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!


Top hotels in Matecumbe

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is S$656 per night from 24 Feb to 25 Feb
S$656
24 Feb - 25 Feb
includes taxes & fees
Stay at this 5-star 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! (1,309 reviews)
It was sublime.....bungalow on the beach was perfect. The only thing was no room service came to clean up...trays were left outside the doors for the whole time we were there. So odd. But everything else was perfect. I love the Cheeca Lodg

Reviewed on 21 Feb, 2026

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is S$514 per night from 1 Mar to 2 Mar
S$514
1 Mar - 2 Mar
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...
9.2/10 Wonderful! (1,670 reviews)
Great vibe….very clean rooms. Wahoo next door is also fun and good food.

Reviewed on 23 Feb, 2026

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is S$490 per night from 8 Mar to 9 Mar
S$490
8 Mar - 9 Mar
includes taxes & fees
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 their reviews. ...
8.8/10 Excellent! (1,265 reviews)
Room had a musty odor. Tiki bar staff non attentive. Grounds were beautiful

Reviewed on 22 Feb, 2026

Amara Cay Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
The price is S$434 per night from 1 Mar to 2 Mar
S$434
1 Mar - 2 Mar
includes taxes & fees
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 rooms ...
8.8/10 Excellent! (1,004 reviews)
Our favorite part was the Rum Runner boat taxi. Captain Jen and Mate Bruce weee wonderful.

Reviewed on 21 Feb, 2026

La Siesta Resort & Villas
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
The price is S$558 per night from 24 Mar to 25 Mar
S$558
24 Mar - 25 Mar
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the pool and the helpful staff in their reviews. ...
9.2/10 Wonderful! (1,009 reviews)
Great resort, easy check in and courteous staff. Nice pools and grounds.

Reviewed on 22 Feb, 2026

Islander Resort
Hadley Resort and Marina

Hadley Resort and Marina

3.5 out of 5
82749 Overseas Hwy Islamorada FL
The price is S$438 per night from 3 Mar to 4 Mar
S$438
3 Mar - 4 Mar
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular attractions ...
7.6/10 Good! (1,002 reviews)
All of the above!! When I receive my refund for a cancelled one night, I will give a further review.

Reviewed on 22 Feb, 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 Holiday Sale

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Other neighbourhoods around Matecumbe

Anne’s beach is on Lower Matecumbe Key

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.

Lower Matecumbe Beach
Colorful Island Palm Tree Sunset

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 Windley Key Fossil Reef Geological State Park.

Venetian Shores
Coastline of Islamorada, panoramic view at dusk

Seabreeze Trailer Park

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

Seabreeze Trailer Park


Matecumbe