Matecumbe Vacations from $376
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The Latest Matecumbe Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
$16,302
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
Avi Lux Stay
East Fort Lauderdale
$791
per person
Jan 11 - Jan 16
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
7.6/10 Good! (10 reviews)
If you are looking for a quiet place to stay this suite is NOT recommended. You can hear motorcycles and racing cars at all hours of the night. Valet is $60 per night mandatory payment required upon check in for the entire length of your stay tips not included. This is not stated in the description prior to booking. BEWARE.
Reviewed on Aug 28, 2025
The Penguin Hotel
South Beach
$1,241
per person
Dec 29 - Jan 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,996 reviews)
Everything was excellent at the property except for the ac in our room automatically comes on and off even though the room was hot
Reviewed on Oct 17, 2026
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 Rain Barrel Village and Founders Park are two attractions nearby that you can check out.
Lower Matecumbe Beach
Though Lower Matecumbe Beach might not have many top sights, you can venture to the surrounding area to see attractions like Anne's Beach and Sunset Drive Beach.
Seabreeze Trailer Park
If you're looking for some top things to see and do in Seabreeze Trailer Park and surrounding area, you can visit Founders Park and Islamorada County Park.
Matecumbe Hotel Deals
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$232 nightly
$261 total
Oct 19 - Oct 20
Total with taxes and fees
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$172 nightly
$194 total
Nov 4 - Nov 5
Total with taxes and fees
9.4/10 Exceptional! (1,798 reviews)
"Super el hotel"
Reviewed on Oct 17, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$208 nightly
$234 total
Oct 21 - Oct 22
Total with taxes and 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.
Stay near popular Matecumbe attractions
Anne's Beach
7.8/10 (597 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.
Bud n' Mary's Dive Center
8.8/10 (504 reviews)
Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this relaxing area.
Florida Keys Brewing Co.
9.2/10 (520 reviews)
You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.
History of Diving Museum
9.0/10 (177 reviews)
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.
Robbie’s of Islamorada
8.4/10 (15 reviews)
Explore the waterfront in Islamorada with a trip to Robbie’s of Islamorada.
Islamorada Brewery & Distillery
9.4/10 (8 reviews)
You can take time to visit Islamorada Brewery & Distillery during your travels to Islamorada.
Sunset Drive Beach
9.0/10 (91 reviews)
Why not spend a lazy afternoon at Sunset Drive Beach during your trip to Islamorada?
beach near Islamorada
Why not spend a lazy afternoon at beach near Islamorada during your trip to Islamorada?
Things to do
Tavernier, FL: Mangrove and Manatees Guided Kayak Eco Tour
$69
per adult
100% of travellers recommend
Snorkel and Sandbar Combo Adventure in Islamorada
$111
per adult
Kayak through Mangrove Forests in the Florida Keys
$65
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.