
Matecumbe Vacation Packages
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Top Holiday Package Deals in Matecumbe
Price found within the past 48 hours. Click for updated prices.



Ridley House - Key West Historic Inns
Key West Historic District
Price was CA $3,366, price is now CA $1,680 per person
CA $1,680
per person
Oct 12 - Oct 19
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (815 reviews)
The staff were wonderful and we loved the breakfast and sangria hour and how walkable the area was! We walked everywhere during our stay. The only downsides were it is very noisy, since you can hear everything outside from in the room, and the AC in our room took about 2 days to cool down enough to be comfortable after the previous guests apparently had left the AC off and the windows open during their stay.
Reviewed on Sep. 3, 2025

Flow Miami Hotel
Downtown Miami
Price was CA $2,276, price is now CA $1,145 per person
CA $1,145
per person
Nov 16 - Nov 23
found 24 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Miami (MIA)
9/10 Wonderful! (154 reviews)
I really enjoyed my two night stay at Flow Miami Hotel. This place is really more of a hybrid of a hotel and a short term apartment rental and my accommodation was a well furnished one bedroom apartment. While the kitchen and extra space was nice the facilities (pool, gym) and service was the real stand-out for me. I look forward to returning! Please note a couple of cons though: 1) there is a lot of loud construction in the area and 2) they really don't offer much in the way of Expedia VIP offerings (free cafe beverage) so if these things bother you take that into account. Overall, I highly recommend this place.
Reviewed on Sep. 7, 2025

Ella's Cottages - Key West Historic Inns
Old Town Key West
Price was CA $4,285, price is now CA $2,273 per person
CA $2,273
per person
Nov 16 - Nov 22
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.4/10 Exceptional! (369 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
Where to stay in Matecumbe
Find the best Matecumbe areas and neighborhoods for the activities you enjoy most. Learn more about Matecumbe

Venetian Shores
Venetian Shores might not have many top sights, but Islamorada County Park and Founders Park are two attractions nearby that you can check out.
Matecumbe 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 9 to Sep 10
CA $169
CA $268 total
Sep 9 - Sep 10
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 $178 per night from Sep 9 to Sep 10
CA $178
CA $294 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 $219 per night from Sep 11 to Sep 12
CA $219
CA $339 total
Sep 11 - Sep 12
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 Matecumbe

Anne's Beach
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.

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.
Things to do

Golden Glare Fishing Charter with Experienced Captain
CA $893
per traveller

Ft Lauderdale to Islamorada Tour with Boat Ride and Lunch
CA $342
per adult
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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.