Upper Matecumbe Key Vacations

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Find the Best Upper Matecumbe Key Vacation Packages

Upper Matecumbe Key Hotel Deals

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 ₩209,790 per night from Aug 18 to Aug 19
₩209,790
₩314,139 total
Aug 18 - Aug 19
includes taxes & fees
9/10 Wonderful! (1,495 reviews)
"Overall it was a great resort that offered activities and a free continental breakfast. Omelette station was a pleasant surprise."

Reviewed on Aug 15, 2025

Chesapeake Beach 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 ₩220,832 per night from Aug 21 to Aug 22
₩220,832
₩342,185 total
Aug 21 - Aug 22
includes taxes & fees
9/10 Wonderful! (1,143 reviews)
"I booked last minute and what a fabulous surprise! The staff was amazing from check in with Anna, to Jordan at one of the outdoor Tiki bars and to G at the delish Sushi restaurant on site. The room was phenomenal and I loved the screened in patio. Great job! I will return."

Reviewed on Aug 15, 2025

Cheeca Lodge & Spa
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 ₩233,436 per night from Sep 1 to Sep 2
₩233,436
₩354,808 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,231 reviews)
"Top notch all around."

Reviewed on Aug 13, 2025

Amara Cay Resort
See all 2,766 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.

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.