10 tropical hotels on Key West you’ll want to book for a relaxing island escape

OSTN Staff

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best key west hotels
  • The southernmost U.S. island, Key West offers a tropical climate, lush gardens, and warm ocean water.
  • Nicknamed the Conch Republic, Key West has distinct hotels, from colorful inns to expansive resorts.
  • The best time to visit Key West is in summer and early fall when prices are low, beginning at $140.

Table of Contents: Masthead Sticky

Sometimes weird, often wacky, but always wonderful, Key West is the southernmost island in the United States. Located in the temperate Florida Straits, it boasts lush tropical foliage, paradisaical weather, and warm waters for diving, fishing, paddle boarding and more.

Every time I visit this magical place I come away deeply impressed by the commitment locals have made to preserving the historic Victorian pastel-painted homes. These looks are replicated in the many hotels that dot Key West, ranging from quirky and eccentric to elegant and sophisticated.

The following represent the best on the island, including highly-rated properties with central locations and great amenities such as pools. Because Key West is not known for its beaches, being without a pool can make a stay rather sticky in the summer and it’s a must for any hotel you book.

Browse all the best Key West hotels below, or jump directly to a specific area:

These are the best hotels in Key West, sorted by price from low to high.

The Gates Hotel Key West

Gates Pool 3 New Chair Color

Book The Gates Hotel Key West

While the historic Old Town is Key West’s most charming district, New Town, at the island’s entry point, has its own distinct vibe and far more affordable hotel options. 

That includes The Gates Key West, an upscale boutique hotel with affordable rates and a star attraction in Rum Row, a buzzy poolside bar and lounge decorated in a funky beach-shack style with a huge selection of rum cocktails. Sample conch every which way at the on-site food truck or puff on a stogie in the cigar lounge. 

Rooms are bright and modern, with hardwood floors, exposed beams, whitewashed pine platform beds, and colorful original photographs by an acclaimed local photographer. Standard King rooms are spacious at 300 square feet, but we recommend upgrading to the Scene category for a private poolside terrace or views of the bay.  

COVID-19 procedures are available here.

Parrot Key Hotel & Villas

ParrotHotel

Book Parrot Key Hotel & Villas

Parrot Key & Villas, with new and refurbished lodgings, offers one of the best values on Key West. The rooms and suites feature three different views: garden, garden/water, and waterfront, and every glance is a feast for the eyes, especially if you’re facing the Gulf of Mexico. The inside is soothing as well, with breezy textiles in shades of whites and neutrals, which makes for a pleasant canvas next to all the outdoor colors. Conch-inspired artwork completes the Key West charm.

While a standard Garden King or Double Queen begins at $239 in the off-season, I suggest booking a Garden Suite or a Waterfront King for a minimal extra investment. Regardless, all rooms and suites have a porch, patio or balcony, in-room Keurig coffee makers, L’Occitane products, and come with access to four beautifully landscaped pools, which are cleansed with minerals instead of chlorine.

COVID-19 procedures are available here.

Simonton Court Historic Inn and Cottages

Simonton Court Historic Inn

Book Simonton Court Historic Inn and Cottages

Simonton Court Historic Inn and Cottages provides one of the most authentic and charming lodging experiences on the island. Stay in your choice of reclaimed historic buildings that range from an 1880s cigar factory to a shotgun Conch house. Room categories are numerous and include double occupancy in the Victorian mansion to quadruple occupancy in wood-framed, pastel-painted cottages. 

Follow the brick pathway through the grounds, which are extraordinary and well-maintained, to explore all four pools and where a lovely, complimentary continental breakfast is served poolside every morning. Aside from free Wi-Fi, that’s about it for amenities. But the inn is a block from Duval Street, and concierge services will help arrange whatever tours and charters you like; the staff overall is extremely helpful and well-meaning. 

COVID-19 procedures are available here.

The Perry Hotel Key West

the perry hotel key west

Book The Perry Hotel Key West

Rustic and handsome, this award-winning resort is named after the “Commodore Perry.” The hotel’s decor scheme is made up of a variety of dark woods, warm brown textiles, and white walls and linens, and recalls the seafaring and shipbuilding days of Old Key West.

Relaxed and roomy, The Perry Hotel Key West is an ideal place to sprawl out for an extended stay, especially if you’re in town to fish, boat, or otherwise take advantage of nature. That’s because the 100-room hotel is located in Stock Island Marina Village, which has 288 private slips and plenty of opportunities to book charters.

You may also swim in two attractively designed waterfront pools, decked out with white umbrellas and teepee-shaped daybeds, and dine at three dockside restaurants. Concierge services help to plan water activities including snorkeling, diving, sailing, fishing, and more.

