Amsterdam's Curry Mansion Inn
511 Caroline St.
For a sense of history, try this late-1800s historic mansion complete with antique furniture and enhancements like a complimentary evening cocktail party. Even though the structure operates as an inn, it’s still Florida-style, so the home has a sweeping wraparound front porch, a small swimming pool and hot tub. There’s also a full daily breakfast.Book Now
Hyatt Centric Key West Resort & Spa
601 Front St.
If you’ve ever searched for a place that is upscale without that stuffy, formal edge, this is what it feels like. You can look at the pool or Gulf of Mexico from your lounge chair as the sun sets. You can even bring your furry best friend; the Hyatt advertises itself as a dog-friendly resort.Book Now
Opal Key Resort & Marina Key West
245 Front St.
The property is actually built into the extended Mallory Square dock. This is an ideal location for folks who love Old Town Key West, want to be close to everything. They can then plan to come back to a posh night’s sleep, great amenities and room service.Book Now
Pier House Resort and Spa
One Duval St.
One of the few hotels on the island with its own private beach, the Pier House has a long history of hospitality. Located at the furthest end of Duval Street, this hotel has been a staple in Key West since the 1960s. The hotel features upscale tropical décor and lush landscaped grounds.Book Now