
Upper Matecumbe Key Vacation Packages
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Top Upper Matecumbe Key Vacation Deals
Price found within the past 48 hours. Click for updated prices.


Casablanca Miami Beach
North Beach
Price was CA $12,126, price is now CA $5,595 per person
CA $5,595
per person
Jul 26 - Aug 1
found 9 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
5.8/10 (324 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great.
It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.
Reviewed on Feb 22, 2026


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 CA $330 per night from Jul 19 to Jul 20
CA $330
CA $475 total
Jul 19 - Jul 20
includes taxes & fees
9.2/10 Wonderful! (1,329 reviews)
"The decor was updated a bit but then dated in other areas. The balcony cushions had stains and the carpet needed to be replaced."
Reviewed on Jun 23, 2026

Amara Cay Resort
80001 Overseas Hwy Islamorada FL
The price is CA $231 per night from Jul 8 to Jul 9
CA $231
CA $364 total
Jul 8 - Jul 9
includes taxes & fees
8.8/10 Excellent! (1,294 reviews)
"Enjoyed the food & pool."
Reviewed on Jun 24, 2026

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is CA $263 per night from Jul 2 to Jul 3
CA $263
CA $375 total
Jul 2 - Jul 3
includes taxes & fees
9.2/10 Wonderful! (1,743 reviews)
"Everything here was amazing! It was my first time in the keys and I’ll never forget it!"
Reviewed on Jun 23, 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.
Discover the most popular places to visit in Upper Matecumbe Key

History of Diving Museum
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
The memories of those lost to the 1935 Labor Day Hurricane live on at this moving tribute and burial site along the Overseas Highway.
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- Anhinga Trail
- Anne's Beach
- Baker's Cay Resort Beach
- Bluefin Rock Harbor Marina
- Coco Plum Beach
- Crane Point Museum and Nature Center
- Curry Hammock State Park
- Cutler Ridge Mall
- Dagny Johnson Key Largo Hammock Botanical State Park
- Duck Key Vacations
- Ernest F. Coe Visitor Center
- Everglades National Park
- Fiesta Key
- Florida City Vacations
- History of Diving Museum
- Homestead Miami Speedway
- Homestead Vacations
- Hurricane Monument
- Islamorada Vacations
- Visit Islamorada
- Key Largo Vacations
- Marathon Vacations
- Marinelab Undersea Laboratory
- Mayor Roscoe Warren Municipal Park
- North Key Largo Vacations
- Plantation Key Vacations
- Prime Outlets Florida City
- Seven Mile Bridge
- Sombrero Beach
- Sunset Park Beach
- Windley Key Fossil Reef Geological State Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.








