Upper Matecumbe Key Travel Guide

Tourist Guide

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

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is 4.977.876 ₫ per night from 6 Jan to 7 Jan
4.977.876 ₫
7.081.196 ₫ total
6 Jan - 7 Jan 2026
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! (1,602 reviews)
It was a great breakfast.... they had everything that i liked in particular. They had healthy options.. not a big place so it didnt seem overwhelmed with options just the right amount of options. Place i staid had an amazing ocean view :)

Reviewed on 23 Dec 2025

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is 6.202.925 ₫ per night from 4 Jan to 5 Jan
6.202.925 ₫
8.726.143 ₫ total
4 Jan - 5 Jan 2026
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! (1,265 reviews)
Clean rooms! Great resort , fun activities , very nice and quiet area , made my anniversary with my girlfriend very special!

Reviewed on 21 Dec 2025

Amara Cay Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is 7.872.969 ₫ per night from 4 Jan to 5 Jan
7.872.969 ₫
10.782.808 ₫ total
4 Jan - 5 Jan 2026
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! (1,276 reviews)
AMAZING.

Reviewed on 21 Dec 2025

Cheeca Lodge & Spa
See all 2,815 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! (588 reviews)
Spotless room- right on beach- really enjoyed

Reviewed on 17 Dec 2025

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! (69 reviews)
Beautiful accommodations and location, very clean, many activities available at resort

Reviewed on 25 Nov 2025

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 ...
8.8/10 Excellent! (117 reviews)
I am obsessed with tiny houses and this one floats! It was so relaxing to sit on the deck and enjoy the view. The bed was very comfy and the gentle motion of the water put me right to sleep. The staff are friendly and helpful. Islamorada is beautiful and fun to explore.

Reviewed on 25 Nov 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

You can spend an afternoon browsing the exhibits at History of Diving Museum during your travels in Islamorada. Amble around this family-friendly area's seaside and enjoy its lively bars.

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

Hurricane Monument

Learn about the local history of Islamorada when you take a trip to Hurricane Monument. Discover the beautiful sunsets and lively bars in this family-friendly area.

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

Keys History & Discovery Center

You can spend time studying the exhibits at Keys History & Discovery Center during your trip to Islamorada.

Keys History & Discovery Center