Upper Matecumbe Key Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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 easyPlan, book, and manage your trip all in one place
Top Upper Matecumbe Key Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Avi Lux Stay
East Fort Lauderdale
CA $1,498
per person
Nov 16 - Nov 23
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
7.6/10 Good! (10 reviews)
If you are looking for a quiet place to stay this suite is NOT recommended. You can hear motorcycles and racing cars at all hours of the night. Valet is $60 per night mandatory payment required upon check in for the entire length of your stay tips not included. This is not stated in the description prior to booking. BEWARE.
Reviewed on Aug 28, 2025
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $25,652
per person
Dec 23 - Dec 28
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) 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 Jun 22, 2016
The Penguin Hotel
South Beach
CA $1,587
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.4/10 Very good! (1,996 reviews)
There is a resort fee per day, on top of 150 they need for the room Just an fyi. The front desk ladies were very helpful and nice but the one of the over night men couldn’t have a worse attitude up front I wish I got his name. The pool closes at 7 and it’s not located at this hotel it’s at the building behind it and the bar is also located not actually at this hotel. Elevator worked but very loud so we heard it every time it went up or down. And the walls are paper thin so it didn’t help.They say it’s every 3 days they clean but knocked on our door every morning and the lady was very friendly. Wasn’t the worst hotel I’ve stayed in but I don’t think I’ll be back. Only plus is the location because the beach being across the street
Reviewed on Oct 15, 2026
Ready to book your vacation to Upper Matecumbe Key?
Upper Matecumbe Key Hotel Deals
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
CA $237
CA $371 total
Oct 22 - Oct 23
includes taxes & fees
9.2/10 Wonderful! (1,480 reviews)
"Loved the property, staff and rooms"
Reviewed on Oct 16, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
CA $195
CA $299 total
Oct 18 - Oct 19
includes taxes & fees
9.4/10 Exceptional! (1,796 reviews)
"Excellent location we had a Waterview room, which was extremely clean well maintained with a beautiful view of the ocean and beach from our balcony. Both swimming pools were well maintained. Only glitch was hot tub was not working.. would definitely stay again ."
Reviewed on Oct 16, 2026
Islander Resort
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
CA $277
CA $415 total
Nov 15 - Nov 16
includes taxes & fees
9.4/10 Exceptional! (1,143 reviews)
"Very nice experience and cosy hotel in the Keys, super recommended!"
Reviewed on Oct 16, 2026
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.
Hurricane Monument
8.6/10 (250 reviews)
The memories of those lost to the 1935 Labor Day Hurricane live on at this moving tribute and burial site along the Overseas Highway.
Islamorada Brewery & Distillery
9.4/10 (8 reviews)
You can take time to visit Islamorada Brewery & Distillery during your travels to Islamorada.
beach near Islamorada
Why not spend a lazy afternoon at beach near Islamorada during your trip to Islamorada?
MoradaWay Arts & Cultural District
Enjoy an outing to MoradaWay Arts & Cultural District during your stay in Islamorada.
Lorelei Restaurant & Cabana Bar
After visiting Lorelei Restaurant & Cabana Bar, make a plan to see the other sights and activities in Islamorada.
Frequently asked questions
How much does an Upper Matecumbe Key vacation package cost?
Starting from a low CA $1,498, a package is your passport to low-cost travel. Custom make your Upper Matecumbe Key getaway by selecting from our huge range of hotels, airfares and rental cars.
How do I get a cheap travel package to Upper Matecumbe Key?
You'll save loads of cash if you combine your hotels, flights and car rentals into an Upper Matecumbe Key vacation package. Sometimes cheap packages mean fewer choices. But that's not the case with Expedia. We offer more than 550 partner airlines and 1,000,000 properties throughout the world, so you'll always have plenty of variety to choose from. Eager to save even more? Add some exciting activities to your package deal to unlock even more discounts! After all, travel is about more than simply getting to your destination.
How far in advance should I book my Upper Matecumbe Key vacation?
While prices change frequently, we generally suggest booking your spot as soon as possible. Many international airfares are available on Expedia up to a year in advance. If you're booking late, you may still get lucky. Cheap tickets to Upper Matecumbe Key sometimes appear just weeks before departure.
What does an Expedia Upper Matecumbe Key travel package include?
