Luxury Holidays in Florida Keys 2026

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Hilton Key West Resort & Marina

5950 Peninsular Avenue Key West FL

10 min drive from Duval Street

Stay at this luxury hotel in Key West. Enjoy free Wi-Fi, 6 outdoor pools and a marina. Our guests praise the pool and the restaurant in their reviews. Popular ...

9/10 Wonderful! (1,821 reviews)

"Nice and comfortable"

Reviewed on 20 Sept 2026

The Marker Key West Harbor Resort

200 William Street Key West FL

10 min walk from Duval Street

Stay at this business-friendly hotel in Key West. Enjoy free Wi-Fi, 3 outdoor pools and breakfast (surcharge). Our guests praise the pool and the helpful staff ...

9.2/10 Wonderful! (1,015 reviews)

"Room at arrival was clean, but after not being washing"

Reviewed on 19 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 ...

See all 8,273 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.