Upper Matecumbe Key
Travel Guide
Visit Upper Matecumbe Key
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is CA $373 per night from May 3 to May 4
CA $373
CA $519 total
May 3 - May 4
includes taxes & fees
Book a 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 ...
9.2/10 Wonderful! (1,315 reviews)
Booked premium beachfront king suite 40 days in advance. Confirmed the day before and when we got there we were given a double queen bed suite. Disappointed
Reviewed on Apr 16, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
The price is CA $247 per night from May 10 to May 11
CA $247
CA $355 total
May 10 - May 11
includes taxes & fees
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (1,688 reviews)
The staff was competent. The patrons were pleasant. The rooms were always clean magically around the day. They did a really good job restocking the towels It was nice to have a different towel each day. we struggled a bit with the fishing poles, because the lines were always really tangled but having ...
Reviewed on Apr 17, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
The price is CA $386 per night from May 17 to May 18
CA $386
CA $534 total
May 17 - May 18
includes taxes & fees
Book a 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 ...
8.8/10 Excellent! (1,264 reviews)
No clean room every day
Reviewed on Apr 16, 2026
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
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 ...
8.8/10 Excellent! (660 reviews)
Newly refurbished, beautifully set up with full kitchen, living and large shower all brand new last year. Fantastic value and will be back for sure with family this summer. Check in super easy, fabulous location, walk to Bud and Mary’s, Lorelei and Bass pro and Islamorada Fush Company all less than ...
Reviewed on Apr 17, 2026
The Islands of Islamorada
82779 Old Hwy Islamorada FL
Book a stay at this beach villa in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada ...
9.8/10 Exceptional! (74 reviews)
What a wonderful venue for our last 2 nights in the Keys. This place is a hidden gem. The entire staff, especially Edith, the bartender, were fantastic.
Reviewed on Apr 14, 2026
Oceanfront Private Cottage!
Islamorada FL
Stay at this cottage in Islamorada. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions History of Diving Museum and Islamorada Brewery ...
10/10 Exceptional! (114 reviews)
My husband and I really enjoyed our stay. The cottage was very clean and had all the amenities we needed for the perfect week! We were so thankful the owner provided a bunch of bumpers due to the heavy winds in order for our boat to be protected. The location of the cottage was perfect. We were able ...
Reviewed on Apr 15, 2026
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
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.
Florida Keys Brewing Co.
You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.
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.
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.
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.
Islamorada Brewery & Distillery
You can take time to visit Islamorada Brewery & Distillery during your travels to Islamorada.
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- Visit Bahia Honda Key
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- Visit Big Pine Key
- Visit Duck Key
- Visit Florida City
- Visit Grassy Key
- Visit Homestead
- Hurricane Monument
- Visit Lower Matecumbe Beach
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- Visit Seabreeze Trailer Park
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- Visit Islamorada
- Visit Anglers Park
- Visit Buccaneer Point
- Visit Largo Sound Village
- Visit Wynken Blynken and Nod
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- Visit Layton
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- Visit Little Torch Key
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- Visit Marathon
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