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


Top hotels in Matecumbe

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is P14,510 per night from Feb 8 to Feb 9
P14,510
per night
Feb 8 - Feb 9
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! (1,662 reviews)
Clean room but cold as it was 42’F in Florida that night and there is no heat in the rooms

Reviewed on Feb 2, 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 P23,426 per night from Feb 7 to Feb 8
P23,426
per night
Feb 7 - Feb 8
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! (1,291 reviews)
Beautiful property, very helpful staff

Reviewed on Feb 1, 2026

Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is P14,688 per night from Feb 8 to Feb 9
P14,688
per night
Feb 8 - Feb 9
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! (1,261 reviews)
Always a favorite! It will be really nice when the tiki bar is finished. That was always a fun spot. The staff is great and love the grounds.

Reviewed on Feb 1, 2026

Amara Cay Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
The price is P22,999 per night from Feb 9 to Feb 10
P22,999
per night
Feb 9 - Feb 10
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! (1,005 reviews)
My husband and I stayed 3 nights and we absolutely loved the resort. Beautiful, quiet and serene and with so many amenities. Our room was amazing with a wonderful huge patio that had a path right out to the beach. Breakfast and dinner at the two restaurants was fabulous with excellent food and great ...

Reviewed on Jan 30, 2026

Islander Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
The price is P18,271 per night from Feb 8 to Feb 9
P18,271
per night
Feb 8 - Feb 9
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 ...
8.6/10 Excellent! (1,000 reviews)
excellent location very nice simple breakfast close to liz’s of activities great poool

Reviewed on Feb 2, 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 P14,479 per night from Feb 8 to Feb 9
P14,479
per night
Feb 8 - Feb 9
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! (1,000 reviews)
The rooms were very clean

Reviewed on Feb 1, 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

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 Windley Key Fossil Reef Geological State Park and Islamorada County 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