Upper Matecumbe Key Vacation Packages

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Top Upper Matecumbe Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
President Hotel Villa

President Hotel Villa

3.5 out of 5
South Beach
Price was CA $1,354, price is now CA $785 per person
CA $785
per person
May 25 - May 30
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.2/10 Very Good! (1,001 reviews)
The breakfast is worth the book, its nothing to fancy but definitely worth getting. The area is close to a bus stop and othet amenities nearby. If i was to come back to miami id definitely book again

Reviewed on Apr 1, 2026

Creekside Inn

Creekside Inn

2.5 out of 5
Price was CA $3,101, price is now CA $1,341 per person
CA $1,341
per person
May 10 - May 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
7.8/10 Good! (1,002 reviews)
We had an excellent stay!

Reviewed on Mar 31, 2026

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was CA $6,139, price is now CA $3,036 per person
CA $3,036
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
5.8/10 (321 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

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was CA $3,155, price is now CA $1,839 per person
CA $1,839
per person
Jun 12 - Jun 19
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.6/10 Excellent! (1,007 reviews)
Clean room , friendly staff , bar , and nearby restaurant and the beach. For parking there’s a garage $20 for 24hrs GREAT Deal.

Reviewed on Apr 2, 2026

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Price was CA $5,190, price is now CA $3,028 per person
CA $3,028
per person
May 25 - May 30
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9.4/10 Exceptional! (1,464 reviews)
One of the Best hotels I stayed at

Reviewed on Apr 1, 2026

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Upper Matecumbe Key Hotel Deals

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 $382 per night from Apr 22 to Apr 23
CA $382
CA $531 total
Apr 22 - Apr 23
includes taxes & fees
9.2/10 Wonderful! (1,304 reviews)
From the moment we checked in with Jessica we knew we’d love Cheeca lodge. Great pools, fishing dock and rooms, along with the friendliest staff

Reviewed on Apr 1, 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 CA $287 per night from May 4 to May 5
CA $287
CA $401 total
May 4 - May 5
includes taxes & fees
9.2/10 Wonderful! (1,678 reviews)
Everything about our stay here was fantastic! The staff were all very friendly and accommodating. Fresh-made omelets with friendly smiles to start every day! Everything was very clean. We will be back!

Reviewed on Apr 2, 2026

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is CA $397 per night from May 3 to May 4
CA $397
CA $548 total
May 3 - May 4
includes taxes & fees
8.8/10 Excellent! (1,261 reviews)
Great

Reviewed on Mar 30, 2026

Amara Cay Resort
See all 2,787 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.
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Discover the most popular places to visit in Upper Matecumbe Key

History of Diving Museum

History of Diving Museum

Trace one of the world’s most astonishing watersports back through the centuries to see some of the first diving suits as you explore this interactive museum, featuring the world's largest international collection of diving artifacts.

History of Diving Museum
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 travelers 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 vacation 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.
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.

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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.