Matecumbe, FL

Islamorada

Islamorada showing a beach bar
Islamorada showing a sandy beach
Islamorada
Islamorada featuring mangroves, general coastal views and a marina
Islamorada which includes a sandy beach, general coastal views and tropical scenes

Popular places to visit

Anne\'s Beach featuring a bridge

Anne's Beach

If a restful vacation is part of your travel plans, Anne's Beach might be the perfect place to seek out during your trip to Islamorada.

Anne's Beach
Florida Keys Brewing Co. showing signage

Florida Keys Brewing Co.

You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.

Florida Keys Brewing Co.
History of Diving Museum showing heritage elements

History of Diving Museum

Trace one of the world’s most astonishing watersports back through the centuries to see some of the first diving suits as you explore this interactive museum, featuring the world's largest international collection of diving artifacts.

History of Diving Museum
Hurricane Monument which includes a monument and outdoor art

Hurricane Monument

The memories of those lost to the 1935 Labor Day Hurricane live on at this moving tribute and burial site along the Overseas Highway.

Hurricane Monument

Bud n' Mary's Dive Center

Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this family-friendly area.

Bud n' Mary's Dive Center

Robbie’s of Islamorada

Explore the waterfront in Islamorada with a trip to Robbie’s of Islamorada.

Robbie’s of Islamorada

Matecumbe Hotel Deals

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
The price is ₩210,189 per night from Aug 17 to Aug 18
₩210,189
₩314,734 total
Aug 17 - Aug 18
includes taxes & fees
Stay at this 3.5-star beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
9/10 Wonderful! (1,487 reviews)
"The Chesapeake Beach Resort was lovely. It is a small, clean, picturesque resort. We had the beautiful beach area with pool towels and lounge chairs to ourselves. We were surprised and excited about the 2 free hours of either paddle boarding, kayaking, or fishing poles per day. The free breakfast ..."

Reviewed on Aug 7, 2025

Chesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
The price is ₩221,252 per night from Aug 14 to Aug 15
₩221,252
₩342,836 total
Aug 14 - Aug 15
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 ...
9/10 Wonderful! (1,141 reviews)
"Great all around!"

Reviewed on Aug 8, 2025

Cheeca Lodge & Spa
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
The price is ₩289,436 per night from Aug 20 to Aug 21
₩289,436
₩419,543 total
Aug 20 - Aug 21
includes taxes & fees
Stay at this 4-star 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. ...
9/10 Wonderful! (1,009 reviews)
"We enjoyed staying at Islander Resort. Our pool bungalow room was very clean and in a great location to the pool & ocean."

Reviewed on Aug 9, 2025

Islander Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
The price is ₩233,879 per night from Sep 1 to Sep 2
₩233,879
₩355,483 total
Sep 1 - Sep 2
includes taxes & fees
Stay at this 4-star beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the bar in our reviews. ...
8.8/10 Excellent! (1,237 reviews)
Perfect Resort
"Great time with friends at Amara Cay Resort. We stayed in the one bedroom with 2 queen beds which was the perfect set up for us with a little kitchen and sitting area. The water taxi to the other resorts was an added bonus."

Reviewed on Aug 9, 2025

Amara Cay Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway, Islamorada, FL
The price is ₩205,701 per night from Sep 1 to Sep 2
₩205,701
₩323,783 total
Sep 1 - Sep 2
includes taxes & fees
Stay at this 4-star 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! (1,004 reviews)
"My family had a great stay at La Siesta Resort! The staff was very kind and welcoming; they had everything ready ahead of our stay and even provided us with a free upgrade on the accommodation to boot! The pool and beach/marina area are great spaces and there were beach chairs and umbrellas throughout. ..."

Reviewed on Aug 10, 2025

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 ₩155,293 per night from Aug 17 to Aug 18
₩155,293
₩220,109 total
Aug 17 - Aug 18
includes taxes & fees
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! (1,006 reviews)
Gem in Islamorada
"I love this place, it’s chill, dog friendly, ramp and docks for ease of throwing in my paddleboard. Insanely beautiful views, and central to everything."

Reviewed on Jul 17, 2025

Hadley Resort and Marina
See all 580 properties in Matecumbe
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

Delicious fried conch & the YUMMIEST Cuban food in town :D

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
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Venetian Shores

Venetian Shores might not have many top sights, but Islamorada County Park and Founders Park are two attractions nearby that you can check out.

Venetian Shores
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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 Founders Park and Islamorada County Park.

Seabreeze Trailer Park

Matecumbe, FL