Upper Matecumbe Key Travel Guide

Tourist Guide

Islamorada Florida. Beautiful Beach and Amazing Fishing. What else can you ask for.
Islamorada Florida. Beautiful Beach and Amazing Fishing. What else can you ask for.
Cheeca Pier 🎣 🛶
Pelican posing for the camera in Islamorada, Florida, in the Florida Keys.
Islamorada in the Florida Keys
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is ฿9,113 per night from 3 Mar to 4 Mar
฿9,113
฿11,999 total
3 Mar - 4 Mar
includes taxes & fees
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! (1,661 reviews)
warm pool, beautiful view at the beach, pleasant front desk and breakfast staff

Reviewed on 28 Feb 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 ฿16,733 per night from 2 Mar to 3 Mar
฿16,733
฿21,095 total
2 Mar - 3 Mar
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 ...
9.2/10 Wonderful! (1,298 reviews)
This Resort is unbelievable from the rooms to the beach, walking & biking trails, golf course 27 acres of lush property. Lots of shops & restaurants nearby including Bass Pro Shop, small artists shops & brewery within walking/biking distance.

Reviewed on 25 Feb 2026

Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ฿9,619 per night from 8 Mar to 9 Mar
฿9,619
฿13,091 total
8 Mar - 9 Mar
includes taxes & fees
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! (1,255 reviews)
Loved the outdoor spaces! Sunrise was beautiful! Room was nice. Great staff!

Reviewed on 28 Feb 2026

Amara Cay Resort
See all 2,793 properties in Upper Matecumbe Key
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.
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway Islamorada FL
Stay at this beach aparthotel in Islamorada. Enjoy free Wi-Fi, a beach locale and a marina. Our guests praise the helpful staff and the clean rooms in their ...
8.8/10 Excellent! (624 reviews)
location was excellent, room was awesome, grounds were the best

Reviewed on 27 Feb 2026

Breezy Palms Resort
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy Islamorada FL
Stay at this beach villa in Islamorada. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada Brewery ...
9.8/10 Exceptional! (71 reviews)
This place exceeded my expectations. Such a beautiful and quiet setting. Don't want to leave, but I will definitely be backa a beautiful

Reviewed on 27 Feb 2026

The Islands of Islamorada
Treasure Harbor

Treasure Harbor

3 out of 5
200 Treasure Harbor Dr Islamorada FL
Stay at this hotel in Islamorada. Enjoy free Wi-Fi, free parking and premium bedding. Our guests praise the helpful staff in their reviews. Popular attractions ...
9/10 Wonderful! (136 reviews)
Clean and tidy. Great location

Reviewed on 27 Feb 2026

Treasure Harbor
See all properties in Upper Matecumbe Key
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.

Popular places to visit

Islamorada_BudnMarysDiveCenter_6069243-0004

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
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 outdoor art and a monument

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
Islamorada_MatecumbeUnitedMethodistChurch_553248621532652347-0004

Matecumbe United Methodist Church

After visiting Matecumbe United Methodist Church, make a plan to see the other sights and activities in Islamorada. Discover the beautiful sunsets in this family-friendly area or enjoy its fishing spots.

Matecumbe United Methodist Church

Islamorada Brewery & Distillery

You can take time to visit Islamorada Brewery & Distillery during your travels to Islamorada.

Islamorada Brewery & Distillery

Cities near Upper Matecumbe Key

Islamorada showing a beach and tropical scenes

Islamorada