Upper Matecumbe Key Vacations from $342

Book a Hotel + Flight or Car together to unlock savings

Photo by Cameron Abbott
  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Upper Matecumbe Key vacation packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Miami Airport-East
Cavalier Hotel South Beach
Creekside Inn
The Retreat Collection at 1 Hotel & Homes South Beach
Solé Miami, A Noble House Resort
Don't see what you're looking for?
See all available trips from Columbus to Upper Matecumbe Key
View all trips

Discover the most popular places to visit in Upper Matecumbe Key

Upper Matecumbe Key Hotel Deals

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$242 nightly
The price is $273 total per night from Feb 3 to Feb 4
$273 total
Feb 3 - Feb 4
Total with taxes and fees
9.2/10 Wonderful! (1,658 reviews)
Spacious clean room. Good linens and towels with comfortable beds. Staff very helpful. Elevator was broken but staff carried bags up,

Reviewed on Feb 1, 2026

Chesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$346 nightly
The price is $390 total per night from Feb 3 to Feb 4
$390 total
Feb 3 - Feb 4
Total with taxes and fees
9.2/10 Wonderful! (1,289 reviews)
Great staff and beautiful property

Reviewed on Jan 29, 2026

Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$306 nightly
The price is $345 total per night from Feb 9 to Feb 10
$345 total
Feb 9 - Feb 10
Total with taxes and fees
8.8/10 Excellent! (1,259 reviews)
We enjoyed our stay and found the staff to be courteous and responsive. Our room was a generous size, clean and well appointed (as is often the case we wouldn’t have said no to a couple of more outlets lol). The beach and pool areas had plenty of seating and multiple things to do—ping pong, cornhole, ...

Reviewed on Jan 26, 2026

Amara Cay Resort
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.

Find the Best Upper Matecumbe Key Vacation Packages

Upper Matecumbe Key Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)

More vacations you might like

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.