Matecumbe Travel Guide

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


Top hotels in Matecumbe

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is ฿6,205 per night from 2 Feb to 3 Feb
฿6,205
per night
2 Feb - 3 Feb
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! (1,655 reviews)
Staff was very nice. Nice to use the complimentary clear bottom kayaks. Breakfast was good, Didi made a great omelette!

Reviewed on 24 Jan 2026

Chesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is ฿9,344 per night from 1 Feb to 2 Feb
฿9,344
per night
1 Feb - 2 Feb
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! (1,301 reviews)
This palce is awesome. Clean rooms. 2 large pools with a view. Covered garage spot.

Reviewed on 22 Jan 2026

Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is ฿7,784 per night from 2 Feb to 3 Feb
฿7,784
per night
2 Feb - 3 Feb
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! (1,276 reviews)
We enjoyed our stay and found the staff to be courteous and responsive. Our room was a generous size, clean and well appointed (as is often the case we wouldn’t have said no to a couple of more outlets lol). The beach and pool areas had plenty of seating and multiple things to do—ping pong, cornhole, ...

Reviewed on 26 Jan 2026

Amara Cay Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
The price is ฿10,735 per night from 2 Feb to 3 Feb
฿10,735
per night
2 Feb - 3 Feb
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! (1,000 reviews)
This place is great. A must stay. Everyone is so friendly. Place is spotless clean

Reviewed on 22 Jan 2026

Islander Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
The price is ฿6,940 per night from 2 Feb to 3 Feb
฿6,940
per night
2 Feb - 3 Feb
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 ...
8.6/10 Excellent! (1,000 reviews)
We stayed in one of the bungalows and absolutely loved it! It was awesome to walk right out of your room onto the beach. We really enjoyed the kayaking.

Reviewed on 23 Jan 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 ฿6,848 per night from 2 Feb to 3 Feb
฿6,848
per night
2 Feb - 3 Feb
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! (1,003 reviews)
Friendly staff and they did have breakfast. Room was right on the water beautiful view

Reviewed on 22 Jan 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.

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 Windley Key Fossil Reef Geological State Park and Islamorada County 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 Travel Guide