Key West hotels

When it comes to the best hotels in Key West, this gem—home to 40 high-design cottages—is always at the top of my list. Set on an exclusive 27-acre private island full of exotic orchids and bougainvillea, it’s as dreamy as it gets. You can choose from one-, two-, three- and four-bedroom cottages for your stay.

From the wraparound verandas and the private beach to the oceanfront yoga, this place is special. There’s plenty to keep you entertained, too, from a waterfront pool, family activities and a spa (where I recommend the Hydrafacial and a deep-tissue massage). My favourite time of day is mid-afternoon, when a staff member hands out complimentary treats.

Dine at Latitudes for roasted beets, pan-seared yellowtail snapper and grilled centre-cut tenderloin. If you want to kick things up a notch, add a private chef, grocery shopping services or in-cottage massage treatments.

The Capitana is a standout when it comes to the best hotels in Key West. The first thing you’ll notice are the two huge aquatic murals, which both have a serious wow factor. The walls and ceiling of the lobby—festooned with antique brass lanterns, refurbished driftwood fixtures and buried treasure—instantly set the mood.

The coastal theme is carried throughout the suites, with ship lapped walls and tiles reminiscent of sea glass. Family rooms come with a king bed and bunk beds, while cottages offer two king bedrooms, furnished decks, full kitchens and canal views. Kids will appreciate the kayak, SUP and bicycle rentals on site, while adults will enjoy McKee's Tiki Bar, where the classic conch fritters with spicy rémoulade are to die for.

I recommend splurging on a beachside cabana. Stocked with a mini fridge full of complimentary soft drinks and a TV, it’s just made for beachside lounging.

With 30 types of rooms and cottages to choose from across several different properties, Simonton Court Historic Inn & Cottages is one of the most unique hotels in Key West. Set on the sprawling site of a former 1880's cigar factory, the property has a storied past.

The Historic Inn has Dade County pine accents and a black-bottom swimming pool, while The Manor House is a Conch-style shotgun home that has been transformed into a poolside oasis. Last but not least, the 1920's two-storey pink stucco home has suites complete with a pool. In the back of the property, you’ll find the Mansion, the property’s largest swimming pool and a breakfast bar.

My go-to restaurant nearby is Date & Thyme, where you can order açai bowls and avocado toast for breakfast and pesto garden wraps and veggie burgers for lunch.

This boutique hotel in Key West, just a block and a half away from the famous Duval Street, is in the heart of Old Town Key West. The Conch House, a gorgeous restoration of a 19th-century historic bed and breakfast, gives you easy access to the Southernmost Point and the Hemingway House, where I love photographing the many six-toed cats who live there.

From Sealy Posturepedic bedding and on-site bicycle rentals to complimentary breakfast delivered to your room or served poolside, the hotel has carefully thought through all of your needs.

Whether you’re sitting by the pool or chilling in a rocking chair on the porch, it’s easy to see why this is one of the best hotels in Key West. As one of the island’s earliest historic pioneer family estates, arriving here feels like stepping back in time.

There’s so much to love about Santa Maria Suites. Kick back by one of two heated pools in the garden—you can stay for hours thanks to chilled towels, frozen drinks and bottled water served poolside—or head to the Southernmost Beach, two blocks from the hotel, where chairs, towels and umbrellas are at the ready.

The two-bedroom suites here have full kitchens and laundry rooms, so you’ll feel right at home. When you’re ready to explore outside the hotel, I recommend a day trip to Dry Tortugas National Park, home to a marine sanctuary and a former US military fort built in 1847. Get there by chartering an 11-metre luxury adventure boat for up to 13 passengers with Boatsetter.

It’s easy to see why this boutique gem is one of the best hotels in Key West. For starters, guests have four swimming pools to choose from, watersports rentals, on-site dining all day long and easy access to Old Town Key West. The hotel’s shuttle service takes guests to Duval Street and Smathers Beach, where you can enjoy Smathers Beach Club.

Choose from 148 spacious rooms with tropical garden views or water views. End the day at the Kitchen Grove & Bar for the catch of the day and a round of family games, and don’t forget to make time to stop by the Key West Butterfly & Nature Conservancy to see colourful birds and butterflies from around the world.

But my favourite thing about this hotel are the guestroom porches; that, and the fact you can eat an al fresco breakfast by the pool.

One of the best luxury hotels in Key West is Opal Key Resort & Marina. There are so many ways to get in some R&R here: laps in the pool, a soak in the hot tub or sipping island-inspired smoothies.

The hotel’s 178 spacious guestrooms and suites are beach casual and pet-friendly—furry friends receive a gift bag with treats and waste bags on check-in, and rooms come with a dog mat, food and water bowls. No wonder this is considered one of the best hotels in Key West for dog lovers.

Starting in early 2025, the hotel will have an upgraded arrival experience, an expanded pool area and a new restaurant. When you’re ready to venture out, I recommend heading to the Key West Lighthouse and climbing its 88 steps for dreamy views of paradise.

The Marquesa Hotel is one of the best hotels in Key West for history buffs, thanks to the fact it’s listed on the National Register of Historic Places. But that doesn’t mean you won’t find all the modern comforts here: each room has a deep soaking tub and easy access to two on-site pools.

The hotel was once a rooming house and corner grocery store in historic Old Town, so it qualifies as quintessential old-island living. With lush courtyards and three pools, it’s a peaceful getaway. Inside, the 44 luxurious rooms are decked out with dark wood flooring and island-style furnishings. Outside, the pastel blue exterior is reminiscent of the sea.

Save time to eat at Café Marquesa, the hotel’s legendary restaurant, for fresh baked bread, grilled swordfish and frisée salad. Top it all off with key lime pie and beignets dusted with powdered sugar.

The Perry Hotel & Marina has 5-star service down to a tee. That means champagne on the sun deck at check-in, Saturday yoga and concierge service. Rooms are modern with rustic accents and include pillow top mattresses, wood-panelled headboards and outdoor showers.

Rent scooters and bikes on-site, work on your cardio in the fitness centre, or simply watch the boats sail into the marina while soaking in the pool. Animal lovers will appreciate that the hotel is pet-friendly and has two dog parks.

When in Key West, my top priority is scoring ocean therapy time. The best way to do that is with a clear-kayaking tour with Get Up and Go Kayaking, where the unique kayaks make it easy to spot the manatees and dolphins that swim below.

A 5-star, adult-only property, H20 Suites is one of the best hotels in Key West for a romantic getaway. There are 22 suites—11 of which have private plunge pools—with Italian marble bathrooms, spacious rainfall showers, plush robes and king-size beds. The 24-hour concierge can arrange e-scooters and bikes when you’re ready to explore, and nearby you’ll find Mallory Square, the Southernmost point and Duval Street.

The rooftop deck, where you can order island-inspired drinks and tapas, is the place to be. What’s more, from 1 pm to 5:30 pm each day, there’s complimentary wine and sangria at the rooftop pool bar. Local muffins are delivered at turn-down service.

For nature lovers, I recommend visiting the Key West Tropical Forest & Botanical Garden. Bring a picnic lunch and wander through the arboretum and gardens.