Here’s our guide on where to stay when you finally make that journey down to Mile Marker 0.
Situated on Simonton Street, just down the block from the original Marquesa guesthouse, the refined Key West hotel has introduced an addendum to its property with Marquesa 4-1-4 (414 Simonton St.; 800-869-4631), which opened Oct. 2018. Composed of three lovingly restored Victorian-style buildings, the boutique hotel features 17 unique guest rooms — many with kitchenettes, sophisticated furnishings, private balconies and soaking tubs inside spacious bathrooms — surrounded by a central courtyard pool. Current rates from $300.
24 North Hotel
Sister property to The Gates hotel in New Town, 24 North Hotel (3820 N. Roosevelt Blvd.; 305-320-0940) is a revamped motel with a playful, modern design motif drawing inspiration from Key West and Cuba. The name is derived by the line of latitude that the two islands share 90 miles. The property boasts a spacious pool deck with a casual poolside bar and the restaurant Toasted Coconut, as well as a gym, Starbucks and access to The Gates amenities and dining. Current rates from $103.
Ocean Key Resort & Spa
Perched at the foot of Duval Street overlooking the Key West Harbor, Ocean Key (0 Duval St.; 305-296-7701) is Key West’s premiere luxury resort. It’s home to a harborfront swimming pool, marina, Hot Tin Roof fine dining restaurant and the lively Sunset Pier bar adjacent to Mallory Square. Current rates from $206.
The Marker’s (200 William St.; 305-501-5193) debut in 2015 kicked off a period of expansion for Key West’s hospitality scene. The hotel marked the first newly built property on the island in more than 20 years, bringing a dose of modernity to Key West’s famously laid-back landscape. Designed to blend into the neighborhood’s historic Bahamian conch cottages and Victorian-style homes, it has an air of under-the-radar cool in a prime setting on the Historic Seaport. Current rates from $182.
Margaritaville Resort & Marina
The longtime Westin Resort & Marina was absorbed into Jimmy Buffett’s empire and rebranded as Margaritaville Resort & Marina (245 Front. St.; 305-294-4000). You might wonder what took so long, as he’s a key figure in the island’s lore. Current rates from $201.
Hyatt Centric Key West Resort & Spa
Another harborfront legacy property, the Hyatt, has freshened up its brand by joining the Hyatt Centric (601 Front St.; 305-809-1234) collection, which prides itself in offering a launching pad to discover what makes the destination unique. The property features a lagoon-style swimming pool, small beach, spa and restaurant. Current rates from $269.
Part of the Historic Key West Inns Collection, the Cypress House (601 Caroline St.; 305-294-6969) is a delightfully shabby-chic boutique guesthouse with 22 rooms spread across three historic Bahamian Conch cottages and mansions. Rooms are spacious and modern with original wood flooring and paneled walls, charming balconies and oversized bathrooms. Best of all, it’s located just one block off Duval on Caroline Street in the heart of Old Town. Current rates from $140.
Part of the Marriott Autograph Collection, The Saint (417 Eaton St.; 305-294-3200) is a boutique hotel with New Orleans DNA nestled in the heart of Key West’s Old Town. There are just 36 rooms, with a courtyard swimming pool and an intimate cocktail bar off the lobby. The hotel’s eclectic design — a moody, wood-paneled lobby with velour banquettes, bright white guest rooms and Buddha statues by the pool — is playful and inviting, if lacking a cohesive point of view. Current rates from $169.
A boutique hotel located in the heart of Key West’s charming Old Town district, Marquesa (600 Fleming St.; 305-292-1919) is among the most sophisticated options on the island. Each of its 27 guest rooms boasts a unique design, many with high gloss Brazilian cherry hardwood floors and an eclectic mélange of substantial wooden furniture from the West Indies, the Philippines and England. Its eponymous café is widely regarded as one of the best in Key West. You can arrange for freshly baked blueberry banana bread and coffee to be sent to your room for breakfast in bed. Current rates from $300.
