Upper Matecumbe Key Trip

Book a Hotel + Flight or Car together to unlock savings

Photo by Cameron Abbott

  • Plan, book, travel with confidence

  • Better together

    Save up to ₹43,962 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 Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
President Hotel Villa

President Hotel Villa

3.5 out of 5
South Beach
Price was ₹157,621, price is now ₹79,446 per person
₹79,446
per person
28 Mar - 3 Apr
found 1 day ago
Return flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (997 reviews)
Room was clean only had a problem with the toilet it took them awhile to come fix it the breakfast was good and staff definitely did everything they could to make our stay comfortable even until check out they held our bags for us because we had a later flight from our check out.

Reviewed on 15 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 ₹2,349,859, price is now ₹1,085,870 per person
₹1,085,870
per person
28 Mar - 3 Apr
found 1 day ago
Return flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was ₹190,925, price is now ₹90,275 per person
₹90,275
per person
28 Mar - 3 Apr
found 1 day ago
Return flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Lets be clear, you stay here for the location and the art deco building. Amenities are just OK. Staff is friendly but rooms are dated. Sofa bed for my 2 daughters was broken (room 301). No common area (lounge to seat down and relax), it is all restaurant. So this is one of those “been there donde that” kind of places. Next time either a B&B or a large chain hotel.

Reviewed on 17 Feb 2026

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Price was ₹157,794, price is now ₹79,519 per person
₹79,519
per person
28 Mar - 3 Apr
found 1 day ago
Return flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,491 reviews)
The room was very clean and the staff was very friendly.

Reviewed on 16 Feb 2026

President Hotel

President Hotel

3.5 out of 5
South Beach
Price was ₹157,621, price is now ₹79,446 per person
₹79,446
per person
28 Mar - 3 Apr
found 1 day ago
Return flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,775 reviews)
The room was spotless and staff was courteous. Food was good and had enough places to sit. The atmosphere was very relaxed and the staff was willing to help with any need.

Reviewed on 17 Feb 2026

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 ₹35,181 per night from 1 Mar to 2 Mar
₹35,181
₹44,677 total
1 Mar - 2 Mar
includes taxes & fees
9.2/10 Wonderful! (1,663 reviews)
Great staff, especially front desk and breakfast chefs!!! Beautiful facilty-laid back vibe just as it should be on the Keys!!!

Reviewed on 17 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 ₹29,614 per night from 22 Feb to 23 Feb
₹29,614
₹39,945 total
22 Feb - 23 Feb
includes taxes & fees
9.2/10 Wonderful! (1,305 reviews)
Place was great! Staff was amazing. Jessica at the front desk is a Rockstar! Property was beautiful!

Reviewed on 15 Feb 2026

Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is ₹31,913 per night from 25 Feb to 26 Feb
₹31,913
₹42,532 total
25 Feb - 26 Feb
includes taxes & fees
8.8/10 Excellent! (1,256 reviews)
room was clean people were nice . was concerned being on the fifth floor and drone flying outside every day. felt weird like invasion of privacy.

Reviewed on 16 Feb 2026

Amara Cay Resort
See all 2,819 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. showing signage

Florida Keys Brewing Co.

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

Florida Keys Brewing Co.
Islamorada_MatecumbeUnitedMethodistChurch_553248621532652347-0004

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
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

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.

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.