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



Cavalier Hotel South Beach
South Beach
Price was CA $1,571, price is now CA $797 per person
CA $797
per person
Nov 1 - Nov 8
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
Loved the Art Deco look of the rooms, lobby and hallway. Staff was very kind and helpful.
Reviewed on Aug. 16, 2025

Bentley Hotel South Beach
South Beach
Price was CA $2,311, price is now CA $1,207 per person
CA $1,207
per person
Nov 1 - Nov 8
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.2/10 Wonderful! (294 reviews)
The room was amazing with ocean view, the staff super friendly and the breakfast included really good, memorable experience.
Reviewed on Aug. 17, 2025

The Penguin Hotel
South Beach
Price was CA $1,554, price is now CA $813 per person
CA $813
per person
Nov 1 - Nov 8
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.2/10 Very Good! (1,414 reviews)
The only thing missing was breakfast. We were given drink vouchers, however we don’t drink.
Reviewed on Aug. 21, 2025
Lower Matecumbe Key Hotel Deals

Matecumbe Resort
76261 Overseas Hwy, Islamorada, FL
The price is CA $161 per night from Aug 24 to Aug 25
CA $161
CA $181 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (70 reviews)
"Rooms where clean, cool, and comfortable. I will visit again."
Reviewed on Aug. 20, 2025

Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 8.9.25
Islamorada
10/10 Exceptional! (46 reviews)
FABULOUS ACCOMODATIONS!
"Our family of eleven vacationed together to help celebrate our 50th wedding anniversary. The house was very well equipped with all of our needs.The upstairs toilets both had some issues with running until we jiggled the handles. Also the hand towel holder needs to be repaired, as it was broken upon ..."
Reviewed on Jul. 5, 2025

Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Sep 23 to Sep 24
CA $159
CA $257 total
Sep 23 - Sep 24
includes taxes & fees
9/10 Wonderful! (1,493 reviews)
"Morning breakfast was great. Staff was very attentive and pleasant. Room view was amazing. Very convenient for a person in our party that is disabled."
Reviewed on Aug. 21, 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 Lower Matecumbe Key

Anne's Beach
4/5(14 reviews)
If a restful vacation is part of your travel plans, Anne's Beach might be the perfect place to seek out during your trip to Islamorada.
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