Historic Grand Dames
One of Key West’s most recognizable buildings, the Southernmost House is an icon at the southern end of Duval Street just a block away from the Southernmost Point buoy. The historic Victorian manse, outfitted in seafoam green and conch shell pink, is an ornate, 18-room bed and breakfast with a sublime zero entry swimming pool overlooking the Atlantic Ocean. Current rates from $249.
Casa Marina Resort
Conceived by oil tycoon, railroad magnate and South Florida developer Henry Flagler, Casa Marina (1500 Reynolds St.; 305-296-3535) is one of the island’s most historic resorts. Occupying six-and-a-half beachfront acres on the island’s southern edge, its sprawling poolscape is one of the most picturesque in Key West. Current rates from $235.
La Concha Hotel & Spa
The tallest building in Key West at six stories high and one of the most iconic, La Concha Hotel & Spa (430 Duval St.; 305-296-2991) is located in the center of Duval Street amidst all the hubbub. The property features a wine bar, pool and rooftop spa. Current rates from $159.
Stock Island game changers
The Perry (7001 Shrimp Rd.; 305-296-1717) brings a whiff of maritime industrial chic to Stock Island, just north of Key West, known for its boatyards and shrimp boats. The 100-room hotel boasts a deep water marina and multiple dining destinations in a walkable, village-like setting. The onsite restaurant Matt’s is one of the best in town. Current rates from $193.
Ocean’s Edge Hotel & Marina
Ocean’s Edge (5950 Peninsular Ave.; 844-885-7855) opened January 2018 as Stock Island’s first-ever hotel. Built in a Key West vernacular style with tin roofs and large porches, the hotel overlooks the Ocean’s Edge Marina with a stylish al fresco restaurant and swimming pools. Current rates from $164.
When money’s no object
Sunset Key Cottages
The most exclusive destination in Key West, Sunset Key Cottages (245 Front. St.; 305-292-5300) is located on the private island of Sunset Key less than a mile off the island’s western coast, accessible only by private ferry. The island features a beach, pool and spa, as well as the upscale restaurant Latitudes, one of the island’s most romantic restaurants for al fresco dining and sunset views. Current rates from $739.
Save a Buck
Southernmost Beach Resort
A multi-faceted property that includes historic bed and breakfasts, an oceanfront resort and buildings with guest rooms on Duval Street’s southern edge, the Southernmost Beach Resort (1319 Duval St.; 305-296-6577) offers something for many tastes and budgets. It’s anchored by the Southernmost Beach Cafe and one of Old Town’s only public beaches. Current rates from $187..
An acronym for “Not Your Average Hotel,” NYAH (420 Margaret St.; 305-296-6577) offers a novel approach to traveling with groups. Situated inside a charming complex of conch cottages with courtyard swimming pools and a jacuzzi, NYAH’s rooms are bare bones with a flexible layout of bunkbeds that can be arranged to accommodate up to six guests. Twin beds are surprisingly comfortable, and everyone has their own outlet for iPhone charging, as well as a locker stocked with towels. Current rates from $69.
New Town kitsch
Ibis Bay Beach Resort
If it’s mid-century Florida motel kitsch that you’re after, Ibis Bay Beach Resort (3101 N. Roosevelt Blvd.; 305-296-1043) more than delivers. Set on a complex overlooking the shallow salt ponds, the structures are made of coral stone for funky, bungalow-style accommodations, many of which boast direct access to a sandy beach. While the room’s furnishings are no frills, they still exude a playful, colorful decor. The property is anchored by Stoned Crab raw bar and restaurant, run by longtime local chef Paul Menta. Current rates from $118.
Debuting in 2015, The Gates (3824 N. Roosevelt Blvd.; 305-320-0930) pushes the envelope on what it means to be a hip Key West hotel for the modern traveler. Its New Town location literally positions travelers at the gates of Key West. The hotel boasts some of the most stylish rooms on the island, as well as a poolside food truck, rum bar and cigar lounge. Current rates from $158.
This story was updated Sept. 18, 2019 to reflect the most recent room rates, which are subject to change.