Lower Matecumbe Key Holidays

  • 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

Top hotels in Lower Matecumbe Key

Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay

73801 Overseas Hwy Islamorada FL
Get rates
Caloosa Cove Resort by CoolVacay
Matecumbe Resort

Matecumbe Resort

76261 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
S$183
20 Sept - 21 Sept
includes taxes & fees
9/10 Wonderful! (162 reviews)
"Great place! Had the room with ocean view and it was fantastic! Perfect little place to stay"

Reviewed on 12 Sept, 2026

Matecumbe Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
S$305
15 Sept - 16 Sept
includes taxes & fees
Cheeca Lodge & Spa
See all 2,078 properties in Lower 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 Lower Matecumbe Key attractions

Anne's Beach

7.8/10 (597 reviews)
If a restful holiday is part of your travel plans, Anne's Beach might be the perfect place to visit during your trip to Islamorada.
See properties

Robbie’s of Islamorada

8.4/10 (15 reviews)
Explore the waterfront in Islamorada with a trip to Robbie’s of Islamorada.
See properties

Sunset Drive Beach

9.0/10 (91 reviews)
Why not spend a lazy afternoon at Sunset Drive Beach during your trip to Islamorada?
See properties

Frequently asked questions

How much does a Lower Matecumbe Key holiday package cost?
Custom build your Lower Matecumbe Key holiday package from an affordable . Choose from any combination of flights, hotels and rental cars to put together the escape you've long been dreaming about. Be sure to add on a few experiences or tours!
How do I get a cheap travel package to Lower Matecumbe Key?
You'll save big if you combine your hotels, car rentals and flights into a Lower Matecumbe Key travel package. Sometimes cheap means fewer options. But that's not the case with Expedia. We offer more than 550 partner airlines and 1,000,000 hotels worldwide, so you'll always have plenty of variety to choose from. Want to save even more? Add some exciting activities to your package deal to unlock even more bargains! After all, travel is about more than just getting to your destination.
How far in advance should I book my Lower Matecumbe Key holiday?
Reward yourself with the biggest variety at the cheapest prices by booking your trip to Lower Matecumbe Key early. Airlines typically sell flight tickets around a year before departure, so secure your spot as soon as possible. Having said that, Expedia is committed to giving you the best deals around, so there's never a bad time to book your dream holiday!
What does an Expedia Lower Matecumbe Key travel package include?
Flights, hotels and a shiny set of wheels for your road trip adventures. Simply pick and choose your preferred bundle and get access to incredible deals. Once you've made your booking, add on a couple of tours and experiences and watch your savings grow. When it comes to crafting your Lower Matecumbe Key getaway, you're the one in control!
What should I know before booking a Lower Matecumbe Key travel package?
You'll save big with an Expedia travel package. Bundle your flights, rental cars and hotels and enjoy fantastic discounts. You're not restricted to hotels, though. We have island resorts, cabins in the mountains and even treehouses and ranches!
Can I choose my airline with a Lower Matecumbe Key Expedia holiday package?
With a holiday package, you're the boss. Whether you're hoping to fly to Lower Matecumbe Key in economy or business class, simply choose from the available airline options. Expedia has access to more than 550 airline partners globally.
If I'm not able to travel, can I cancel my Lower Matecumbe Key holiday package?
Certainly, and we're here to help. You may be able to cancel or change your Lower Matecumbe Key holiday package at no cost if you booked in the last 24 hours. But you may incur a fee from your hotel, airline or car rental company for older bookings. If your travel plans suddenly 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.