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.
Park Central South Beach
South Beach
Price was CA $2,359, price is now CA $1,112 per person
CA $1,112
per person
Oct 15 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.2/10 Very Good! (946 reviews)
Perfect location, great restaurants and bars nearby, and good service!
Reviewed on Aug. 29, 2025
Pelican Grand Beach Resort - A Noble House Resort
East Fort Lauderdale
Price was CA $2,429, price is now CA $1,220 per person
CA $1,220
per person
Oct 15 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.8/10 Excellent! (1,211 reviews)
Room and property were good . Rocks in lazy river . Not enough tubes . Poor bar service. .
Very expensive for parking .
Could not understand girl at check in I have no idea what she was saying .
Door in room was hard to close , toilet paper dispenser was falling off wall . Mattress was mushy .views were outstanding . Location very good .
Reviewed on Aug. 29, 2025
Ella's Cottages - Key West Historic Inns
Old Town Key West
Price was CA $3,706, price is now CA $1,997 per person
CA $1,997
per person
Nov 10 - Nov 15
found 18 hours ago
Roundtrip flight included
Vancouver (YVR) to Key West (EYW)
9.4/10 Exceptional! (367 reviews)
This property is absolutely adorable! Room was clean and spacious. Front desk person was very nice and personable. The breakfast baskets that are delivered to your room are top notch! Will definitely be staying here again!
Reviewed on Aug. 31, 2025
EAST Miami
Downtown Miami
Price was CA $2,215, price is now CA $1,252 per person
CA $1,252
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.2/10 Wonderful! (3,330 reviews)
Very good ! The only thing I did not like is that for a 5 star hotel they do not have 24 hour room service
Reviewed on Aug. 30, 2025
Upper Matecumbe Key Hotel Deals
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Sep 1 to Sep 2
CA $168
CA $267 total
Sep 1 - Sep 2
includes taxes & fees
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is CA $218 per night from Sep 9 to Sep 10
CA $218
CA $339 total
Sep 9 - Sep 10
includes taxes & fees
Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is CA $231 per night from Sep 3 to Sep 4
CA $231
CA $351 total
Sep 3 - Sep 4
includes taxes & fees
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
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.
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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.