Upper Matecumbe Key Travel Guide

Tourist Guide

Upper Matecumbe Key
Upper Matecumbe Key
Upper Matecumbe Key
Upper Matecumbe Key
Upper Matecumbe Key
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is AU$537 per night from 23 June to 24 June
AU$537
23 June - 24 June
includes taxes & fees
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 in their ...
9.2/10 Wonderful! (1,322 reviews)
"All good !!!!!!!!!!!!!!!"

Reviewed on 8 June 2026

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is AU$375 per night from 14 June to 15 June
AU$375
14 June - 15 June
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! (1,747 reviews)
"A beautiful place to stay on the Florida Keys! The staff were all so nice, breakfast was good, and the views were unbeatable. We would definitely consider returning!"

Reviewed on 7 June 2026

Chesapeake Beach Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
The price is AU$530 per night from 23 June to 24 June
AU$530
23 June - 24 June
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the pool and the helpful staff in their reviews. ...
9.4/10 Exceptional! (1,041 reviews)
"Beautiful rooms and resort."

Reviewed on 9 June 2026

Islander Resort
See all 2,763 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! (693 reviews)
"Our stay was great except for the fact we had workers pounding out concrete at 7am in the room right next to us. The rooms are dated but have tasteful updates."

Reviewed on 9 June 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 ...
9.6/10 Exceptional! (76 reviews)
"I am not usually about leaving reviews however this property definitely needs it. Heard a lot about being pampered when I was checked in and that they will bring you anything and to let them know what our needs were. Property does not have any coffee shop or restaurant. We were told we could come ..."

Reviewed on 18 May 2026

The Islands of Islamorada
Treasure Harbor

Treasure Harbor

3 out of 5
200 Treasure Harbor Dr Islamorada FL
Stay at this houseboat 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! (158 reviews)
"We highly recommend Treasure Harbor house boats, it was clean, the A/C was cold, water heater perfect, and close to everything we needed. It’s like a tiny house on water. Dallas, was accommodating and professional. Overall 5+ stars. We visit the keys often for scuba diving, we have now found our ..."

Reviewed on 7 June 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.

Florida Keys Brewing Co.

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

Florida Keys Brewing Co.
Hurricane 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
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

Islamorada Brewery & Distillery

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

Islamorada Brewery & Distillery

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