Upper Matecumbe Key Holidays from AU$2,580

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The Latest Upper Matecumbe Key Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Key West Historic District
Save 100% on your flight
Price was AU$4,446, price is now AU$2,580 per person
AU$2,580
per person
15 Feb - 21 Feb
found 23 hours ago
Return flight included
Louisville (SDF) to Key West (EYW)
9.2/10 Wonderful! (845 reviews)
Room was clean, staff were awesome.

Reviewed on 27 Nov 2025

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
Price was AU$5,746, price is now AU$3,030 per person
AU$3,030
per person
15 Feb - 21 Feb
found 23 hours ago
Return flight included
Louisville (SDF) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
Clean room, staff, breakfast

Reviewed on 25 Nov 2025

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Old Town Key West
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Price was AU$5,657, price is now AU$2,987 per person
AU$2,987
per person
15 Feb - 21 Feb
found 23 hours ago
Return flight included
Louisville (SDF) to Key West (EYW)
9.4/10 Exceptional! (390 reviews)
Everything was great. Staff were all super helpful. Location fantastic. Breakfast served outside the room on the verander we loved (the health shots were a lovely touch). We had a great stay. Would definitely recommend.

Reviewed on 22 Nov 2025

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Price was AU$8,710, price is now AU$4,818 per person
AU$4,818
per person
15 Feb - 21 Feb
found 23 hours ago
Return flight included
Louisville (SDF) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Beautiful private oasis

Reviewed on 25 Nov 2025

The Gardens Hotel

The Gardens Hotel

4 out of 5
Old Town Key West
Save 100% on your flight
Price was AU$6,292, price is now AU$3,691 per person
AU$3,691
per person
15 Feb - 21 Feb
found 23 hours ago
Return flight included
Louisville (SDF) to Key West (EYW)
9.8/10 Exceptional! (1,000 reviews)
Great breakfast, convenient location. Staff is very friendly. Rooms are nice and the garden area is pretty. I read all of the reviews and the hype around the place so it fell short of my expectations. If I had just gone there and not read the reviews I may have enjoyed it more. I would go back but I had stayed at places as nice or nice for my needs for what I believe to be better value. That being said I am glad I stayed there

Reviewed on 20 Nov 2025

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Upper Matecumbe Key Holiday

Upper Matecumbe Key Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)

Our pick of the best 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 AU$310 per night from 7 Dec to 8 Dec
AU$310
7 Dec - 8 Dec
includes taxes & fees
9.2/10 Wonderful! (1,582 reviews)
Beautiful resort with lots of included activities & water sports. Friendly staff. Clean rooms.

Reviewed on 17 Nov 2025

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 AU$462 per night from 10 Dec to 11 Dec
AU$462
10 Dec - 11 Dec
includes taxes & fees
9/10 Wonderful! (1,274 reviews)
This was a great property. Numerous dining options. I was so impressed with the grouper sandwich, possibly the best that I’ve eaten in 30 years in Florida and the Florida Keys. The customer service staff was amazing and so thorough informing guest at check-in of all of the amenities available to ...

Reviewed on 23 Nov 2025

Cheeca Lodge & Spa
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 AU$347 per night from 1 Dec to 2 Dec
AU$347
1 Dec - 2 Dec
includes taxes & fees
8.8/10 Excellent! (1,268 reviews)
Loved the resort

Reviewed on 21 Nov 2025

Amara Cay Resort
See all 2,838 properties in Upper Matecumbe Key
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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 travellers 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 holiday 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.