Upper Matecumbe Key, FL
Travel Guide
Visit Upper Matecumbe Key
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
The price is NT$6,263 per night from May 21 to May 22
NT$6,263
NT$8,821 total
May 21 - May 22
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! (1,722 reviews)
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Reviewed on 2026/5/15
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is NT$9,432 per night from May 17 to May 18
NT$9,432
NT$12,918 total
May 17 - May 18
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! (1,312 reviews)
I can't say enough good things about the Cheeka Lodge and Spa! The room was beautiful, the staff were amazing, amd the food was spectacular! Highly recommend!
Reviewed on 2026/5/15
Islander Resort
82100 Overseas Highway Islamorada FL
Fully refundable
The price is NT$6,644 per night from May 31 to Jun 1
NT$6,644
NT$9,603 total
May 31 - Jun 1
includes taxes & fees
Book a stay at this 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. ...
9.2/10 Wonderful! (1,014 reviews)
Wonderful time!
Reviewed on 2026/5/16
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! (676 reviews)
Nice, rustic
Reviewed on 2026/5/16
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 ...
9.6/10 Exceptional! (75 reviews)
The "suite" was a single room with a king and pullout sofa, there was no separation. So if you are traveling with children be aware that this is the same as a double queen at any other hotel room.
Reviewed on 2026/4/30
Treasure Harbor
200 Treasure Harbor Dr Islamorada FL
Stay at this houseboat in Islamorada. Enjoy free WiFi, free parking, and premium bedding. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (153 reviews)
This place is absolutely incredible. It offers a perfect harmony with nature—you immediately feel relaxed and at peace as soon as you arrive. The atmosphere is calm, quiet, and truly refreshing, making it the perfect escape from everyday stress. The fishing experience here is amazing. Whether you're ...
Reviewed on 2026/5/3
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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- Eco Pond
- Sunset Drive Beach
- Visit Key Largo
- Visit Key Colony Beach
- Founders Park
- Visit Duck Key
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- Visit Homestead
- Jimmy Johnson's Big Chill
- Visit Big Pine Key
- Flamingo Visitor Center
- Buttonwood Canal
- Anne's Beach
- Visit Pirates Cove
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- Visit Little Venice
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