Matecumbe Holidays

Photo by Shannon Rocco

  • 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

Where to stay in Matecumbe

Find the best Matecumbe areas and neighborhoods for the activities you enjoy most. Learn more about Matecumbe
A sunset over a palm tree-lined pier extending into calm waters.

Venetian Shores

Though Venetian Shores may not have many top sights, you can venture to the surrounding area to see attractions like Islamorada County Park and Founders Park.

Find hotels in Venetian Shores
A clear blue sea with a sandy beach and a distant horizon.

Lower Matecumbe Beach

While Lower Matecumbe Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Anne's Beach and Sunset Drive Beach.

Find hotels in Lower Matecumbe Beach
A beach with palm trees, lounge chairs, and a building with balconies.

Seabreeze Trailer Park

While there might not be top attractions in Seabreeze Trailer Park, you can explore the larger area and discover places like Founders Park and Islamorada County Park.

Find hotels in Seabreeze Trailer Park

Top hotels in Matecumbe

Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
S$308
18 Aug - 19 Aug
includes taxes & fees
Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
S$282
15 Sept - 16 Sept
includes taxes & fees
9.2/10 Wonderful! (1,745 reviews)
"Very nice staff. Room was clean. Property had some nice things but the pool was not clean at all and the jacuzzi did not work."

Reviewed on 14 Aug, 2026

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
S$326
15 Sept - 16 Sept
includes taxes & fees
8.8/10 Excellent! (1,281 reviews)
"Always a good time!"

Reviewed on 14 Aug, 2026

Amara Cay Resort
See all 559 properties in Matecumbe
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 Matecumbe attractions

A sandy beach with green vegetation and a calm sea.

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
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 family-friendly area.
See properties
A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

Florida Keys Brewing Co.

9.2/10 (520 reviews)
You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.
See properties
A building with a blue facade, a large mural of a diving scene, and a statue of a diver.

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.
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

Islamorada Brewery & Distillery

9.4/10 (8 reviews)
You can take time to visit Islamorada Brewery & Distillery during your travels to 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

Keys History & Discovery Center

You can spend time studying the exhibits at Keys History & Discovery Center during your trip to Islamorada.
See properties

* 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.