With a “come as you are” spirit and turquoise waters, Key West, the island at the southernmost point of the continental U.S, offers a breezy tropical escape. However, it is much more than simply ‘Margaritaville’ as singer-songwriter Jimmy Buffet famously wrote in 1977. It has long attracted artists and writers from novelist Ernest Hemingway—whose 1850s era home you can still visit—to Judy Blume, who owns a bookstore on the island today.
The heart of Key West, the Old Town district, is lined with wooden cottages and Victorian-style mansions shaded by palm trees and dripping with fuchsia bougainvillea. While Key West has a wild side demonstrated by the nightly sunset celebrations at Mallory Square and the raucous bars lining Duval Street, if you look beyond the beaten path you will find a more subdued and sophisticated slice of island life. There are locally owned restaurants, boutiques, art galleries and a plethora of stylish hotels, from a brightly hued boutique hotel in a historic mansion to a barefoot resort that is perfect for families. If you're looking to explore the rich history this island has to offer, here are our picks for the best hotels in Key West.
A view of the Ocean Key Resort's Sunset Pier Bar
At the foot of Duval Street on the Key West Harbor, Ocean Key Resort and Spa is the stuff Key West vacation dreams are made of. There’s a brilliant blue pool that mirrors the color of the ocean, the Sunset Pier bar juts out into the harbor (offering unobstructed sunset views) and the hotel offers the island’s best spa. SpaTerre specializes in Balinese and Thai treatments like a rice and turmeric skin scrub followed by a flower petal bath. The resort’s signature fine dining restaurant, Hot Tin Roof, serves an elevated take on the island’s classic “Floribbean” fare—think seared black grouper in coconut curry and crispy whole yellowtail snapper.
Ocean Key Resort has a breezy beach house aesthetic with polished limestone floors, rustic wood-paneled ceilings and cool-toned turquoise and lime furnishings. As an added bonus, each of the resort’s 100 rooms and suites boast balconies with full or partial harbor views.
A Junior Suite at the Marquesa Hotel.
The Marquesa, a boutique hotel in the heart of Old Town on Fleming Street, is one of Key West’s most sophisticated and well-placed lodgings. There are just 27 rooms inside four restored conch cottages dating back to the late 1800s with tin roofs, pastel siding and white wraparound balconies. The lushly landscaped grounds, including two secluded swimming pools shaded by palm fronds, induce even the most harried travelers to rest and relax. Spacious rooms, including standard rooms, balcony rooms and suites, have Brazilian cherry hardwood floors and antique reproduction furnishings sourced from the West Indies and the Philippines and modern bathrooms. Locals and visitors love Café Marquesa for its elegant atmosphere (hand-painted trompe l’oeil wall, large mahogany-framed mirrors) and inventive preparations of local seafood like basil blue crab with saffron aioli.
A room at the Grand Maloney.
The Grand Maloney opened in May 2022 and is a stylish addition to the island. The local owners preserved the 19th-century mansion built for Key West’s “Sponge King,” but updated interiors with luxurious finishes and designer furniture. The handsome home-away-from-home has a wraparound patio, brick façade and a mint green lobby with 11-foot-high ceilings. Color is a predominant theme in each one-0f-a-kind room. The light-filled Red Room has a scarlet ceiling, brick fireplace and black marble bathroom while the Yellow Room has a glossy yellow shower and a plush emerald green bed frame. With just five guest rooms and a freestanding carriage house with an exposed beam ceiling and private terrace shaded with native poinciana trees, the hotel is available for a full property buyout. While there’s no restaurant, the best of Key West is a stone’s throw away on Duval Street.
A patio view at the Marker Hotel in Key West, FL.
The design of the Marker, on Key West’s Historic Seaport, succeeds in bringing the watery hues and breezy style of Key West indoors. Large, modern guest rooms have bright blue blankets, water-reminiscent carpets and crisp white walls and linens. Most rooms have balconies for soaking in Key West’s balmy ocean breeze. For full water immersion, book a Harbor View room which offers views of sailboats bobbing in the sea. The hotel truly offers the best of Key West from the iconic architecture (tin roofs and white porticos) to the climate appropriate cuisine—including fish tacos and a key lime colada.
