Upper Matecumbe Key Holidays

Photo by Cameron Abbott

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 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

Upper Matecumbe Key Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Cordova Arms on the River by Rocketstay

Cordova Arms on the River by Rocketstay

3 out of 5
East Fort Lauderdale
Save 100% on your flight
Price was S$1,958, price is now S$1,318 per person
S$1,318
per person
22 Dec - 28 Dec
found 1 day ago
Return direct flight included
Philipsburg (SXM) to Miami (MIA)
9.4/10 Exceptional! (222 reviews)
Wow wow wow. The place was so clean. Immaculate actually. The property was so quiet and well kept. Felt so comfortable in comparison to other places I’ve stayed. I will definitely use this place everytime I’m back in Fort Lauderdale. This definitely is my go to spot now. The pool was nice and it’s right on the water in a great spot close to local restaurants and everything. And communication with the property manager was easy and so accommodating

Reviewed on 28 Oct, 2026

Artrageous on the river By RocketStay

Artrageous on the river By RocketStay

3.5 out of 5
East Fort Lauderdale
Save 100% on your flight
Price was S$2,844, price is now S$1,660 per person
S$1,660
per person
23 Dec - 28 Dec
found 1 day ago
Return direct flight included
Philipsburg (SXM) to Miami (MIA)
8.2/10 Very good! (354 reviews)
The apartment is nice and very well located, and the host was very friendly. However, we had no Wi-Fi throughout our stay, there was no hot water in the shower, and the parking spot assigned to us was occupied by another car when we arrived at night, which caused us some inconvenience.

Reviewed on 12 Oct, 2026

Mahalo Isles Apartments by Rocketstay

Mahalo Isles Apartments by Rocketstay

3 out of 5
East Fort Lauderdale
Save 100% on your flight
Price was S$2,831, price is now S$1,787 per person
S$1,787
per person
22 Dec - 28 Dec
found 1 day ago
Return direct flight included
Philipsburg (SXM) to Miami (MIA)
10/10 Exceptional! (6 reviews)
Love it

Reviewed on 21 Sept, 2026

The Sunny Miami Sunny Isles Beach,Curio Collection by Hilton

The Sunny Miami Sunny Isles Beach,Curio Collection by Hilton

4 out of 5
Ocean Four
Save 100% on your flight
Price was S$2,860, price is now S$1,897 per person
S$1,897
per person
22 Dec - 28 Dec
found 1 day ago
Return direct flight included
Philipsburg (SXM) to Miami (MIA)
9/10 Wonderful! (874 reviews)

The Atlantic Hotel & Spa

The Atlantic Hotel & Spa

4.5 out of 5
East Fort Lauderdale
Save 100% on your flight
Price was S$2,582, price is now S$1,763 per person
S$1,763
per person
22 Dec - 28 Dec
found 1 day ago
Return direct flight included
Philipsburg (SXM) to Miami (MIA)
9/10 Wonderful! (1,978 reviews)

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 S$324 per night from 1 Nov to 2 Nov
S$324
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 S$276 per night from 3 Nov to 4 Nov
S$276
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 S$321 per night from 15 Nov to 16 Nov
S$321
15 Nov - 16 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.

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 holiday package cost?
Starting from a low S$1,318, 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 holiday 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 holiday?
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 holiday package?
Yes — that's one of the best things about an Expedia holiday 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 holiday 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 holiday 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

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.