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 $2,030, price is now CA $1,112 per person
CA $1,112
per person
May 28 - Jun 1
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
7.8/10 Good! (1,002 reviews)
I stay here twice a year, love it. Cheap, great location. If you’re not picky, this is not for you.

Reviewed on Apr 12, 2026

Miami Downtown Condos

Miami Downtown Condos

5 out of 5
Downtown Miami
Price was CA $3,131, price is now CA $1,412 per person
CA $1,412
per person
Jun 27 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
8.2/10 Very Good! (135 reviews)
Everybody was very nice, helpful and friendly they answered All my questions right away helped me right away the condo was so clean and nice my balcony loved it beautiful view I’m definitely coming back they get 10 stars from go book them I asked for a late check out they answered right away and gave it to me I love them I’m definitely coming back

Reviewed on Apr 14, 2026

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was CA $7,876, price is now CA $3,873 per person
CA $3,873
per person
Jun 5 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
5.8/10 (322 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 $15,970, price is now CA $8,952 per person
CA $8,952
per person
May 23 - May 26
found 23 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very Good! (1 review)
Brickell Sea View 2BR Free Parking by Palermo Home

Brickell Sea View 2BR Free Parking by Palermo Home

2.5 out of 5
Brickell
Price was CA $6,002, price is now CA $3,394 per person
CA $3,394
per person
Jun 27 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
10/10 Exceptional! (1 review)

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Lower Matecumbe Key Hotel Deals

Matecumbe Resort

Matecumbe Resort

2 out of 5
76261 Overseas Hwy Islamorada FL
8.8/10 Excellent! (115 reviews)
Very nice pool area.

Reviewed on Apr 15, 2026

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Matecumbe Resort
Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay

3 out of 5
73801 Overseas Hwy Islamorada FL
Get rates
Caloosa Cove Resort by CoolVacay
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 CA $375 per night from May 3 to May 4
CA $375
CA $522 total
May 3 - May 4
includes taxes & fees
9.2/10 Wonderful! (1,318 reviews)
The rooms we were in were definitely tired with thin walls. You could hear everything in the room next door. The golf course lodging probably needs to be torn down and rebuilt. The property/location was great and the staff were super friendly.

Reviewed on Apr 12, 2026

Cheeca Lodge & Spa
See all 2,123 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

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.