Upper Matecumbe Key Vacations
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Find the Best Upper Matecumbe Key Vacation Packages
Upper Matecumbe Key Hotel Deals
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
₩265,625
₩396,443 total
Nov 3 - Nov 4
includes taxes & fees
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
₩201,621
₩301,907 total
Nov 3 - Nov 4
includes taxes & fees
9.2/10 Wonderful! (1,800 reviews)
"Lovely place to stay in Islamorada. Beach and pools were great. Fantastic breakfast included with made to order omelettes. Parking was available. We stayed in the most basic room which was in the building by the office so we could hear traffic from the Overseas Highway but was it pretty quiet inside ..."
Reviewed on Oct 12, 2026
Islander Resort
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
₩293,785
₩428,508 total
Oct 14 - Oct 15
includes taxes & fees
9.4/10 Exceptional! (1,139 reviews)
"Fabulous bedroom cozy bed and awesome hot shower. Couch was sorta cheap and no fridge but we loved the ice maker and kitchenette. We loved the pool and the staff. Weak drinks but good food. The feeling there is soooo great. Will 100% come back."
Reviewed on Oct 13, 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 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 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.
Hurricane Monument
8.6/10 (250 reviews)
The memories of those lost to the 1935 Labor Day Hurricane live on at this moving tribute and burial site along the Overseas Highway.
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.
Lorelei Restaurant & Cabana Bar
After visiting Lorelei Restaurant & Cabana Bar, make a plan to see the other sights and activities in Islamorada.
beach near Islamorada
Why not spend a lazy afternoon at beach near Islamorada during your trip to Islamorada?
Frequently asked questions
How much does an Upper Matecumbe Key vacation package cost?
Starting from a low , a package is your passport to low-cost travel. Custom make your Upper Matecumbe Key getaway by selecting from our huge range of hotels, airfares and rental cars.
How do I get a cheap travel package to Upper Matecumbe Key?
You'll save loads of cash if you combine your hotels, flights and car rentals into an Upper Matecumbe Key vacation package. Sometimes cheap packages mean fewer choices. But that's not the case with Expedia. We offer more than 550 partner airlines and 1,000,000 properties throughout the world, so you'll always have plenty of variety to choose from. Eager to save even more? Add some exciting activities to your package deal to unlock even more discounts! After all, travel is about more than simply getting to your destination.
How far in advance should I book my Upper Matecumbe Key vacation?
While prices change frequently, we generally suggest booking your spot as soon as possible. Many international airfares are available on Expedia up to a year in advance. If you're booking late, you may still get lucky. Cheap tickets to Upper Matecumbe Key sometimes appear just weeks before departure.
What does an Expedia Upper Matecumbe Key travel package include?
Flights, car rentals and hotels — we connect you to the very best bargains. All you'll have to do is figure out your preferred combination. After you've made your booking, you can add on the fun stuff like sightseeing activities. Our travel packages make it easy to put together an exciting Upper Matecumbe Key escape.
What should I know before booking an Upper Matecumbe Key travel package?
We already have low prices. However, you'll enjoy an even better deal if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and loads of choice.
Can I choose my airline with an Upper Matecumbe Key Expedia vacation package?
Yes — that's one of the best things about an Expedia vacation package. You're in control. We have access to more than 550 airline partners worldwide, so you have lots of choice when putting together your Upper Matecumbe Key adventure.
If I'm not able to travel, can I cancel my Upper Matecumbe Key vacation package?
You sure can, and we'll help you every step of the way. You may be able to amend or cancel your Upper Matecumbe Key vacation package for free within 24 hours of booking. However, you may be charged a fee by your hotel, airline or car rental company for older bookings. If your travel plans unexpectedly change, look up our Customer Service Portal for more information.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
