Our island’s history may be a little rough around the edges, but the Key West of today is a luxurious playground at the gateway of the Caribbean. From award winning spas and private beaches to lavish restaurant menus and posh pools, the problem isn’t finding a luxury hotel it’s choosing which one!

Southernmost House
In a neighborhood known for all things “southernmost,” the Southernmost House punctuates the southern end of Duval Street with its deliciously colorful three-story facade. This waterfront grand dame of a bed and breakfast was built in 1896 and is located steps from the Southernmost Point – the most photographed icon on the island. The House’s 18 elegant rooms are beautifully appointed with hardwood furniture, including four-poster beds, and tasteful tropical accents. The luxurious oceanfront pool is flanked by palm trees and alabaster statues, with plenty of lounge chairs. The poolside open-air pavilion provides incredible ocean views and is a picturesque destination for events and weddings. Continental breakfast is served daily, and you’re within walking distance to numerous restaurants.

Location: 1400 Duval St, Key West, FL 33040

Ocean Key Resort and Spa
It’s no wonder this resort has been named among the best in the world by Conde Nast and Travel + Leisure. Ocean Key Resort anchors the northern end of Duval Street and is home to the famous Sunset Pier, where locals and visitors dine, drink and dance over the water. The resort’s spacious rooms are exquisitely decorated with a tasteful tropical flare and the aquamarine palette of their recently renovated LIQUID pool bar lounge melts perfectly into the backdrop of the ocean. Soak in a Japanese tub on a private balcony at their spa before getting one of their signature massage services. Dining at their restaurant Hot Tin Roof is unforgettable with breathtaking views from the second story of the resort.

Location: 0 Duval St, Key West, FL 33040

Casa Marina Resort Key West

Casa Marina Resort
The brainchild of the early 20th century railroad tycoon Henry Flagler, the Casa Marina is a slice of history nestled in a quiet Old Town neighborhood – an ideal location for those wanting to be close, but not too close to the action of Duval Street. This palatial resort boasts the largest private beach on the island and its impeccably landscaped grounds are a popular place for weddings and events. Enjoy a signature Ocean Breeze Massage on the beach beneath an open-air cabana, or sip a cocktail by one of the resort’s two pools. Rooms are bright, airy and modern, with warm neutral undertones. With several waterfront dining options, you’ll experience first hand that Casa Marina means “house by the sea.”

Location: 1500 Reynolds St, Key West, FL 33040

Pier House Resort and Spa
The Pier House Resort is a serene oceanfront enclave nestled near busy Duval Street and the historic seaport. With several room types to choose from, many include private balconies with incredible views of Key West harbor. If it’s a culinary adventure you’re after, try the resort’s restaurant One Duval which features elegant three and five-course tasting menus. Enjoy live music at the Beach Bar, sun-sational views at the Harbor View Cafe or rub elbows with the locals at the Chart Room bar (which serves free peanuts, popcorn and hotdogs!). You can relax by the pool, or better yet at the private beach and swim area. Looking for even deeper relaxation, pamper yourself at the on-site spa and steam rooms!

Location: 1 Duval St, Key West, FL 33040


The Marker Waterfront Resort
The Marker Resort opened to much fanfare in December 2014 as the first luxury resort to be built in Old Town in 20 years. The 96-room resort is quite literally tucked into the historic seaport at Key West Bight, mere steps from the harbor walk and plenty of waterfront dining. Music from local watering holes can be heard from balconies that provide postcard perfect views of sailboats and yachts. Lounge by one of the resort’s three pools or sip tequila and dine al fresco at the poolside Cero Bodega California-Mexican fusion restaurant. The resort does well to pay homage to the island community; its bright modern rooms feature artwork by local Key West artists and each minibar includes a locally distilled rum!

Location: 200 William St, Key West, FL 33040

Sunset Key Cottages
Aptly named, Sunset Key is the private island silhouetted by the setting sun in many a Key West sunset photograph. Though only 500 yards off Key West you’ll feel worlds away at this 27-acre lush private retreat where homes and cottages are available for nightly rental. Latitudes restaurant is a favorite among locals and visitors alike, and the al fresco oceanfront dining view is unbeatable. Even if you’re not staying on the island, you may dine here with a reservation. Resort guests may take advantage of the spa, private beach and two tennis courts. You’ll find everything you need here, and can even have groceries delivered to you from Key West! A small ferry is available to shuttle guests back and forth from Key West 24-hours a day.

Location:  245 Front St, Key West, FL 33040

Last Updated 03/18/2024