Matecumbe

Islamorada

Cheeca Pier 🎣 🛶
Cheeca Pier 🎣 🛶
Pelican posing for the camera in Islamorada, Florida, in the Florida Keys.
Islamorada in the Florida Keys
Sunset in the Florida Keys while an egret looks for a snack!

Popular places to visit

Things to do


Matecumbe Hotel Deals

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is CA $691 per night from Mar 1 to Mar 2
CA $691
CA $878 total
Mar 1 - Mar 2
includes taxes & fees
Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
9.2/10 Wonderful! (1,298 reviews)
This Resort is unbelievable from the rooms to the beach, walking & biking trails, golf course 27 acres of lush property. Lots of shops & restaurants nearby including Bass Pro Shop, small artists shops & brewery within walking/biking distance.

Reviewed on Feb 25, 2026

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 CA $397 per night from Mar 3 to Mar 4
CA $397
CA $524 total
Mar 3 - Mar 4
includes taxes & fees
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (1,658 reviews)
Very comfortable with nice rooms. Attentive on site management.

Reviewed on Feb 27, 2026

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is CA $403 per night from Mar 8 to Mar 9
CA $403
CA $554 total
Mar 8 - Mar 9
includes taxes & fees
Book a stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the helpful staff in ...
8.8/10 Excellent! (1,254 reviews)
Staff excellent. Clean room and surroundings

Reviewed on Feb 27, 2026

Amara Cay Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
The price is CA $581 per night from Mar 4 to Mar 5
CA $581
CA $746 total
Mar 4 - Mar 5
includes taxes & fees
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,004 reviews)
Our king room was spacious and clean with a very comfortable bed and nice linens. Very well maintained grounds and a nice bar by the pool with a great view of the ocean. I would definitely recommend!

Reviewed on Feb 27, 2026

Islander Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
The price is CA $356 per night from Mar 4 to Mar 5
CA $356
CA $501 total
Mar 4 - Mar 5
includes taxes & fees
Book a stay at this beach resort in Islamorada. Enjoy a private beach, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the spacious ...
8.8/10 Excellent! (1,000 reviews)
Our favorite part was the Rum Runner boat taxi. Captain Jen and Mate Bruce weee wonderful.

Reviewed on Feb 21, 2026

La Siesta Resort & Villas
Hadley Resort and Marina

Hadley Resort and Marina

3.5 out of 5
82749 Overseas Hwy Islamorada FL
The price is CA $324 per night from Mar 1 to Mar 2
CA $324
CA $409 total
Mar 1 - Mar 2
includes taxes & fees
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
7.6/10 Good! (1,002 reviews)
Great location in Islamorada. The local beach is non existent (dock station really), but there are very good dining and swimming options within 10 minutes of driving Friendly staff, great breakfast and great breakfast setting outside

Reviewed on Feb 27, 2026

Hadley Resort and Marina
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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

Other neighbourhoods around Matecumbe

Anne’s beach is on Lower Matecumbe Key

Lower Matecumbe Beach

Though Lower Matecumbe Beach might not have many top sights, you can venture to the surrounding area to see attractions like Anne's Beach and Sunset Drive Beach.

Lower Matecumbe Beach
Colorful Island Palm Tree Sunset

Venetian Shores

Venetian Shores might not have many top sights, but Islamorada County Park and Windley Key Fossil Reef Geological State Park are two attractions nearby that you can check out.

Venetian Shores
Coastline of Islamorada, panoramic view at dusk

Seabreeze Trailer Park

If you're looking for some top things to see and do in Seabreeze Trailer Park and surrounding area, you can visit Islamorada County Park and Founders Park.

Seabreeze Trailer Park


Matecumbe

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