
Lower Matecumbe Key Vacations from $196
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The Latest Lower Matecumbe Key vacation packages
Price found within the past 48 hours. Click for updated prices.

Hollywood Gateway Inn
North Central Hollywood
Price was $439, price is now $196 per person
$196
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
6.6/10 (1,005 reviews)
I would say room is okay it was recently renovated wasn't thrilled about the lack of proper patio doors that wouldn't even close because they're so old therefore noisier than it should have been from the parking lot and in the morning the office is locked even though there's people inside and you can't get to the breakfast starting at 7:00 am. Is way too late
Reviewed on Nov 5, 2025

The Shelborne By Proper, a Member of Design Hotels
South Beach
Price was $1,546, price is now $645 per person
$645
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.8/10 Exceptional! (39 reviews)
Fantastic experience. One of the best hotels we have stayed at. Shout out to Jenny, Marta , Shane and Louis, William and Josh and all of the other wonderful staff. Definitely recommend it and will certainly go back !
Reviewed on Nov 1, 2025



Bentley Hotel South Beach
South Beach
Price was $3,216, price is now $1,546 per person
$1,546
per person
Dec 21 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (390 reviews)
Beautifully renovated with great additional touches like Continental breakfast and champagne at 5:00
Reviewed on Nov 7, 2025
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See all available trips from Columbus to Lower Matecumbe Key
View all tripsDiscover the most popular places to visit in Lower Matecumbe Key

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.
Sunset Drive Beach
Why not spend a lazy afternoon at Sunset Drive Beach during your trip to Islamorada?
Lower Matecumbe Key Hotel Deals

Matecumbe Resort
76261 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $141 total per night from Nov 10 to Nov 11
$141 total
Nov 10 - Nov 11
Total with taxes and fees
8.8/10 Excellent! (81 reviews)
Quiet, simple and clean. Office staff is not available before 9:30am or after 4pm. Parking is supposed to be 1 per unit. However, lack of office staff meant that when people had multiple cars or friends over, there was no parking. Could not complain to anyone.
Reviewed on Oct 20, 2025

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
$249 nightly
The price is $281 total per night from Nov 20 to Nov 21
$281 total
Nov 20 - Nov 21
Total with taxes and fees
9/10 Wonderful! (1,250 reviews)
Clean room and well-appointed amenities. Housekeeping did a commendable job. Patrick, the bartender at the tiki bar near outside dining was GREAT !
Reviewed on Nov 6, 2025

Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$181 nightly
The price is $204 total per night from Nov 16 to Nov 17
$204 total
Nov 16 - Nov 17
Total with taxes and fees
9.2/10 Wonderful! (1,552 reviews)
Friendly staff
Reviewed on Nov 2, 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.
Find the Best Lower Matecumbe Key Vacation Packages
Lower Matecumbe Key Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Key West Intl. Airport (EYW) |
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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.



















