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.
Brickell Bay 3318

Brickell Bay 3318

3 out of 5
Brickell
Price was CA $2,365, price is now CA $1,088 per person
CA $1,088
per person
Jul 10 - Jul 14
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
No reviews
MirabileCondoDwntown MIA Brickell w PRKG

MirabileCondoDwntown MIA Brickell w PRKG

5 out of 5
Downtown Miami
Price was CA $3,498, price is now CA $1,482 per person
CA $1,482
per person
Jul 19 - Jul 24
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
2/10 (2 reviews)
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 $50,245, price is now CA $25,829 per person
CA $25,829
per person
Jun 23 - Jun 30
found 1 day ago
Roundtrip flight included
Montreal Metropolitan Airport (YHU) to Miami (MIA)
8/10 Very Good! (1 review)
The Landon Bay Harbor - Miami Beach

The Landon Bay Harbor - Miami Beach

3.5 out of 5
Price was CA $7,419, price is now CA $4,015 per person
CA $4,015
per person
Jun 25 - Jul 2
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.2/10 Very Good! (1,011 reviews)
Property was moderately nice; no thrills.

Reviewed on May 12, 2026

The W - Bayshore Unit 1003

The W - Bayshore Unit 1003

3 out of 5
East Fort Lauderdale
Price was CA $2,048, price is now CA $1,132 per person
CA $1,132
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
6/10 (2 reviews)

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Upper Matecumbe Key Hotel Deals

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 $243 per night from Jun 18 to Jun 19
CA $243
CA $351 total
Jun 18 - Jun 19
includes taxes & fees
9.2/10 Wonderful! (1,729 reviews)
"Kayak, pools and breakfast were awesome"

Reviewed on May 17, 2026

Chesapeake Beach 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 $373 per night from Jun 1 to Jun 2
CA $373
CA $520 total
Jun 1 - Jun 2
includes taxes & fees
9.2/10 Wonderful! (1,314 reviews)
"checkin was bumpy. both rooms werent ready at the same time and we were initially put into different building. I objected and they obliged but still had to wait for 2nd room either way. 1st room in furthest corner of resort, fan broken, a/c was repaired during 1st night & also the sliding door lock ..."

Reviewed on May 17, 2026

Cheeca Lodge & Spa
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is CA $290 per night from May 31 to Jun 1
CA $290
CA $419 total
May 31 - Jun 1
includes taxes & fees
9.2/10 Wonderful! (1,015 reviews)
"Yes"

Reviewed on May 16, 2026

Islander Resort
See all 2,812 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.