Upper Matecumbe Key Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Upper Matecumbe Key

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 6.770.260 ₫ per night from 13 Aug to 14 Aug
6.770.260 ₫
9.381.123 ₫ total
13 Aug - 14 Aug
includes taxes & fees
9/10 Wonderful! (1,143 reviews)
"The bathroom got stuck, the shower was leaking."

Reviewed on 27 Jul 2025

Cheeca Lodge & Spa
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 3.957.510 ₫ per night from 12 Aug to 13 Aug
3.957.510 ₫
5.925.916 ₫ total
12 Aug - 13 Aug
includes taxes & fees
9/10 Wonderful! (1,496 reviews)
"Ac. Was not great at all. Wish there was more of a variety for food at bar area. We were starving had to order pizza. That was one reason for picking this resort. The breakfast was wonderful tho"

Reviewed on 28 Jul 2025

Chesapeake Beach Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is 5.437.120 ₫ per night from 11 Aug to 12 Aug
5.437.120 ₫
7.881.210 ₫ total
11 Aug - 12 Aug
includes taxes & fees
9/10 Wonderful! (1,021 reviews)
"Amazing. Truly nothing else compares. Staff is incredible."

Reviewed on 26 Jul 2025

Islander Resort
See all 2,807 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

Florida Keys Brewing Co.

Florida Keys Brewing Co.

You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.

Florida Keys Brewing Co.
History of Diving Museum

History of Diving Museum

You can spend an afternoon browsing the exhibits at History of Diving Museum during your travels in Islamorada. Amble around this family-friendly area's seaside and enjoy its lively bars.

History of Diving Museum
Hurricane Monument which includes outdoor art and a monument

Hurricane Monument

Learn about the local history of Islamorada when you take a trip to Hurricane Monument. Discover the beautiful sunsets and lively bars in this family-friendly area.

Hurricane Monument

Frequently asked questions

How much does an Upper Matecumbe Key holiday 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 holiday package. Sometimes cheap packages mean fewer choices. But that's not the case with Expedia. We offer more than 550 partner airlines and 1null000null000 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 holiday?
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 holiday package?
Yes — that's one of the best things about an Expedia holiday 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 holiday 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 holiday 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.