Upper Matecumbe Key Holidays from £695

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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.
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
per person
11 Sept - 15 Sept
found 1 day ago
Return flight included
London (LON) to Miami (MIA)
9.4/10 Exceptional! (8 reviews)
Stayed at the new Shelbourne Hotel in Miami Beach and honestly everything was great. The front desk staff was super friendly and helpful, which set the tone right away. The pool was calm and peaceful—such a nice vibe. Everything felt fresh and clean. Definitely would come back.

Reviewed on 31 Jul 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
4 Oct - 11 Oct
found 23 hours ago
Return flight included
London (LHR) to Miami (MIA)
8/10 Very Good! (1 review)
Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
per person
18 Oct - 25 Oct
found 1 day ago
Return flight included
London (LON) to Miami (MIA)
8.6/10 Excellent! (1,154 reviews)
The food options weren’t the best. Very pricey and not many options. The beds were very comfy though.

Reviewed on 3 Aug 2025

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
per person
4 Oct - 11 Oct
found 22 hours ago
Return flight included
London (LHR) to Miami (MIA)
9.4/10 Exceptional! (1,212 reviews)
Great eco ambience, wonderful residence, direct access to beach and quiet

Reviewed on 2 Aug 2025

EAST Miami Residences

EAST Miami Residences

5 out of 5
Downtown Miami
Save 100% on your flight
per person
4 Oct - 11 Oct
found 8 hours ago
Return flight included
London (LHR) to Miami (MIA)
9/10 Wonderful! (64 reviews)
No me gustó el sector ya que hay mucho ruido en la calle motos carros acelerando No deja dormir La habitación me gustó bastante pero no logré Disfrutarla

Reviewed on 23 May 2025

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, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is £191 per night from 13 Aug to 14 Aug
£191
13 Aug - 14 Aug
includes taxes & fees
9/10 Wonderful! (1,139 reviews)
"Restaurant options are great, they offer Italian, sushi, beachside dining and an American restaurant. There are also poolside versions of their regular American restaurant. The amenities are phenomenal, including pier fishing, bikes, games and various water sport activities. There are plenty of other ..."

Reviewed on 2 Aug 2025

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 £155 per night from 28 Aug to 29 Aug
£155
28 Aug - 29 Aug
includes taxes & fees
9/10 Wonderful! (1,479 reviews)
"-"

Reviewed on 31 Jul 2025

Chesapeake Beach Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is £227 per night from 11 Aug to 12 Aug
£227
11 Aug - 12 Aug
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"Awesome Resort, great staff and helpful management. Definitely will be coming back here."

Reviewed on 1 Aug 2025

Islander Resort
See all 2,807 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

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.

Frequently asked questions

How much does an Upper Matecumbe Key travel package cost?
Starting from a low £695, 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.

* 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.