Upper Matecumbe Key Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Cameron Abbott

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Upper 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 $1,716, price is now CA $989 per person
CA $989
per person
May 28 - May 31
found 19 hours ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
7.8/10 Good! (1,027 reviews)
We enjoyed our stay at Creekside Inn and it was in a beautiful location. The only downside is that the staff were only available for limited hours during the day. After hours, we could not reach anyone at the phone number posted on the office door.

Reviewed on Mar 25, 2026

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was CA $10,482, price is now CA $4,328 per person
CA $4,328
per person
May 5 - May 12
found 13 hours ago
Roundtrip flight included
Toronto (YTO) 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

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Price was CA $5,571, price is now CA $3,261 per person
CA $3,261
per person
Jun 11 - Jun 16
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
9.4/10 Exceptional! (1,464 reviews)
This hotel is so beautiful and the staff is so kind and accommodating. The pool and beach areas are stunning, the food is delicious, the rooms are spacious, the beds are so comfortable, and the location is perfect. It’s the best hotel experience I’ve ever had, and I can’t wait to go back again!

Reviewed on Mar 7, 2026

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Price was CA $2,008, price is now CA $1,205 per person
CA $1,205
per person
Apr 26 - May 2
found 2 days ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.2/10 Very Good! (1,725 reviews)
Clean room , comfy bed . Nice pool , excellent location , nice front patio to sit at and great margaritas at the bar !

Reviewed on Mar 20, 2026

Ready to book your vacation to Upper Matecumbe Key?

 

Choose your dates

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 $489 per night from Apr 13 to Apr 14
CA $489
CA $651 total
Apr 13 - Apr 14
includes taxes & fees
9.2/10 Wonderful! (1,301 reviews)
They should have had a newsletter with activities.

Reviewed on Mar 23, 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 $339 per night from Apr 14 to Apr 15
CA $339
CA $458 total
Apr 14 - Apr 15
includes taxes & fees
9.2/10 Wonderful! (1,675 reviews)
The room was great! Clean and up to date. The staff was very accomadating abd the view was beautiful. Breakfast was more than enough and it was located close to everything.

Reviewed on Mar 24, 2026

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is CA $379 per night from Apr 12 to Apr 13
CA $379
CA $528 total
Apr 12 - Apr 13
includes taxes & fees
8.8/10 Excellent! (1,260 reviews)
Friendly welcome and great room size. Communal areas are beautifully decorated!

Reviewed on Mar 23, 2026

Amara Cay Resort
See all 2,806 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Upper Matecumbe Key

History of Diving Museum showing heritage elements

History of Diving Museum

4/5(1 review)

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 showing outdoor art and a monument

Hurricane Monument

4/5(1 review)

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.

Explore a world of travel with Expedia

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