Adventure Holidays in Florida Keys 2026

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Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

10 min walk from Duval Street

Stay at this spa hotel in Key West. Enjoy free Wi-Fi, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their reviews. ...

8.6/10 Excellent! (3,604 reviews)

"Booked this place for the location and how many pools they had. Didn’t know until we got there that the largest pool was under renovation and completely out of service. Not the end of the world but this made the other 2 pools (combined they were the size of the 1 that was closed) more cramped. Then ..."

Reviewed on 15 Sept 2026

Hawks Cay Resort

61 Hawks Cay Blvd Marathon FL

2 hours drive from Duval Street

Stay at this luxury hotel in Marathon. Enjoy free Wi-Fi, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their reviews. ...

8.2/10 Very good! (1,011 reviews)

"Beautiful resort"

Reviewed on 15 Sept 2026

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

3 hours drive from Duval Street

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! (1,440 reviews)

"Clean and comfortable rooms, but I did get a dated feel, but certainly served our purpose. The property supplied EVERYTHING needed to enjoy your stay. I didn’t have dinner there, but their breakfast was elevated and delish. The Adult pool we used had an exercise instructor, a spa and was crystal ..."

Reviewed on 14 Sept 2026

See all 8,297 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.