Lower Matecumbe Key Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 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 Lower Matecumbe Key

Matecumbe Resort

Matecumbe Resort

2 out of 5
76261 Overseas Hwy Islamorada FL
8.8/10 Excellent! (100 reviews)
Nice quiet location. Free kayak,bike rental was good. If you walk through rocky place you can fish everywhere and easy to catch. Shower was kinda broken but usable.

Reviewed on 9 Mar, 2026

Get rates
Matecumbe Resort
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 S$520 per night from 12 Apr to 13 Apr
S$520
12 Apr - 13 Apr
includes taxes & fees
9.2/10 Wonderful! (1,298 reviews)
We did not use the spa services, we may have been able to barely see a small portion of the ocean out a window

Reviewed on 12 Mar, 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 S$385 per night from 14 Apr to 15 Apr
S$385
14 Apr - 15 Apr
includes taxes & fees
9.2/10 Wonderful! (1,668 reviews)
Staff wasn’t very helpful or accommodating.

Reviewed on 15 Mar, 2026

Chesapeake Beach Resort
See all 2,135 properties in Lower 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

Sunset Drive Beach

Why not spend a lazy afternoon at Sunset Drive Beach during your trip to Islamorada?

Sunset Drive Beach

Frequently asked questions

Can I cancel my flight booking to Lower Matecumbe Key due to COVID-19?
Our Customer Service Portal is where you can find useful information about cancelling your Lower Matecumbe Key flight due to COVID-19. Before booking your tickets, it's a good idea to scroll through the terms and conditions of your preferred airline too.
What's the best way to find cheap flights to Lower Matecumbe Key that have flexible change policies?
At Expedia, we've been channeling our inner acrobat to give you the most flexible airfares around town. Simply check the "No change fee" box right underneath the filter heading "Flexible change policies" to find your perfect flight to Lower Matecumbe Key.
What are some of the general tips for travellers to Lower Matecumbe Key during the COVID-19 outbreak?
COVID-19 has led to big changes to the way we travel. If you're planning a trip to Lower Matecumbe Key, the following tips will help you navigate these new travelling challenges:
  • Before you lock in a flight, check if any travel restrictions or bans apply — in both your destination and origin. Get up-to-date information by checking government travel advisories.
  • Keep your face mask on during airport screening. A TSA employee will require you to adjust your mask to verify your identity.
  • Instead of handing a TSA agent your boarding pass, place it directly on the reader yourself. When that's done, hold it up for inspection.
  • One container of liquid hand sanitizer is now permitted in your carry-on luggage. It must not be larger than 12 oz (350 ml), and you'll have to take it out of your bag for scanning.
  • To minimize handling during the screening process, place items such as your phone, keys and wallet into your carry-on instead of into the bins.
  • If you're bringing food through the security checkpoint, place it in a clear plastic bag and then into a scanning bin. This reduces the likelihood that a TSA agent will need to handle your carry-on bag or food container for inspection.

Which airlines fly to Lower Matecumbe Key?
Let Delta fly you there. This prominent carrier schedules 191 services a month to Key West Intl. Airport (EYW), a Lower Matecumbe Key gateway.
How can I find cheap tickets to Lower Matecumbe Key?
Book well in advance, consider nearby airports, use miles or points — there's no shortage of ways! Another one is to take advantage of Expedia's "flexible dates" function. Find your Lower Matecumbe Key flight, then compare the cheapest prices for nearby dates. In the last seven days, the best price for a flight to Lower Matecumbe Key was .
How much is a flight to Lower Matecumbe Key?
The price of a round-trip ticket to Lower Matecumbe Key in the last seven days fluctuated between and . If you were heading one way from (), you could have landed a low-cost fare from just .
What are the most popular airports to fly into in Lower Matecumbe Key?
A major entryway to Lower Matecumbe Key, about 1119 flights land at Key West Intl. Airport (EYW) each month. Keep an eye out for an awesome deal, reserve your fare and get set to explore this wonderful region.
When is the cheapest time to fly to Lower Matecumbe Key?
Fly out on a Tuesday to boost your chances of landing the cheapest deal to Lower Matecumbe Key. Mondays are usually the second most affordable day to depart. Saturday is generally the priciest day to fly anywhere.
How much is a plane ticket to Lower Matecumbe Key?
In the last seven days, tickets to Lower Matecumbe Key fluctuated from to .
Which airlines with flights to Lower Matecumbe Key employ COVID-19 cleanliness policies?
To help lessen the contact between passengers and aircrew during the ongoing pandemic, most reputable airlines have taken physical distancing and other strategies to the skies. These carriers include:
  • 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.

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.