Upper Matecumbe Key Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Cameron Abbott

  • Plan, book, travel with confidence

  • Better together

    Save up to Rp16.000.000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Upper Matecumbe Key

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is Rp4.256.325 per night from 13 Jul to 14 Jul
Rp4.256.325
Rp6.089.641 total
13 Jul - 14 Jul
includes taxes & fees
9.2/10 Wonderful! (1,319 reviews)
"There was a lot of seaweed, which definitely had an odor; it was impossible to use the beach area. I did expect they would make more of an effort to clean it. Could use some TCL, adult pool needs new steps that do not get too hot to touch in the summertime. (They make them now). Could have made more ..."

Reviewed on 18 Jun 2026

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 Rp3.532.999 per night from 22 Jun to 23 Jun
Rp3.532.999
Rp4.975.536 total
22 Jun - 23 Jun
includes taxes & fees
9.2/10 Wonderful! (1,728 reviews)
"Great resort with friendly staff. Very clean!"

Reviewed on 19 Jun 2026

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 Rp5.124.672 per night from 28 Jun to 29 Jun
Rp5.124.672
Rp6.966.351 total
28 Jun - 29 Jun
includes taxes & fees
9.4/10 Exceptional! (1,054 reviews)
"The resort is absolutely beautiful! The room is immaculate , and you even have a walk out patio . Two pools, one for relaxation and the other for “kids” I am impressed at this resort."

Reviewed on 18 Jun 2026

Islander Resort
See all 2,778 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_MatecumbeUnitedMethodistChurch_553248621532652347-0004

Matecumbe United Methodist Church

After visiting Matecumbe United Methodist Church, make a plan to see the other sights and activities in Islamorada. Discover the beautiful sunsets in this family-friendly area or enjoy its fishing spots.

Matecumbe United Methodist Church
Hurricane Monument

Hurricane Monument

The memories of those lost to the 1935 Labor Day Hurricane live on at this moving tribute and burial site along the Overseas Highway.

Hurricane Monument

Frequently asked questions

Can I cancel my flight booking to Upper Matecumbe Key due to COVID-19?
Many airlines now provide more flexibility due to COVID-19. Our convenient Customer Service Portal will help solve most questions about which policies apply to your Upper Matecumbe Key flight. It's also worth scanning over the terms and conditions of your airfare — preferably before you make a booking!
What's the best way to find cheap flights to Upper Matecumbe Key that have flexible change policies?
At Expedia, we've been channeling our inner yogi to help you locate the most flexible fares around town. Just check the "No change fee" box right underneath the filter subheading "Flexible change policies" to find your perfect flight to Upper Matecumbe Key.
What are some of the general tips for travellers to Upper Matecumbe Key during the COVID-19 outbreak?
COVID-19 has brought about significant changes to how we travel. If you're planning a holiday in Upper Matecumbe Key, these tips will help you navigate travel's newest challenges:
  • Look into if any restrictions apply to both your origin and destination. You may not be able to travel depending on local circumstances, so be sure to check before you book.
  • When you go through airport checkpoints, do not remove your face mask. You will be asked to lower it briefly to confirm your identity. Those who refuse to wear a face mask may face civil penalties and may also be escorted from the terminal.
  • Instead of handing a TSA officer your boarding pass, position it straight on the scanner yourself. When that's done, hold it up for inspection.
  • One liquid hand sanitizer container is now permitted in your carry-on luggage. It must be no larger than 12 oz (350 ml), and you'll have to remove it from your bag for X-ray screening.
  • Put any personal items (phone, wallet and keys for example) in your carry-on rather than a bin to minimize handling during screening.
  • Transport any food items in a clear plastic bag and also place them in a screening bin. Keeping your food separate from your carry-on makes it less likely that a TSA officer will need to open and touch your bag for inspection.

Which airlines fly to Upper Matecumbe Key?
Delta is a widely known airline servicing Upper Matecumbe Key. Book a ticket to Key West Intl. Airport (EYW) and you'll have 191 Delta flights per month to select from.
How can I find cheap tickets to Upper Matecumbe Key?
You'll always pick up a terrific deal with Expedia, but our "flexible dates" search function makes it that much easier. Enter your preferred travel date, then tick the flexible dates box above to see prices for nearby days. was the lowest price for a flight to Upper Matecumbe Key in the last seven days.
How much is a flight to Upper Matecumbe Key?
The price of a round-trip ticket to Upper Matecumbe Key in the last seven days ranged between and . If you were heading one way from (), you could have nabbed an affordable fare from just .
What are the most popular airports to fly into in Upper Matecumbe Key?
Key West Intl. Airport (EYW) is the main point of entry for those hoping to visit Upper Matecumbe Key. Around 1119 flights per month touch down here.
When is the cheapest time to fly to Upper Matecumbe Key?
If you'd rather spend your cash exploring Upper Matecumbe Key rather than on getting there, take off early in the week. The most economical day to fly is usually Tuesday, with Monday a close second. With many folks keeping their travel to weekends, Saturday often has the most expensive airfares.
How much is a plane ticket to Upper Matecumbe Key?
Airfares ranged from to in the last seven days. When you're ready to book, we'll be ready to help you secure the best price to Upper Matecumbe Key.
What months are the cheapest to book a flight to Upper Matecumbe Key?
Score a ticket in February to unlock awesome flight deals to Upper Matecumbe Key. The month of December is known to be the most expensive time to buy an airfare.
Which airlines with flights to Upper Matecumbe Key employ COVID-19 cleanliness policies?
In response to the global COVID-19 pandemic, the majority of airlines have introduced new precautionary measures to help their passengers and staff get back in the air. Here are some good examples:
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

How long is a flight to Upper Matecumbe Key?
It could be a couple of hours or more — it mainly depends on which part of the U.S. You're travelling from. The average flight times for these busy domestic routes to Upper Matecumbe Key will give you a clearer picture of what to expect:
  • Atlanta, GA Airport (ATL-Hartsfield-Jackson Atlanta Intl.) to Key West Intl. Airport (EYW) - 1 hour and 50 minutes
  • Charlotte, NC Airport (CLT-Charlotte-Douglas Intl.) to Key West Intl. Airport (EYW) - 2 hours and 8 minutes
  • Miami, FL Airport (MIA-Miami Intl.) to Key West Intl. Airport (EYW) - 55 minutes

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.