Upper Matecumbe Key Trip

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Top Upper Matecumbe Key Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Price was ₹156,678, price is now ₹109,195 per person
₹109,195
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
16.4/10 Exceptional! (1,491 reviews)
The area was very colourful and convenient to be around.

Reviewed on 17 Nov 2025

The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Save 100% on your flight
Price was ₹309,690, price is now ₹177,925 per person
₹177,925
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
18.8/10 Exceptional! (56 reviews)
Staff super friendly and welcoming and helpful, room ready

Reviewed on 16 Nov 2025

President Hotel

President Hotel

3.5 out of 5
South Beach
Price was ₹157,017, price is now ₹109,354 per person
₹109,354
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
16.8/10 Exceptional! (1,775 reviews)
Very clean and updated. Good price. Great location!!! Other than the bed there was only a small desk and desk chair and one luggage rack. No other places to put suitcases to open them other than the bed. There was also no comfy chair to sit in to read. If you wanted to sit down there was only the small desk chair and the bed. The elevator was also very small (3 person) so during busy times it took forever to get a lift to room or to lobby. The breakfast was really good but area was very crowded. Coffee should have been out in lobby so you could get a cup before breakfast. That would also remove it from adding to the crowding in the small diningroom. The outside dining area in back had pigeons. Not real sanitary for eating in.

Reviewed on 16 Nov 2025

72 Park - Miami Beach by Nomada

72 Park - Miami Beach by Nomada

4.5 out of 5
North Beach
Price was ₹195,346, price is now ₹140,350 per person
₹140,350
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
8.8/10 Excellent! (64 reviews)
Room was so well prepared VIEW WAS AMAZING, STAFF was COURTEOUS and ATTENTIVE

Reviewed on 16 Nov 2025

Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Price was ₹169,890, price is now ₹127,614 per person
₹127,614
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
17.2/10 Exceptional! (385 reviews)
Wonderful Stay every time I come to Miami I will be there just to stay at this hotel.

Reviewed on 18 Nov 2025

Top hotels in Upper Matecumbe Key

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 ₹8,506 per night from 20 Nov to 21 Nov
₹8,506
₹14,555 total
20 Nov - 21 Nov
includes taxes & fees
9.2/10 Wonderful! (1,570 reviews)
Room was clean, breakfast and staff were good

Reviewed on 14 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 ₹18,605 per night from 16 Dec to 17 Dec
₹18,605
₹26,914 total
16 Dec - 17 Dec
includes taxes & fees
9/10 Wonderful! (1,261 reviews)
Amazing!

Reviewed on 14 Nov 2025

Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is ₹12,606 per night from 30 Nov to 1 Dec
₹12,606
₹20,065 total
30 Nov - 1 Dec
includes taxes & fees
8.8/10 Excellent! (1,258 reviews)
Rooms were clean, landscape was beautiful, staff was friendly. Access to the (2) other resorts were a plus. Would stay again.

Reviewed on 17 Nov 2025

Amara Cay Resort
See all 2,791 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.

Popular places to visit

Florida Keys Brewing Co.

Florida Keys Brewing Co.

You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.

Florida Keys Brewing Co.
Hurricane Monument which includes outdoor art and a 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

Matecumbe United Methodist Church

After visiting Matecumbe United Methodist Church, make a plan to see the other sights and activities in Islamorada. Discover the beautiful sunsets in this family-friendly area or enjoy its fishing spots.

Matecumbe United Methodist Church

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.

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