COVID-19 procedures are available here.

Marquesa Hotel

Marquesa Hotel

Book Marquesa Hotel 

The Marquesa Hotel is my favorite place in Key West. I even seriously considered naming my daughter after it. This boutique resort is made up of a collection of restored historic properties: the main house, or the original Marquesa, and three newly renovated buildings (including a cottage), known as 4-1-4- Marquesa. Situated across the street, they’re clustered around a gorgeously landscaped pool and fountain.

The resort offers three pools, which you have access to wherever you stay, and furnishings reflect the environment with antique reproductions, lots of wicker, and airy, colorful fabrics, as well as updated bathrooms.

Although a standard Queen in the main house with a city view is perfectly delightful, I suggest upgrading to the more private, fresher rooms such as a Balcony Deluxe with a King bed, private covered balcony, two lounge chairs, and a table. Likewise, the Poolside Standards, on the first and second floors adjacent to the main house, feature either a terrace or balcony.

COVID-19 procedures are available here.

The Marker Key West Harbor Resort

Marker

Book The Marker Key West Harbor Resort

Overlooking the Key West Harbor, The Marker debuted in 2014 making it one of the newer properties in town. Contemporary and clean-lined with large-format, refillable Key West Aloe brand toiletries in the bathroom to prevent plastic waste, the hotel offers a variety of room categories, including several ADA-accessible formats. The resort also focuses on sustainability, with several features dedicated to improving the environment.

Very few hotels in Key West, or anywhere in South Florida, feature wall-to-wall, wavy-patterned threads underfoot, but all 96 rooms at the two-acre Marker Waterfront Resort include carpeting. A blue-and-white color scheme is reflected throughout the property, including at the three pools and the pool bar. One of those pools is adult-only, a nice option if you don’t have kids. You might want to get there early, though, to stake a claim on a lounge chair or daybed. Folks hang out all day long, enjoying the poolside service, and talented technicians at the bar will keep you hooked on craft cocktails and tequila tastings. When hunger strikes, dine at Starboard, the waterfront restaurant on-site.

COVID-19 procedures are available here.

Key West Marriott Beachside

Key West Marriott Beachside

Book Key West Marriott Beachside

Tropical outside, majestic inside with stone floors, polished dark furniture, and marble bathrooms, Key West Marriott Beachside is a good all-around destination resort, especially if you’re traveling with a family or group. A 16-slip marina allows ocean access for water sports rentals (kayaks and Jet-Skis) and boat charters. A tiny beach allows for tanning — or sweating — opportunities only, but you can slip into the waterfront pool to cool down. The 24/7 fitness center also looks overlooks the Gulf, so you’ll feel like you’re running outside even when while on the treadmill. Bike rentals are also available. 

In September, book a standard King Room for the lowest prices. But these rooms are sometimes the locked-off extra spaces of suites. It might be wise to indulge in a Presidential Suite with a resort view, which includes a full-service kitchen and dining room, for less than $100 more. You can also request grocery service so you don’t have to take time out of your day.

COVID-19 procedures are available here.

Opal Key Resort & Marina

margaritaville key west

Book Opal Key Resort & Marina

Formerly Margaritaville Key West Resort & Marina, this luxury resort is now part of the Opal Collection. Rooms and public spaces have been reimagined to be less Jimmy Buffett and more welcoming to guests of all ilk. Rooms and public spaces soothe with aqua and blue hues contrasted by sand, wheat, and white colors.

Stay on-site for activities ranging from sunbathing at the pool to the nightly Sunset Celebration, toasting the end of another day in paradise on the Sunset Deck, which overlooks the pier where the crowds gather to do the same. Dine at Bistro 245 or walk the bare five minutes to Duval Street and all that it has to offer.

In low season, standard rooms come with packages (some with drinks, others with breakfast). If you have a family, though, it might be worthwhile to upgrade to a suite with a kitchenette for a couple of hundred dollars extra. What it costs you in room fees will save you when it comes to having quick lunches and snacks on hand to prepare instead of order.

COVID-19 procedures are available here.

Pier House Resort & Spa

PierHouseResort

Book Pier House Resort & Spa

For some of the most comfortable pillowtop beds and updated rain shower bathrooms in Key West, check into the 142-room Pier House Resort & Spa. Originally a 50-room hotel, the resort was built by Key West native David Wolkowsky, who also developed the original Sloppy Joe’s (of Hemingway renown), Pirate’s Alley, and the Original Cigar Factory. Several famous musicians, including Jimmy Buffett and Bob Marley, played gigs in the hotel’s Chart Room Bar, which still serves free hot dogs and popcorn like in the old days.

