Lower Matecumbe Key Vacation Packages

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Top Lower Matecumbe Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Creekside Inn

Creekside Inn

2.5 out of 5
Price was CA $2,820, price is now CA $1,164 per person
CA $1,164
per person
Apr 7 - Apr 14
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1,004 reviews)
Room was small but clean.

Reviewed on Feb 26, 2026

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was CA $10,305, price is now CA $3,899 per person
CA $3,899
per person
May 4 - May 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
5.8/10 (311 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.

Reviewed on Feb 22, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was CA $31,552, price is now CA $14,887 per person
CA $14,887
per person
Apr 4 - Apr 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very Good! (1 review)
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
Matecumbe
Price was CA $4,357, price is now CA $2,275 per person
CA $2,275
per person
Apr 7 - Apr 14
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.6/10 Excellent! (1,000 reviews)
Room was clean, had some wear and tear but overall a good room for 5 of us. Beds were comfy. This is a quiet resort, but we did like that we could go to the other resorts. Loved the amenties. My only complaint was I wish they were available past 4pm. We wanted to do some water activities after returning to the resort but these things close early.

Reviewed on Feb 28, 2026

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Price was CA $5,206, price is now CA $2,945 per person
CA $2,945
per person
May 15 - May 22
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
My boyfriend and I had such an incredible, relaxing stay. Everyone was very nice but our front desk gentleman, Chris, really stood out. The pool was clean and the sun hit there most of the day. The bar was fun and the live music was very enjoyable. Thank you Key West Hotel. 10/10 recommend.

Reviewed on Feb 20, 2026

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Lower Matecumbe Key Hotel Deals

Matecumbe Resort

Matecumbe Resort

2 out of 5
76261 Overseas Hwy Islamorada FL
The price is CA $439 per night from Mar 6 to Mar 7
CA $439
CA $494 total
Mar 6 - Mar 7
includes taxes & fees
8.8/10 Excellent! (96 reviews)
We should have listened to reviewers! I had to wash our floors. Walls in bathroom were dusty and dirty as well as HVAC heat/air registers and ceilings had cobwebs Broken closet doors that didn’t close and occasional tiny bugs on the kitchen counter, as well as a few ants on the floor. The coffee ...

Reviewed on Feb 27, 2026

Matecumbe Resort
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
61 Hawks Cay Blvd Marathon FL
Fully refundableReserve now, pay when you stay
The price is CA $613 per night from Mar 2 to Mar 3
CA $613
CA $784 total
Mar 2 - Mar 3
includes taxes & fees
8/10 Very Good! (1,006 reviews)
We had a nice location in a 2-Bdrm premium villa that had a view of the bay. Disappointing kitchen supplies (not much silverware, bowls and pots for cooking. Basics like salt & pepper and sugars for coffee required a trek to the lobby. Front desk was not sufficiently staffed for arrivals. It tries ...

Reviewed on Feb 27, 2026

Hawks Cay Resort
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 CA $397 per night from Mar 3 to Mar 4
CA $397
CA $524 total
Mar 3 - Mar 4
includes taxes & fees
9.2/10 Wonderful! (1,659 reviews)
warm pool, beautiful view at the beach, pleasant front desk and breakfast staff

Reviewed on Feb 28, 2026

Chesapeake Beach Resort
See all 2,144 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.
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Discover the most popular places to visit in Lower Matecumbe Key

Anne\'s Beach featuring a bridge

Anne's Beach

If a restful vacation is part of your travel plans, Anne's Beach might be the perfect place to seek out during your trip to Islamorada.

Anne's 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 canceling 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 travelers 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 traveling 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.

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