
Upper Matecumbe Key Trips (flight + hotel)
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Top hotels in Upper Matecumbe Key

Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is P13,842 per night from Jul 23 to Jul 24
P13,842
P18,736 total
Jul 23 - Jul 24
includes taxes & fees
9/10 Wonderful! (1,484 reviews)
"Nice place to stay."
Reviewed on Jul 2, 2025

Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is P12,193 per night from Jul 7 to Jul 8
P12,193
P17,452 total
Jul 7 - Jul 8
includes taxes & fees
8.8/10 Excellent! (1,219 reviews)
"Place was clean and the amenities are really nice. This is our third time in this hotel and we missed the store to buy essentials and souvenirs and we missed also the ice creams options, the ice cream fridge was empty."
Reviewed on Jun 30, 2025

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is P9,507 per night from Jul 7 to Jul 8
P9,507
P14,493 total
Jul 7 - Jul 8
includes taxes & fees
9/10 Wonderful! (1,116 reviews)
Great Family weekend
"Great Resort. Family loved it ! Gary the server in Sushi restaurant was awesome."
Reviewed on Jun 29, 2025
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.
Popular places to visit
Islamorada Brewery & Distillery
You can take time to visit Islamorada Brewery & Distillery during your travels to Islamorada.
MoradaWay Arts & Cultural District
You can spend time browsing the exhibits at MoradaWay Arts & Cultural District during your travels in Islamorada.
Keys History & Discovery Center
You can spend time exploring the galleries in Keys History & Discovery Center during your trip to Islamorada.
Frequently asked questions
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Packages
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.