Upper Matecumbe Key Holidays from £979

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    Save up to £750 when you book a flight and hotel together*

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

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    Packages with flights are ATOL protected

Top Upper Matecumbe Key Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
YotelPad Miami

YotelPad Miami

4 out of 5
Downtown Miami
Price was £1,638, price is now £979 per person
£979
per person
18 Jan - 23 Jan
found 1 day ago
Return flight included
London (LON) to Miami (MIA)
8.4/10 Very good! (543 reviews)

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Price was £3,980, price is now £2,295 per person
£2,295
per person
18 Jan - 23 Jan
found 1 day ago
Return flight included
London (LON) to Miami (MIA)
9.4/10 Exceptional! (1,682 reviews)
Great Peoperty and very clean. Very friendly staff.

Reviewed on 31 Oct 2026

EAST Miami Residences

EAST Miami Residences

5 out of 5
Brickell
Price was £2,394, price is now £1,485 per person
£1,485
per person
18 Jan - 23 Jan
found 1 day ago
Return flight included
London (LON) to Miami (MIA)
9.2/10 Wonderful! (163 reviews)

EAST Miami

EAST Miami

5 out of 5
Brickell
Price was £2,151, price is now £1,356 per person
£1,356
per person
18 Jan - 23 Jan
found 1 day ago
Return flight included
London (LON) to Miami (MIA)
9.2/10 Wonderful! (4,218 reviews)

Kimpton EPIC Hotel by IHG

Kimpton EPIC Hotel by IHG

5 out of 5
Downtown Miami
Price was £1,837, price is now £1,215 per person
£1,215
per person
18 Jan - 23 Jan
found 1 day ago
Return flight included
London (LON) to Miami (MIA)
9/10 Wonderful! (2,661 reviews)

Upper Matecumbe Key Essential Information

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

Top hotels in Upper Matecumbe Key

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 £189 per night from 1 Nov to 2 Nov
£189
1 Nov - 2 Nov
includes taxes & fees
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 £160 per night from 3 Nov to 4 Nov
£160
3 Nov - 4 Nov
includes taxes & fees
Chesapeake Beach Resort
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 £186 per night from 17 Nov to 18 Nov
£186
17 Nov - 18 Nov
includes taxes & fees
Amara Cay Resort
See all 2,734 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Stay near popular Upper Matecumbe Key attractions

A marina with boats docked, a motel, and a cafe.

Bud n' Mary's Dive Center

8.8/10 (504 reviews)
Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this relaxing area.
See properties

Frequently asked questions

How much does an Upper Matecumbe Key travel package cost?
Starting from a low £979, a package is your ticket to low-priced travel. Custom build your Upper Matecumbe Key getaway by choosing from our great range of hotels, airfares and rental cars.
If I'm not able to travel, can I cancel my Upper Matecumbe Key travel package?
You can. We totally understand that things don't always go to plan, so we're here to help if you need to make changes to your Upper Matecumbe Key travel package. You may be able to change or cancel your itinerary at no cost if you've booked within 24 hours. Your hotel, airline or car rental company may impose a fee if your booking was made more than 24 hours ago. Take a look at our Customer Service Portal for more information. Also, be sure to check your itinerary for the finer details on change fees.
How do I get a cheap travel package to Upper Matecumbe Key?
It's as simple as bundling. Hotels, flights and rental cars — combine whatever you need into an Upper Matecumbe Key travel package to save tons of cash. Score even more discounts when you include extras such as day tours to your booking. But that's not the only good part. You have the freedom to put together your trip your own way. We offer over 550 air carriers and 1,000,000 properties all over the world, so that everyone has a chance to travel and live out those holiday fantasies.
Does Expedia offer Book Now, Pay Later Upper Matecumbe Key holidays?
Expedia has teamed up with online lender Klarna to make booking your next break easier on your budget. Paying by instalment means you can spread the costs of your next big adventure, leaving you with more cash to splash while you're away. Klarna has several payment plans to pick from, so you're sure to find something that fits into your budget. Consider these flexible payment options:

  • Pay monthly holidays: Klarna offers manageable monthly payment plans that work for all budgets, so you can lock in that well-earned holiday sooner.
  • Pay in instalments holidays: Into the idea of paying off your holiday in multiple transactions? Then go for this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: Clicking the "book now" button is much easier with this plan. Simply put down a small deposit on your escape and then start packing your suitcase.

How far in advance should I book my Upper Matecumbe Key holiday?
It can be hard to know when is the perfect time to book your trip to Upper Matecumbe Key. But typically the earlier you book, the more affordable the prices. Sometimes, you can lock in your flights and hotels up to 12 months prior to your departure date. If you're thinking of a last-minute getaway, no need to panic! There are fabulous deals featured on Expedia every single day.
What does an Expedia Upper Matecumbe Key travel package include?
Car rentals, flights and hotels — we bring you the very best deals. All you have to do is pick your ideal combination. Once you've made your booking, you can add on the fun stuff like activities and sightseeing tours. Our travel packages make it simple to craft an exciting Upper Matecumbe Key trip.
What should I know before booking an Upper Matecumbe Key travel package?
We already have low prices. However, you'll enjoy even more savings when you book your hotels, flights and car rentals together. With an Expedia package, you'll get transparent pricing and loads of choice.
Can I choose my airline with an Upper Matecumbe Key Expedia travel package?
With a travel package, you're the one in charge. Whether you're looking to fly to Upper Matecumbe Key in coach or first class, simply pick from the available airline options. Expedia has access to over 550 airline partners globally.

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. Flight-inclusive packages are ATOL protected.