Upper Matecumbe Key Holidays from £957
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Top Upper Matecumbe Key Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
£5,831
per person
25 Oct - 29 Oct
found 1 day ago
Return flight included
London (LHR) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on 22 Jun 2016
Cavalier Hotel South Beach
South Beach
£1,093
per person
30 Nov - 7 Dec
found 1 day ago
Return flight included
London (LHR) to Miami (MIA)
8.6/10 Excellent! (1,005 reviews)
Estuvo muy bueno. Lo malo es que te enganchan las sillas pero sin las sombrillas y ahí esta el truco. De resto todo muy
Reviewed on 13 Sept 2026
Hotel Riu Plaza Miami Beach
Mid Beach
£1,338
per person
30 Nov - 7 Dec
found 1 day ago
Return flight included
London (LHR) to Miami (MIA)
8.2/10 Very good! (1,180 reviews)
When we first arrived at the hotel the staff Clariza or Clarisa was very rude and disrespectful. She told us about a reservation fee and I asked for more clarification regarding that fee. She got smart and snatched the card and said it’s $165 along with a $250 deposit.
Reviewed on 15 Sept 2026
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
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
£167
29 Sept - 30 Sept
includes taxes & fees
9.2/10 Wonderful! (1,440 reviews)
"Clean and comfortable rooms, but I did get a dated feel, but certainly served our purpose. The property supplied EVERYTHING needed to enjoy your stay. I didn’t have dinner there, but their breakfast was elevated and delish. The Adult pool we used had an exercise instructor, a spa and was crystal ..."
Reviewed on 14 Sept 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
£165
20 Sept - 21 Sept
includes taxes & fees
9.2/10 Wonderful! (1,780 reviews)
"/"
Reviewed on 13 Sept 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
£171
27 Sept - 28 Sept
includes taxes & fees
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.
Stay near popular Upper Matecumbe Key attractions
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.
Florida Keys Brewing Co.
9.2/10 (520 reviews)
You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.
History of Diving Museum
9.0/10 (177 reviews)
Trace one of the world’s most astonishing watersports back through the centuries to see some of the first diving suits as you explore this interactive museum, featuring the world's largest international collection of diving artifacts.
Islamorada Brewery & Distillery
9.4/10 (8 reviews)
You can take time to visit Islamorada Brewery & Distillery during your travels to Islamorada.
Lorelei Restaurant & Cabana Bar
After visiting Lorelei Restaurant & Cabana Bar, make a plan to see the other sights and activities in Islamorada.
MoradaWay Arts & Cultural District
Enjoy an outing to MoradaWay Arts & Cultural District during your stay in Islamorada.
beach near Islamorada
Why not spend a lazy afternoon at beach near Islamorada during your trip to Islamorada?
Keys History & Discovery Center
You can spend time studying the exhibits at Keys History & Discovery Center during your trip to Islamorada.
Frequently asked questions
How much does an Upper Matecumbe Key travel package cost?
Starting from a low £957, 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
- 5 Star Hotels in Duck Key
- 5 Star Hotels in Islamorada
- 5 Star Hotels in Key Largo
- Hotels near Harry Harris Park
- Beach Resorts & in Islamorada
- Beautiful Home in a Great Neighborhood with Ocean Access and Boat Ramp on Property
- Cheap Hotels in Islamorada
- Family-Friendly Hotels in Islamorada
- Sleeps 8
- Hotels Suites in Islamorada
- Hotels with a Bar in Islamorada
- Hotels with Connecting Rooms in Islamorada
- Hotels with Hot Tubs in Islamorada
- Isla Honeydew
- Isla Lychee
- Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!
- Bayside Villas by Islander Resort
- Luxury Hotels in Islamorada
- Three Waters Resort and Marina
- Islamorada Hotels
- Hotels near Jimmy Johnson's Big Chill
- 124 Mariners Club
- 200ft of Waterfront with Tiki & Heated Pool
- Spectacular Oceanfront Views 3 bed/bath Villa with Amazing Views!
- 3bed vacation ocean side townhome 2pools
- 403 Mariners Club
- All-Inclusive Hotels in Key Largo
- Beach Resorts & in Key Largo
- Mariners Club Townhouse
- Cheap Hotels in Key Largo
- Family-Friendly Hotels in Key Largo
- Florida Keys canal front Vacation Home
- Gay-Friendly Hotels in Key Largo
- Island Paradise with private beach & private bay sunset views.
- Kawama Yacht Club
- Key Largo 3 Bedroom Penthouse Condo with Boat Slip and Bay View
- Pennekamp Hideaway
- Full TIME LIC MGR
- Mariner's Club Key Largo by KeysCaribbean
- Oceanfront 2BR/2.5BA Mariner's Club Villa 512 with Oasis Pool
- Paradise Cove-1stFloor- Key Largo
- Premium Floating Bugalow by Stay Ombi in the Keys with Stunning Ocean Views.
- Private Beach Bayside 6 Bedroom Resort Home with Pool
- Reefhouse Resort & Marina
- Marina Vista Gem • Modern 2BR/2BA • Steps to Pickleball
- Sunrise Escape
- New! CASA AZUL OCEANSIDE
- Key Largo Hotels
- Layton Hotels
- Long Key Hotels
- Matecumbe Hotels
- Key Largo Baha Penthouse Ocean Pointe 1416
- Modern and Coastal Ocean Pointe 2307
- Ocean Oasis at Ocean Pointe Key Largo Pool Jacuzzi Beach in a Safe Gated Resort
- New Ocean Pearl • Beach • Restaurant • Pickleball • Marina
- Whispering Palms
- Tavernier Hotels
- Big Pine Key Holidays
- Calusa Beach
- Curry Hammock State Park
- Dadeland Mall
- Visit Duck Key
- Everglades National Park
- Florida City Holidays
- Homestead Air Force Base
- Homestead Holidays
- Islamorada Holidays
- Visit Islamorada
- Jimmy Johnson's Big Chill
- Kendall Holidays
- Key Largo Holidays
- Visit Key Largo
- Visit Layton
- Visit Long Key
- Marathon Holidays
- Matheson Hammock Park
- Visit Plantation Key
- Sombrero Beach
- Visit Tavernier
- Visit Upper Matecumbe Key
- Vaca Key
- Zoo Miami
* 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.
