Name: Islander Resort
Price range: ₹19,882
Rating: 9.2

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

₹16,271

₹23,603 total

10 May - 11 May

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! (1,709 reviews)

Breakfast area too small. Was chilly for Florida - no seating indoor or outdoor to eat your breakfast.

Reviewed on 27 Apr 2026

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

₹23,939

₹33,820 total

3 May - 4 May

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! (1,317 reviews)

We had an ocean front room in the new wing and can honestly say it was lovely. The staff were great, the hotel facilities were lovely and food and drinks all good.

Reviewed on 28 Apr 2026

Islander Resort

82100 Overseas Highway Islamorada FL

₹19,882

₹28,725 total

17 May - 18 May

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. ...

9.2/10 Wonderful! (1,008 reviews)

Mire options ( restaurant)

Reviewed on 26 Apr 2026

See all 2,810 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

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! (666 reviews)

Room was very clean and the bed was fantastically comfortable! Furniture was a bit out dated and not as comfortable as I would have liked. Pool was fantastic as well!

Reviewed on 26 Apr 2026

The Islands of Islamorada

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 ...

9.8/10 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 14 Apr 2026

Treasure Harbor

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! (150 reviews)

Place was as described. Only thing i would recommend is a little more attention to detail during turnover cleaning as we found nail clippings and foot splatter on the wall. We loved the setting after our long days being able to be on the water, had manatees swim by us a couple times. Still recommend ...

Reviewed on 16 Apr 2026

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.

Stay near popular South Florida attractions

Bud n' Mary's Dive Center

4.4/5 (504 reviews)

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.

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