Upper Matecumbe Key Trips (flight + hotel)

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    Save up to P 3,118 when you book a flight and hotel together*
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Top hotels in Upper Matecumbe Key

Chesapeake Beach Resort
Chesapeake Beach Resort
3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is P13,872 per night from Jul 23 to Jul 24
P13,872
P18,777 total
Jul 23 - Jul 24
includes taxes & fees
9/10 Wonderful! (1,484 reviews)
"Nice place to stay."

Reviewed on Jul 2, 2025

Chesapeake Beach Resort
Amara Cay Resort
Amara Cay Resort
4 out of 5
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is P10,106 per night from Jul 6 to Jul 7
P10,106
P15,112 total
Jul 6 - Jul 7
includes taxes & fees
8.8/10 Excellent! (1,221 reviews)
"Place was clean and the amenities are really nice. This is our third time in this hotel and we missed the store to buy essentials and souvenirs and we missed also the ice creams options, the ice cream fridge was empty."

Reviewed on Jun 30, 2025

Amara Cay Resort
Cheeca Lodge & Spa
Cheeca Lodge & Spa
5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is P9,521 per night from Jul 14 to Jul 15
P9,521
P14,514 total
Jul 14 - Jul 15
includes taxes & fees
9/10 Wonderful! (1,116 reviews)
Great Family weekend
"Great Resort. Family loved it ! Gary the server in Sushi restaurant was awesome."

Reviewed on Jun 29, 2025

Cheeca Lodge & Spa
See all 2,745 properties in Upper Matecumbe Key
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.

Popular places to visit

Islamorada Brewery & Distillery

You can take time to visit Islamorada Brewery & Distillery during your travels to Islamorada.

Islamorada Brewery & Distillery

MoradaWay Arts & Cultural District

You can spend time browsing the exhibits at MoradaWay Arts & Cultural District during your travels in Islamorada.

MoradaWay Arts & Cultural District

Keys History & Discovery Center

You can spend time exploring the galleries in Keys History & Discovery Center during your trip to Islamorada.

Keys History & Discovery Center

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.