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.
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
Price was CA $2,380, price is now CA $1,338 per person
CA $1,338
per person
Aug 10 - Aug 17
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Key West (EYW)
8/10 Very good! (2,313 reviews)
Breakfast needs improvement because it lacks variety.

Reviewed on Jun 24, 2026

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was CA $12,121, price is now CA $5,770 per person
CA $5,770
per person
Jul 26 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
5.8/10 (324 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

Girasole Apartments

Girasole Apartments

3.5 out of 5
Mid Beach
Price was CA $6,160, price is now CA $3,199 per person
CA $3,199
per person
Aug 3 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
6.4/10 (837 reviews)
Una ubicación perfecta frente al Mar.

Reviewed on Jun 14, 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 $27,335, price is now CA $15,626 per person
CA $15,626
per person
Jul 27 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very good! (1 review)
Pantera Rosa

Pantera Rosa

4 out of 5
South Beach
Price was CA $2,257, price is now CA $1,420 per person
CA $1,420
per person
Sep 3 - Sep 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8.8/10 Excellent! (72 reviews)
Excellent experience, great accommodation no issues

Reviewed on Jun 23, 2026

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Lower Matecumbe Key Hotel Deals

Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay

3 out of 5
73801 Overseas Hwy Islamorada FL
The price is CA $395 per night from Jul 1 to Jul 2
CA $395
CA $492 total
Jul 1 - Jul 2
includes taxes & fees
9.8/10 Exceptional! (6 reviews)
"We had a great stay! The view is amazing. You are right on the water. Pool was clean and heated. A couple of restaurants you can walk too. Will probably stay here again!"

Reviewed on Jun 21, 2026

Caloosa Cove Resort by CoolVacay
Matecumbe Resort

Matecumbe Resort

2 out of 5
76261 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is CA $216 per night from Jul 7 to Jul 8
CA $216
CA $243 total
Jul 7 - Jul 8
includes taxes & fees
9/10 Wonderful! (145 reviews)
"Had a wonderful stay with them. They had everything you could want and at a great price. Will be beck for sure!"

Reviewed on Jun 25, 2026

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 CA $322 per night from Jul 19 to Jul 20
CA $322
CA $467 total
Jul 19 - Jul 20
includes taxes & fees
9.2/10 Wonderful! (1,324 reviews)
"The decor was updated a bit but then dated in other areas. The balcony cushions had stains and the carpet needed to be replaced."

Reviewed on Jun 23, 2026

Cheeca Lodge & Spa
See all 2,092 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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Stay near popular Lower Matecumbe Key attractions

Anne's Beach

7.8/5 (597 reviews)
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.
See properties

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.