Places to Stay

Historic Key West stays on Duval Street—family-owned inns.

The Smallest Bar Inn is an eclectic Duval Street lodging that’s home to Key West’s famously tiny 72 sq ft “Smallest Bar,” offering six cozy accommodation units steps from Old Town’s top attractions.

Mermaid’s Bay is a secluded boutique estate in Islamorada, offering three private waterfront homes with resort-style amenities, ideal for group getaways

Topsider Resort is a unique beachfront retreat in Islamorada, featuring charming octagonal stilted bungalows perched over the bay.

Little Palm Island Resort & Spa is an adults-only private island retreat offering luxury thatched-roof bungalows, gourmet dining, and a world-class spa in the Florida Keys.

Discover Jolly Roger RV Resort: spacious sites, stunning views, and island adventures!

Freewheeler Vacations is the Upper and Middle Keys’ largest and longest-running vacation rental company, offering everything from cozy condos to grand estates, backed by 30+ years of expert service.

Fisher Inn Resort & Marina is an oceanfront boutique resort in Islamorada offering stylish rooms with kitchenettes, a heated pool with ocean views, and unique amenities like its own boat ramp and marina. Ideal for anglers, boaters, and families seeking waterfront comfort.

Center Court Key West offers boutique vacation rentals in Old Town, featuring 9 private suites with heated pools, lush gardens, and a central location just steps from Duval Street.

Parrot Key Hotel & Villas is a tropical oasis in Key West, offering spacious rooms, suites, and villas surrounded by lush gardens, four outdoor pools, and a complimentary shuttle to Old Town attractions.

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.

Boyd’s Key West Campground offers a variety of accommodations including RV sites, tiny homes, and tent camping.

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.

Ocean Key Resort & Spa in Key West offers luxury accommodations with Gulf views, a rooftop pool, three waterfront dining options, and a full-service spa, all located at the iconic Zero Duval Street.