Flights, car rentals and hotels — we connect you to the very best bargains. All you'll have to do is figure out your preferred combination. After you've made your booking, you can add on the fun stuff like sightseeing activities. Our travel packages make it easy to put together an exciting Upper Matecumbe Key escape.
What should I know before booking an Upper Matecumbe Key travel package?
We already have low prices. However, you'll enjoy an even better deal if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and loads of choice.
Can I choose my airline with an Upper Matecumbe Key Expedia vacation package?
Yes — that's one of the best things about an Expedia vacation package. You're in control. We have access to more than 550 airline partners worldwide, so you have lots of choice when putting together your Upper Matecumbe Key adventure.
If I'm not able to travel, can I cancel my Upper Matecumbe Key vacation package?
You sure can, and we'll help you every step of the way. You may be able to amend or cancel your Upper Matecumbe Key vacation package for free within 24 hours of booking. However, you may be charged a fee by your hotel, airline or car rental company for older bookings. If your travel plans unexpectedly change, look up our Customer Service Portal for more information.
Explore a world of travel with Expedia
- Hersha Hospitality Hotels in Upper Matecumbe Key
- Tropical Escape
- Hotels with Waterslides in Islamorada
- Motels in Islamorada
- Key Largo Hotels
- Family Hotels in Islamorada
- Tavernier Hotels
- Beach Hotel Hotels in Key Largo
- Houseboats in Windley Key
- Long Key Hotels
- Cheap Hotels in Islamorada
- Rv Parks in Lower Matecumbe Key
- All Inclusive Resorts and in Islamorada
- Amoray Dive Resort
- Matecumbe Hotels
- Hotels near Everglades National Park
- Wyndham Hotels in Islamorada
- Stunning Direct Ocean Views from 2BR Suite
- Hotels with smoking rooms in Islamorada
- Beach Hotel Hotels in Long Key
- Beach Hotel Hotels in Islamorada
- Hotels with Free Airport Shuttle in Islamorada
- Family Hotels in Key Largo
- Luxury Hotels in Islamorada
- Port Antigua Retreat on Canal with Boat Lift and Private Beach Access
- Inns in Islamorada
- Oceanfront Hotels in Islamorada
- Resorts in Upper Matecumbe Key
- Vacation Homes in Layton
- Barefoot Bliss
- Layton Hotels
- Apartments in Layton
- Waterfront Home With Swimming Pool
- B&B in Tavernier
- Direct Oceanfront with private staircase to beach prestigious Islamorada CondoComplex
- All Inclusive Resorts and in Key Largo
- Fish
- Best Western Hotels in Key Largo
- La Siesta Resort & Villas
- Manatee Manor ~ 3 Bedroom Island Home on Plantation Key with Pool & Dockage
- Pineapple Beach by Florida Keys Luxury Rentals
- Breathtaking Ocean views! Owners who care. “Sangria Sunrise”! 10% off charters!
- Bayside Villas by Islander Resort
- Boutique Hotels in Islamorada
- Rv Parks in Lignumvitae Key Botanical State Park
- Keys Waterfront Condo
- Oceanfront Hotels in Key Largo
- Hotels near Baker's Cay Resort Beach
- Wynken Blynken and Nod Hotels
- Cottages in Islamorada
- Direct Oceanfront Corner Condo
- Islamorada Hotels
- Marathon Vacations
- Homestead Vacations
- History of Diving Museum
- Visit Key Largo
- Shark Valley Observatory Tower
- Visit Layton
- Visit Seabreeze Trailer Park
- Visit Upper Matecumbe Key
- Baker's Cay Resort Beach
- South Miami Vacations
- Veterans Memorial Park & Beach
- Crane Point Museum and Nature Center
- Visit Islamorada
- Visit Plantation Key
- Islamorada Vacations
- Visit Long Key
- Coral Castle Museum
- Shark Valley Visitor Center
- Sunset Park Beach
- Biscayne National Park
- Zoo Miami
- Sombrero Beach
- Anne's Beach
- Ernest F. Coe Visitor Center
- Florida City Vacations
- Seven Mile Bridge
- Calusa Beach
- Everglades National Park
- Curry Hammock State Park
- Visit Lower Matecumbe Key
- Key Largo Vacations
- Prime Outlets Florida City
- Dagny Johnson Key Largo Hammock Botanical State Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
