
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.

Pelican Grand Beach Resort - A Noble House Resort
East Fort Lauderdale
Price was CA $1,544, price is now CA $877 per person
CA $877
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.8/10 Excellent! (1,193 reviews)
I thoroughly enjoyed my seaside suite. Gorgeous view. Loved that the property is located on the beach. The outdoor beach service is immaculate. John provides wonderful service with a smile. Throughout the property, I found the staff to be kind and attentive. I also enjoyed the pool area and the rooftop spa- it’s small but the service was quality. All in all- I enjoyed my respite at The Pelican.
Reviewed on Aug. 24, 2025


Bentley Hotel South Beach
South Beach
Price was CA $2,379, price is now CA $1,247 per person
CA $1,247
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.2/10 Wonderful! (294 reviews)
friendly staff, complimentary chairs, early check in.
Reviewed on Aug. 27, 2025

EAST Miami Residences
Downtown Miami
Price was CA $3,479, price is now CA $1,977 per person
CA $1,977
per person
Nov 4 - Nov 9
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
9/10 Wonderful! (73 reviews)
This place is very beautiful, greats views with great customer service. This place just makes you feel very comfortable like your at home
Reviewed on Aug. 20, 2025

Carillon Miami Wellness Resort
North Beach
Price was CA $3,343, price is now CA $1,922 per person
CA $1,922
per person
Oct 19 - Oct 26
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.8/10 Excellent! (752 reviews)
The Hotel is really good, we went to the spa and got a massage and it was really good and relaxing. Definitely will go back
Reviewed on Aug. 13, 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 $169 per night from Sep 10 to Sep 11
CA $169
CA $268 total
Sep 10 - Sep 11
includes taxes & fees
9/10 Wonderful! (1,499 reviews)
"Fresh new rooms. Location was right on the ocean. Great breakfast, made for you. Front desk staff was amazing. Super accommodating and great communication. The only thing I would have recommended is that during construction they should have instated a bathroom vanity. Would return there again!!"
Reviewed on Aug. 24, 2025

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is CA $220 per night from Sep 4 to Sep 5
CA $220
CA $341 total
Sep 4 - Sep 5
includes taxes & fees

Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is CA $232 per night from Sep 10 to Sep 11
CA $232
CA $352 total
Sep 10 - Sep 11
includes taxes & fees
8.8/10 Excellent! (1,240 reviews)
"Beautiful and the smell is wonderful"
Reviewed on Aug. 25, 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.
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.
Frequently asked questions
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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.