Matecumbe Vacation Packages
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Top Holiday Package Deals in Matecumbe
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $17,948
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) 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
Viscay Hotel
South Beach
CA $1,795
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.2/10 Very good! (341 reviews)
Great location and great value. If you have an early flight before reception opens I’d suggest to arrange check out process beforehand
Reviewed on Jul 16, 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 Islamorada County Park 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
CA $205
CA $331 total
Aug 27 - Aug 28
includes taxes & fees
9.2/10 Wonderful! (1,425 reviews)
"Beautiful large room. Very luxurious. Grounds are perfect!"
Reviewed on Aug 24, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
CA $200
CA $302 total
Sep 20 - Sep 21
includes taxes & fees
9.2/10 Wonderful! (1,767 reviews)
"Great stay"
Reviewed on Aug 24, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
CA $213
CA $340 total
Aug 27 - Aug 28
includes taxes & fees
8.8/10 Excellent! (1,303 reviews)
"Room was clean. Pool and bar was great. The only complaint I have is the service at breakfast was extremely slow. Seemed they were understaffed."
Reviewed on Aug 24, 2026
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 family-friendly 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?
Lorelei Restaurant & Cabana Bar
After visiting Lorelei Restaurant & Cabana Bar, make a plan to see the other sights and activities in Islamorada.
Things to do
Tavernier, FL: Mangrove and Manatees Guided Kayak Eco Tour
CA $97
per adult
Islamorada Sunset Cruise with Champagne Toast and Snacks
CA $100
per adult
80% of travellers recommend
Snorkel and Sandbar Combo Adventure in Islamorada
CA $156
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.