Matecumbe, FL

Islamorada

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!
Worlds best tarpon fishing marina!! They grow 8 feet and are scary looking, feed them rite from the Dock!

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 ¥47,121 per night from Apr 12 to Apr 13
¥47,121
per night
Apr 12 - Apr 13
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)
We did not use the spa services, we may have been able to barely see a small portion of the ocean out a window

Reviewed on Mar 12, 2026

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is ¥34,586 per night from Apr 14 to Apr 15
¥34,586
per night
Apr 14 - Apr 15
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! (1,666 reviews)
We upgraded to an Ocean View and it was fantastic! Nice quiet vacation and great location with walkable restaurants and bars. Breakfast was special with awesome omlets by Chris!!

Reviewed on Mar 13, 2026

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is ¥37,327 per night from Mar 23 to Mar 24
¥37,327
per night
Mar 23 - Mar 24
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! (1,252 reviews)
We had a partial view of ocean from our room. We did not use the pool but it was a decent looking. The staff was kind and professional. The room we had smelled of mold strongly.

Reviewed on Mar 12, 2026

Amara Cay Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
The price is ¥55,721 per night from Apr 12 to Apr 13
¥55,721
per night
Apr 12 - Apr 13
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)
We had a beautiful time during our stay. The rooms are so comfortable and have beautiful views. The staff was kind and even checked on us to see if we needed more coffee. The views were perfect day and night. We enjoyed the pool and played some golf and relaxed. Best week ever!

Reviewed on Mar 14, 2026

Islander Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
The price is ¥35,230 per night from Mar 23 to Mar 24
¥35,230
per night
Mar 23 - Mar 24
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)
Great place

Reviewed on Mar 6, 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 ¥44,472 per night from Mar 19 to Mar 20
¥44,472
per night
Mar 19 - Mar 20
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! (1,003 reviews)
We were suppose to have pool villa. No view of the pool from our room. Did get $100 off our stay. Pool was dirty. Continental breakfast was good. Need railings in room for stairs. Need table lamp in living room. Shared balcony. Was woken up by loud music on balcony at 11 pm one night.

Reviewed on Mar 13, 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 neighborhoods 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, FL