Upper Matecumbe Key

Travel Guide

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

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is P11,575 per night from Aug 14 to Aug 15
P11,575
P16,948 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! (1,138 reviews)
"So this is my first time visiting Cheeca Lodge- I have alway"

Reviewed on Jul 28, 2025

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
The price is P8,786 per night from Aug 12 to Aug 13
P8,786
P13,156 total
Aug 12 - Aug 13
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! (1,480 reviews)
"I stayed here a long time ago prior to the renovations and I was please to find that it’s still the same great place just a lot nicer."

Reviewed on Aug 1, 2025

Chesapeake Beach Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
The price is P12,098 per night from Aug 12 to Aug 13
P12,098
P17,536 total
Aug 12 - Aug 13
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! (1,003 reviews)
"This place was amazing! It definitely had a resort feel and was very clean. Even though the beaches aren't the normal tropic island beaches everthing inside the resort made you feel you were on an island. The staff was very helpful and friendly. The parking was free and right outside our room. The ..."

Reviewed on Aug 1, 2025

Islander Resort
See all 2,747 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
Book a stay at this beach aparthotel in Islamorada. Enjoy free WiFi, a beach locale, and a marina. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (497 reviews)
"Owner/manager was terrific. Walls are thin- could hear neighbor snoring Bummer that smoking was allowed on and near the jetty. Pool.was busy and family oriented but pleasant and clean. Cool vanity in bathroom- albeit there seemed to be a former medical stand being used as furniture in living room. ..."

Reviewed on Jul 28, 2025

Breezy Palms Resort
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy, Islamorada, FL
Stay at this 4-star beach villa in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada ...
9.6/10 Exceptional! (65 reviews)
"Amazing stay, can’t wait to stay there again!"

Reviewed on Jul 25, 2025

The Islands of Islamorada
Treasure Harbor

Treasure Harbor

3 out of 5
200 Treasure Harbor Dr, Islamorada, FL
Stay at this 3-star hotel in Islamorada. Enjoy free WiFi, free parking, and premium bedding. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (91 reviews)
"Unique House boat experience, friendly staff."

Reviewed on Jul 29, 2025

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

Florida Keys Brewing Co.

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

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 featuring 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

Islamorada Brewery & Distillery

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

Islamorada Brewery & Distillery

Matecumbe United Methodist Church

Find out about the history of Islamorada with a stop at Matecumbe United Methodist Church. Discover the beautiful sunsets in this family-friendly area, or enjoy its fishing spots.

Matecumbe United Methodist Church