Florida Keys Luxury Holidays 2026

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Top Luxury Florida Keys Hotels

Hilton Key West Resort & Marina

5950 Peninsular Avenue Key West FL

26 min drive from Florida Keys Beaches

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 ...

The Marker Key West Harbor Resort

200 William Street Key West FL

36 min drive from Florida Keys Beaches

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! (1,011 reviews)

"Loved it!"

Reviewed on 8 Aug 2026

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

3 hours drive from Florida Keys Beaches

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 8,267 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.