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Top Adventure Florida Keys Hotels

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

10 min walk from Duval Street

Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...

8.8/10 Excellent! (3,248 reviews)

This was my second time staying at Southernmost. It really is a lovely property, with a fun vibe and extraordinary location. That said....when we checked in, as an Expedia VIP and Platinum member, I was told I was eligible for a room upgrade, but not until the 2nd night of my 4 night stay. When we ...

Reviewed on Apr 27, 2026

Hawks Cay Resort

61 Hawks Cay Blvd Marathon FL

2 hours drive from Duval Street

Book a stay at this luxury hotel in Marathon. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...

8.2/10 Very Good! (1,009 reviews)

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Reviewed on Apr 27, 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! (1,314 reviews)

Everything

Reviewed on Apr 24, 2026

See all 8,298 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.