Matecumbe, FL

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


Matecumbe Hotel Deals

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is ₩360,106 per night from Feb 11 to Feb 12
₩360,106
per night
Feb 11 - Feb 12
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! (1,665 reviews)
We loved this place. It’s small and easy to get around. Beautiful setting, watched the sunrise from bed, and the best hotel breakfast we’ve ever had.

Reviewed on Feb 3, 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 ₩583,956 per night from Feb 10 to Feb 11
₩583,956
per night
Feb 10 - Feb 11
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! (1,294 reviews)
We stayed in Premiere ocean front king. The weather was unusually cold and windy so we didn't get to experience the resort as we had hoped. The staff at restaurants were very courteous and service prompt. Beach is lovely -- although not a natural sand beach. Gym could have been larger. We found spa ...

Reviewed on Feb 4, 2026

Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is ₩486,045 per night from Feb 11 to Feb 12
₩486,045
per night
Feb 11 - Feb 12
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! (1,263 reviews)
All good, nice bartender inside downstairs, and easy walk to fish and eat

Reviewed on Feb 5, 2026

Amara Cay Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
The price is ₩585,420 per night from Feb 10 to Feb 11
₩585,420
per night
Feb 10 - Feb 11
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
Hadley Resort and Marina

Hadley Resort and Marina

3.5 out of 5
82749 Overseas Hwy Islamorada FL
The price is ₩408,330 per night from Feb 10 to Feb 11
₩408,330
per night
Feb 10 - Feb 11
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
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
The price is ₩562,113 per night from Feb 19 to Feb 20
₩562,113
per night
Feb 19 - Feb 20
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
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 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, FL