Matecumbe Vacations from $445
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to $1,045 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
The Latest Matecumbe Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Creekside Inn Islamorada
Save 100% on your flight
Price was $841, price is now $445 per person
$445
per person
Nov 9 - Nov 15
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,006 reviews)
We like the place, but were disappointed Mar Bar was closed. Not a big deal, but the construction along the waterfront wasn’t pretty.
Reviewed on Sep 28, 2025
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,315, price is now $678 per person
$678
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,005 reviews)
Everyone and everything was great, such a great location to enjoy the whole island!
Reviewed on Sep 28, 2025
Pelican Grand Beach Resort - A Noble House Resort
East Fort Lauderdale
Save 100% on your flight
Price was $1,673, price is now $862 per person
$862
per person
Dec 1 - Dec 7
found 2 days ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.8/10 Excellent! (1,238 reviews)
The hotel needs significant maintenance
Reviewed on Sep 26, 2025
Ridley House - Key West Historic Inns
Key West Historic District
Save 100% on your flight
Price was $1,428, price is now $770 per person
$770
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (819 reviews)
Everything was amazing.
we arrived early and in a rain storm my two kids and I were soaked head to toe and the water even entered our luggage. they let us check in early got us en upgrade to.
amazing staff and perfect spot close to all in Key West
Reviewed on Sep 25, 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
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $172 total per night from Oct 1 to Oct 2
$172 total
Oct 1 - Oct 2
Total with taxes and fees
9/10 Wonderful! (1,216 reviews)
"Great resort for vacation.I liked everything about This place except for parking lots for beach bungalows rooms"
Reviewed on Sep 28, 2025
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $179 total per night from Sep 30 to Oct 1
$179 total
Sep 30 - Oct 1
Total with taxes and fees
9/10 Wonderful! (1,534 reviews)
"Everything was perfect and beautiful"
Reviewed on Sep 23, 2025
Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$227 nightly
The price is $256 total per night from Oct 2 to Oct 3
$256 total
Oct 2 - Oct 3
Total with taxes and fees
8.8/10 Excellent! (1,258 reviews)
"The resort had free kayaking and paddle boarding which was a great addition."
Reviewed on Sep 22, 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 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.
Florida Keys Brewing Co.
You can take time to visit Florida Keys Brewing Co. during your travels 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.
Things to do
Golden Glare Fishing Charter with Experienced Captain
$650
per traveler
Explore Mangrove Creeks with an All Day SUP/single kayak Rental
$47
per adult
Ft. Lauderdale to Key West Day Trip Quality Day Tours
$225
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.