A beachfront view from Sunset Key Cottages in Key West, FL.
If your idea of island living includes a more quiet residential feel, pass over Key West’s Old Town and book one of 40 cottages at Sunset Key. The hotel on 27-acre Sunset Key Island, a ferry ride away from Key West, is the Key’s most exclusive destination. Couples with bronzed skin laze the day away on the hotel’s private beach, work up a sweat on the tennis court and cool off with a dip in the lagoon-style swimming pool. Cottages, ranging from one- to four-bedrooms, have wraparound porches and balconies, masculine wooden bed frames and full kitchens with quartz countertops and stainless steel appliances. Some cottages even boast private pools. Make a reservation at Latitudes restaurant at golden hour a meal of fresh fish and to see natures stunning sunset show.
The walkway leading to the swimming pools and beach for guests.
Oil tycoon Henry Flagler, who also built the Overseas Railroad connecting Key West to the mainland, created the Mediterranean Revival-style Casa Marina. With 6.5 oceanfront acres, stucco arcades and a Spanish tile roof, the resort on the National Register of Historic Places channels the glamour of the Roaring Twenties. The hotel officially opened on New Year’s Eve 1920 and has been a favorite of celebrities and visiting dignitaries ever since. The high-ceilinged lobby has Cypress wood beams and columns and glossy hardwood floors. And while guest rooms with neutral contemporary furnishings are a bit basic for such an opulent historic structure, all is forgiven at the elaborate poolscape where two symmetric pools flank a wide walkway leading to the 1,000-foot-long soft sand beach reserved exclusively for guests.
A room with a view at the Perry Hotel.
Separated from Key West by the narrow Cow Key Channel, Stock Island is the area’s last working waterfront and feels more industrial than the rest of Key West. The Perry Hotel and Marina, which opened in 2017, gives travelers unprecedented access to this slice of “old Key West” where longtime Keys families, fishermen and artists reside. There’s nothing old timey about the clean lined hotel with plenty of raw concrete, exposed steel and natural wood. With its location in Stock Island Marina Village, fishing and boating charter possibilities are endless. The hotel’s excellent Matt’s Stock Island Kitchen and Bar (where fresh seafood featured in dishes like cioppino and shrimp and grits comes directly from the working boats on the waterfront) is worth visiting even if you’re not staying at the hotel. Hotel guests can also lounge by the waterfront pool and sip a cocktail by the fire pits at sunset.
A guest room at Ridley House.
Kimpton Key West is comprised of five distinct boutique hotel experiences spread across Old Town. Each property including the Ridley House (comprised of three historic homes), Winslow’s Bungalows (the largest at 85 rooms), the Lighthouse Hotel (near the historic Lighthouse and Hemingway’s former home), Ella’s Cottages and Fitch Lodge offers an Old Town oasis with lushly landscaped courtyard pools and updated designs. Kimpton designers chose nautical nods, such as a palette of soft blue and cream, summer cane beds and basket lighting, and preserved original features like stained glass windows and spiral staircases to give the hotels a unique but cohesive look. Each property treats guests to complimentary breakfast and Winslow’s Bungalow and the Lighthouse Hotel have lively pool bars.
Before I launched my career in journalism and travel writing over a decade ago, I worked for a water sports company in Key West and spent my days taking passengers snorkeling at the reef, sunset sailing and parasailing. My favorite destinations include boating and beaches, whether that's sailing the Mediterranean from Sardinia to Corsica or spearfishing in uncharted waters in the Bahamas. With a firm belief that where you stay sets the tone for your trip, I love discovering new hotels. Over the years, I've checked into nearly every hotel in South Florida. Today, I split my time between Manhattan and South Beach, and I get back to Key West frequently. My writing has appeared in Condé Nast Traveler, Afar, Nat Geo Traveler, the New York Post and Catamaran Literary Reader.