- Plan, book, travel with confidence
Better together
Save up to CA $1,096 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
Top Upper Matecumbe Key Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach
South Beach
Save 100% on your flight
per person
Feb. 16 - Feb. 23
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.4/10 Very Good! (1,006 reviews)
The thermostat didn’t work so I couldn’t put the heat on when it got cold at night and the elevator didn’t work properly
Reviewed on Jan. 5, 2025
1 Hotel South Beach
South Beach
Save 100% on your flight
per person
Feb. 16 - Feb. 23
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9.2/10 Wonderful! (1,043 reviews)
Best hotel I’ve ever stayed in - hands down! It was the most amazing experience. Love this hotel!
Reviewed on Jan. 6, 2025
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
The price is CA $432 per night from Jan. 8 to Jan. 9
CA $432
CA $583 total
includes taxes & fees
Jan 8 - Jan 9
9/10 Wonderful! (1,011 reviews)
"Beautiful property!"
Reviewed on Jan. 3, 2025
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is CA $230 per night from Jan. 7 to Jan. 8
CA $230
CA $331 total
includes taxes & fees
Jan 7 - Jan 8
9/10 Wonderful! (1,386 reviews)
"Really lovely property, nice updated room. Bathroom could use improved lighting for mirrors, but overall very nice! Front desk staff seemed a bit frazzled & slightly unprofessional, but some customer service training could easily improve that. The bar/breakfast service and staff were very good! Cleaning ..."
Reviewed on Jan. 3, 2025
Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is CA $337 per night from Jan. 8 to Jan. 9
CA $337
CA $476 total
includes taxes & fees
Jan 8 - Jan 9
8.8/10 Excellent! (1,213 reviews)
"Great stay"
Reviewed on Dec. 30, 2024
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.
Frequently asked questions
Discover the most popular places to visit in Upper Matecumbe Key
History of Diving Museum
4/5(1 review)
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(1 review)
The memories of those lost to the 1935 Labor Day Hurricane live on at this moving tribute and burial site along the Overseas Highway.
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
Hotels
Condo Rentals Turks and CaicosBeach Hotel in NicaraguaLa Fontanina SuitesAdmiral Inn HamiltonAdults Only Resorts & Hotels in Greece5 Star Hotels in BarcelonaBest Hotels in NanaimoNatura Cabana Boutique Hotel & Spa by MintBest Hotels in DarnleyBest Hotels in Hamilton GO CentreFour Points by Sheraton Midtown-Times SquareVictoria Inn Hotel and Convention Centre WinnipegMichigan International Speedway hotelsAparthotels VancouverHotel Du Vieux Quebec
Flights
Packages
Vacation Rentals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.