
Upper Matecumbe Key Vacations from $506
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The Latest Upper Matecumbe Key vacation packages
Price found within the past 48 hours. Click for updated prices.

Beach Place Hotel
North Beach
Price was $1,051, price is now $506 per person
$506
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,007 reviews)
THe parking was very convenient,and well lit. There were shops close enough to walk but not so close that there were too many people. The best things is the proximity to the beach/park!
Reviewed on Oct 24, 2025

The Shelborne By Proper, a Member of Design Hotels
South Beach
Price was $2,290, price is now $933 per person
$933
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.8/10 Exceptional! (39 reviews)
Fantastic experience. One of the best hotels we have stayed at. Shout out to Jenny, Marta , Shane and Louis, William and Josh and all of the other wonderful staff. Definitely recommend it and will certainly go back !
Reviewed on Nov 1, 2025


Bentley Hotel South Beach
South Beach
Price was $1,997, price is now $949 per person
$949
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (390 reviews)
The staff was amazing and really helpful. Vanina helped us book a trip and Raenaldo was always most helpful, alingt with all the members of staff on duty for the week we stayed
Reviewed on Nov 2, 2025

President Hotel
South Beach
Price was $1,804, price is now $863 per person
$863
per person
Dec 3 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,905 reviews)
The staff is very helpful with information specially Henry and the lady who works at the same desk when he is off duty. Even the guy who is parking cars offered a usufull information about the area.
Reviewed on Oct 29, 2025
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See all available trips from Columbus to Upper Matecumbe Key
View all tripsDiscover the most popular places to visit in Upper Matecumbe Key

Florida Keys Brewing Co.
You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.

History of Diving Museum
4.5/5(51 reviews)
Trace one of the world’s most astonishing watersports back through the centuries to see some of the first diving suits as you explore this interactive museum, featuring the world's largest international collection of diving artifacts.

Hurricane Monument
4/5(66 reviews)
The memories of those lost to the 1935 Labor Day Hurricane live on at this moving tribute and burial site along the Overseas Highway.
Upper Matecumbe Key Hotel Deals

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
$259 nightly
The price is $291 total per night from Nov 3 to Nov 4
$291 total
Nov 3 - Nov 4
Total with taxes and fees
9/10 Wonderful! (1,265 reviews)
Always a great stay at Cheeca. Lovely property, great restaurants, clean rooms and wonderful service by the staff.
Reviewed on Oct 30, 2025

Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $186 total per night from Nov 5 to Nov 6
$186 total
Nov 5 - Nov 6
Total with taxes and fees
9.2/10 Wonderful! (1,548 reviews)
I was very pleased with the resort. It’s a quiet hidden gem with a friendly and helpful staff. I would love to stay here again.
Reviewed on Oct 27, 2025

Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$205 nightly
The price is $231 total per night from Nov 30 to Dec 1
$231 total
Nov 30 - Dec 1
Total with taxes and fees
8.8/10 Excellent! (1,270 reviews)
We enjoyed our stay a beautiful place, but there was no free breakfast
Reviewed on Oct 24, 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.
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) |
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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.



















