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Top Fishing Florida Keys Hotels

Islander Resort

82100 Overseas Highway Islamorada FL

3 hours drive from Duval Street

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! (1,009 reviews)

Great boutique type hotel with good amenities. Excellent landscaping, lighting and access to amenities.

Reviewed on Mar 2, 2026

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

3 hours drive from Duval Street

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! (1,299 reviews)

This Resort is unbelievable from the rooms to the beach, walking & biking trails, golf course 27 acres of lush property. Lots of shops & restaurants nearby including Bass Pro Shop, small artists shops & brewery within walking/biking distance.

Reviewed on Feb 25, 2026

Captain Pips Marina & Hideaway

1480 Overseas Hwy Marathon FL

2 hours drive from Duval Street

Stay at this hotel in Marathon. Enjoy free WiFi, a marina, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. ...

9/10 Wonderful! (1,002 reviews)

The staff was super friendly and it's really nice to have bikes and kayaks included. It's fairly minor since we only stayed one night but the quality of the unit is pretty rough; giant gaps in the flooring, broken paneling, bed frame is a foot too long for the bed, one of the blinds wouldn't close, ...

Reviewed on Mar 2, 2026

See all 8,300 properties in Florida Keys

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.