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
The price is P23,344 per night from 2 Feb to 3 Feb
P23,344
P30,212 total
includes taxes & fees
Feb 2 - Feb 3
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! (1,023 reviews)
"Stunning views and property, comfy and quiet rooms.Excellent service especially the tiki bar!"

Reviewed on Jan 20, 2025

Cheeca Lodge & Spa
Chesapeake Beach Resort
Chesapeake Beach Resort
2.5 out of 5
83409 Overseas Hwy, Islamorada, FL
The price is P15,147 per night from 26 Jan to 27 Jan
P15,147
P19,965 total
includes taxes & fees
Jan 26 - Jan 27
Book a stay at this beach hotel in Islamorada. Enjoy 2 outdoor pools, a private beach, and a 24-hour front desk. Our guests praise the breakfast and the pool ...
9/10 Wonderful! (1,394 reviews)
"Lovely beach resort in Islamorada Two large pools, location is great with its own little private beach"

Reviewed on Jan 20, 2025

Chesapeake Beach Resort
Amara Cay Resort
Amara Cay Resort
4 out of 5
80001 Overseas Hwy, Islamorada, FL
The price is P16,947 per night from 11 Feb to 12 Feb
P16,947
P22,950 total
includes taxes & fees
Feb 11 - Feb 12
Stay at this 4-star beach resort in Islamorada. Enjoy free parking, 2 restaurants, and a private beach. Our guests praise the pool and the bar in our reviews. ...
8.8/10 Excellent! (1,208 reviews)
"Beautiful beach and fun beach games"

Reviewed on Jan 21, 2025

Amara Cay Resort
See all 2,767 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 ...
8.4/10 Very Good! (398 reviews)
"This is a great little place to stay at a very good rate. It is walking distance to some amazing restaurants. The room had been updated, it was clean. Staff was friendly but I wouldn’t say they go out of their way. The beach is good for relaxing at but it’s pretty shallow a long way out so not much ..."

Reviewed on Jan 16, 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! (44 reviews)
"This property was immaculate, a great blend of an upscale hotel feel with a vacation rental. We loved all the amenities. Would highly recommend!"

Reviewed on Jan 14, 2025

The Islands of Islamorada
Mangrove Marina and Resort Aqualodge Houseboats
Mangrove Marina and Resort Aqualodge Houseboats
3 out of 5
200 Florida Ave, Tavernier, FL
Stay at this 3-star houseboat in Tavernier. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.2/10 Wonderful! (326 reviews)
"Gorgeous view, generally quiet. Location just a short drive from numerous dining locations. Would stay again!"

Reviewed on Nov 22, 2024

Mangrove Marina and Resort Aqualodge Houseboats
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