Places to Stay

Charming historic cottages in the heart of Old Key West, steps from Duval Street!

Hampton by Hilton Marathon: Florida Keys getaway with pool, breakfast, WiFi.

Key West Historic Inns — a curated collection of five distinctive, historic properties in Old Town Key West offering boutique stays steeped in island charm.

Orchid Key Inn is an adults-only boutique hotel on Duval Street, offering stylish rooms, a tropical pool with a hot tub, and a vibrant poolside bar, all within walking distance of Key West's top attractions.

Matecumbe Resort is an oceanfront, family-friendly resort in Islamorada, offering fully equipped suites, a heated pool, private beach, and complimentary kayaks and bicycles.

The Reach Key West, Curio Collection by Hilton, is a luxurious beachfront resort situated on the island's only private natural sand beach.

Blue Flamingo Resort in Key West offers a reimagined getaway with tropical-style rooms, two lively pools with luxe cabanas, and poolside dining at Rum Row and Toasted Coconut.

Dove Creek Resort & Marina is a tropical retreat in Key Largo offering ocean-view accommodations, a heated outdoor pool, complimentary breakfast, and a marina with water sports rentals. Guests can enjoy snorkeling, kayaking, and fishing activities.

Oceans Edge Key West Resort & Marina is a luxury waterfront resort on Stock Island, featuring six heated saltwater pools, a 165-slip marina, an on-site restaurant, and complimentary shuttle service to Old Town Key West.

Historic Hideaways offers a curated selection of private Key West vacation homes, including cottages, townhomes, and historic residences, many with private pools.

Discover a curated selection of vacation homes in Marathon, FL, featuring private pools, docks, and waterfront views. Ideal for families and groups seeking a relaxing Keys getaway.

Discover a historic Key West icon blending vintage flair with modern luxury.