Matecumbe Vacations from $252
Book a Hotel + Flight or Car together to unlock savings
The Latest Matecumbe Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hawks Cay Resort
Price was $1,997, price is now $758 per person
$758
per person
Jan 19 - Jan 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,011 reviews)
Room was clean and spacious. Property did not have available microwave for guest. House keeping was good but did not replace soap or drinking glass. Gym not located in main hotel area and it closes at 5pm. Overall property is beautiful and good amenities.
Reviewed on Nov 7, 2025
The Shelborne By Proper, a Member of Design Hotels
South Beach
Price was $2,147, price is now $858 per person
$858
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.8/10 Exceptional! (39 reviews)
Lovely property. Staff service inconsistent overall. Room was not serviced one day. On the day there was construction above pool area, no notice was sent out. Pool area staff/manager and construction crew didn't seem to be on the same page.
Reviewed on Nov 13, 2025
Cavalier Hotel South Beach
South Beach
Price was $1,014, price is now $469 per person
$469
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,004 reviews)
Room was clean. Staff was friendly beach, restaurants and shops nearby. Also a convenient parking garage within walking distance.
Reviewed on Nov 4, 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
$245 nightly
The price is $276 total per night from Nov 19 to Nov 20
$276 total
Nov 19 - Nov 20
Total with taxes and fees
9/10 Wonderful! (1,259 reviews)
Beautiful grounds, immaculate rooms, divine sushi and meals! The pier is nonstop entertainment for kids, especially if they fish. There are activities for everyone in your family. Highly recommend this resort!
Reviewed on Nov 13, 2025
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $208 total per night from Nov 16 to Nov 17
$208 total
Nov 16 - Nov 17
Total with taxes and fees
9.2/10 Wonderful! (1,564 reviews)
Nice place, good location, friendly staff, clean room, good food, beat views, easy access to pool and beach.
Reviewed on Nov 9, 2025
Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$207 nightly
The price is $233 total per night from Nov 30 to Dec 1
$233 total
Nov 30 - Dec 1
Total with taxes and fees
8.8/10 Excellent! (1,245 reviews)
The rooms were clean, staff was friendly and helpful, food was delicious, the property was beautiful and loved how there was connections to the other resorts through van transportation or the Rum runner boat! Would definitely stay again!
Reviewed on Nov 8, 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
3.5/5(139 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.
Florida Keys Brewing Co.
You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.
History of Diving Museum
4.5/5(51 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.
Things to do
Explore Mangrove Creeks with an All Day SUP/single kayak Rental
$47
per adult
Explore the Mangrove Creeks with an ALL Day Tandem Kayak Rental
$65
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.