key Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
Price was ￥2,695,754, price is now ￥1,477,790 per person
￥1,477,790
per person
Sep 10 - Sep 14
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8/10 Very Good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
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 ￥35,332 per night from Aug 9 to Aug 10
￥35,332
￥51,624 total
Aug 9 - Aug 10
includes taxes & fees
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ￥24,838 per night from Aug 18 to Aug 19
￥24,838
￥39,819 total
Aug 18 - Aug 19
includes taxes & fees
8.8/10 Excellent! (1,286 reviews)
"Breathtaking view from our balcony. Large comfortable suite"
Reviewed on Jul 19, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ￥23,795 per night from Aug 16 to Aug 17
￥23,795
￥35,904 total
Aug 16 - Aug 17
includes taxes & fees
9.2/10 Wonderful! (1,745 reviews)
"The property was beautiful and well maintained. The check in staff and staff at the bar were not polite or helpful at all. Very disappointing. The food selection at 3 oclock was limited to two things when it didn’t close for two hours."
Reviewed on Jul 18, 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.
Stay near popular Upper Matecumbe Key attractions
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- Princeton Hotels
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- Adults Only Resorts & in Marathon
- Palaces in Key Colony Beach
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- Scuba Diving Hotels in Blue Waters
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- All-Inclusive Hotel Hotels in Key Largo Park
- Scuba Diving Hotels in Key Largo Village
- Rv Parks in Islamorada
- Resorts in Duck Key
- Hotels near Homestead Miami Speedway
- Rv Parks in Bahia Honda Key
- Long Key Hotels
- Waterpark Hotels in Florida City
- Farmstay in Marathon
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- Vacation Homes in Marathon
- Resorts in Key Colony Beach
- Lodges in Homestead
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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.
