Upper Matecumbe Key Vacations from $449
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The Latest Upper Matecumbe Key vacation packages
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
$12,309
per person
Oct 24 - Oct 31
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
Luxuri Suites
South Beach
$496
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
6.8/10 (57 reviews)
Ok the fact we had no desk for check was terrible. I could not check in due to a code for door and room acess never being sent to my email resulted in me not checking for 3hours until I was told about a sister property 3 blocks from where I was stay had to walk in the rain to the siater property for thwm to grant me acess codes to get into my room now at 3am. I wouls likw to be reemburst for that night and day. My TV had no working batteries and once I go batteries the TV volum did not work.
Reviewed on Jul 9, 2026
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View all tripsStay near popular Upper Matecumbe Key attractions
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.
Islamorada Brewery & Distillery
9.4/10 (8 reviews)
You can take time to visit Islamorada Brewery & Distillery during your travels to Islamorada.
MoradaWay Arts & Cultural District
Enjoy an outing to MoradaWay Arts & Cultural District during your stay in Islamorada.
beach near Islamorada
Why not spend a lazy afternoon at beach near Islamorada during your trip to Islamorada?
Keys History & Discovery Center
You can spend time exploring the galleries in Keys History & Discovery Center 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.
Upper Matecumbe Key Hotel Deals
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$210 nightly
$236 total
Aug 27 - Aug 28
Total with taxes and fees
9.2/10 Wonderful! (1,420 reviews)
"We had a wonderful adults getaway! I do feel like it’s a bit dated but we would definitely return!! The seaweed was pretty bad."
Reviewed on Aug 23, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$195 nightly
$219 total
Aug 26 - Aug 27
Total with taxes and fees
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$224 nightly
$252 total
Aug 26 - Aug 27
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.
Find the Best Upper Matecumbe Key Vacation Packages
Upper Matecumbe Key Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Key West Intl. Airport (EYW) |
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- Sunset Drive Beach
- Baker's Cay Resort Beach
- Pigeon Key
- Pinecrest Vacations
- Windley Key Fossil Reef Geological State Park
- Visit Key Largo
- Jimmy Johnson's Big Chill
- Anne's Beach
- Everglades National Park
- Fiesta Key
- Conch Key Vacations
- Jacob's Aquatic Center
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- Florida Keys Dive Center
- Sombrero Beach
- History of Diving Museum
- Matecumbe United Methodist Church
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- Hurricane Monument
- Visit Upper Matecumbe Key
- Long Key Vacations
- Tavernier Vacations
- Long Key State Park
- Florida Keys Brewing Co.
- Marinelab Undersea Laboratory
- Key Largo Vacations
- Visit Islamorada
- Bluefin Rock Harbor Marina
- Islamorada Vacations
- Bud n' Mary's Dive Center
- Islamorada County Park
- Marathon Vacations
- Harry Harris Park
- Coral Castle Museum
- All inclusive Vacation Packages Key Largo
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
