Upper Matecumbe Key Holidays from AU$1,148

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The Latest Upper Matecumbe Key Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
Price was AU$2,121, price is now AU$1,148 per person
AU$1,148
per person
2 Apr - 6 Apr
found 16 hours ago
Return flight included
Nashville (BNA) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Loved the location, room was nice, bathroom very small, very friendly staff, slow service at restaurant in the morning. Will go back

Reviewed on 24 Feb 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 AU$32,491, price is now AU$16,868 per person
AU$16,868
per person
2 Apr - 6 Apr
found 16 hours ago
Return flight included
Nashville (BNA) to Miami (MIA)
8/10 Very Good! (1 review)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
Price was AU$7,406, price is now AU$4,586 per person
AU$4,586
per person
2 Apr - 6 Apr
found 16 hours ago
Return flight included
Nashville (BNA) to Miami (MIA)
9.4/10 Exceptional! (1,365 reviews)
The room was spacious and staffs were warm too

Reviewed on 20 Feb 2026

Carillon Miami Wellness Resort

Carillon Miami Wellness Resort

5 out of 5
North Beach
Save 100% on your flight
Price was AU$4,488, price is now AU$2,798 per person
AU$2,798
per person
2 Apr - 6 Apr
found 16 hours ago
Return flight included
Nashville (BNA) to Miami (MIA)
8.8/10 Excellent! (765 reviews)
The staff were so so nice! The hotel was so clean and so green and so cool and I loved every minute of it

Reviewed on 5 Feb 2026

Bentley Hotel South Beach

Bentley Hotel South Beach

4 out of 5
South Beach
Save 100% on your flight
Price was AU$3,375, price is now AU$2,143 per person
AU$2,143
per person
2 Apr - 6 Apr
found 16 hours ago
Return flight included
Nashville (BNA) to Miami (MIA)
9.2/10 Wonderful! (466 reviews)
The hotel was exceptionally clean. Staff very friendly and helpful. The breakfast was also nice.

Reviewed on 26 Feb 2026

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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$569 per night from 1 Mar to 2 Mar
AU$569
1 Mar - 2 Mar
includes taxes & fees
9.2/10 Wonderful! (1,654 reviews)
Nice clean spacious room.Beautiful location overlooking the water.Staff was eager to please

Reviewed on 24 Feb 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 AU$1,086 per night from 27 Feb to 28 Feb
AU$1,086
27 Feb - 28 Feb
includes taxes & fees
9.2/10 Wonderful! (1,297 reviews)
This Resort is unbelievable from the rooms to the beach, walking & biking trails, golf course 27 acres of lush property. Lots of shops & restaurants nearby including Bass Pro Shop, small artists shops & brewery within walking/biking distance.

Reviewed on 25 Feb 2026

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$563 per night from 1 Mar to 2 Mar
AU$563
1 Mar - 2 Mar
includes taxes & fees
8.8/10 Excellent! (1,266 reviews)
Room had a musty odor. Tiki bar staff non attentive. Grounds were beautiful

Reviewed on 22 Feb 2026

Amara Cay Resort
See all 2,803 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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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.