Rooms come with plantation shutters to keep the room cool or let in as much light as you choose, in addition to coffee and water, bathrobes, and umbrellas for the unexpected tropical storm. Morning coffee at the beach bar, fruit-infused water stations, and a welcome drink are all offered, too.

The spa is also one of the finest on the island, with 10,000 square feet and 10 treatment rooms offering everything from the signature “Milk and Honey” treatment, which includes an exfoliation, body wrap, and scalp massage, to a Thai foot massage. The facility includes a full fitness center, Vichy showers, and cosmetic services.

COVID-19 procedures are available here.

Southernmost Beach Resort

guest room (1)

Book Southernmost Beach Resort

If your idea of Key West is lounging on a brightly-hued Adirondack chair while gazing at the calm Florida Straits, then the historic, mid-century Southernmost Beach Resort will deliver. 

The resort, located in between Duval and Simonton streets, is in a prime location and one of the largest (and priciest) in town, covering six acres and two city blocks. Formerly known as the Southernmost Hotel Collection, it comprises two properties with similar names: Southernmost on the Beach and Southernmost Hotel, as well as La Mer Hotel and Dewey House. The last two are adults-only. The website doesn’t really clarify this, so it’s best to call and ask about the differences in room styles and prices when you go to book.

Charming and relaxed, the waterfront resort features a number of opportunities to park yourself waterside, including two beaches (one private, the other public) and three pools. While there’s a fitness center with the usual treadmills, ellipticals, and weights, the beach and aqua yoga sessions are much more appealing. Likewise, the Petite Spa offers plenty of treatments, but you can also get a massage in a three-sided oceanfront cabana on the beach.

COVID-19 procedures are available here.

Ocean Key Resort & Spa

OceanKeyResort

Book Ocean Key Resort & Spa

With hues of lime, aqua, and turquoise plus rattan and wicker accent furniture running throughout both guest rooms and public spaces, Ocean Key Resort & Spa, a Noble House Resort, truly honors its surroundings.

Self-described as “kitschy,” while still high on the luxury scale, the resort is located between Key West Harbor and Mallory Square, smack in the middle of Old Town. In fact, the address is Zero Duval Street. Think of it as the anchor of Old Town, keeping you firmly embedded in the playground of Key West.

Three restaurants and bars — Hot Tin Roof, LIQUID Pool Bar & Lounge, and Sunset Pier — all offer views and access to the open air, so there’s no excuse not to toast the infamous sunset, as the locals do. For an escape, retreat to your balcony and order in a “Craft and Charcuterie” experience with beer and a cured meat board (keep the board), or “The Ultimate Cuba Libre” with 10 Cane rum, Mexican Coca-Cola, fresh limes, and miniature Cuban sandwiches (keep the Riedel Coca-Cola glasses).

COVID-19 procedures are available here.

More on our methodology for selecting hotels

In addition to the criteria above, I considered the following factors:

My experience: I’ve been living in Florida since 1992 and covering the entire state as a food-and-travel writer for a large variety of international publications and guidebooks. I’ve stayed in many of these hotels and can vouch for their overall experience.

Overall features: The best Key West hotels feature sparkling pools – usually more than one! – waterfront views or hidden Old Town locations, and stunning design elements. They also offer restaurants and bars on the premises that bring in that relaxed, sunset-celebrating, Key West vibe.

COVID-19: We only selected hotels that prioritize the health and safety of their guests with new cleaning policies. Every hotel has its protocol displayed on its website. 

Please note that Florida has lifted statewide restrictions on masking and does not allow private businesses to directly ask about vaccination status. However, many businesses still choose to follow CDC protocols that prioritize the health and safety of their guests with new cleaning policies and masking in public spaces.

FAQ: Key West hotels

Where is Key West?

Key West is the southernmost island in a chain of small islands, called the Florida Keys. It’s part of an archipelago that stretches for 125 miles into the Florida Straits, only 90 miles from Cuba. A place known for its distance from large metropolitan influences, it’s attractive to free-spirited thinkers, artists, writers, musicians, and other creative spirits.

Key West is also a port of call for cruise ships, and famously only 90 miles from Cuba. The Conch Republic, so nicknamed because of its Bahamian ancestry, welcomes characters of all kinds and was once home to the likes of Ernest Hemingway, Elizabeth Bishop, and Tennessee Williams. Key West is famous for its candy-colored Victorian and Queen Anne houses, eclectic bars, and spectacular sunsets. It’s also beloved for eccentric residents including six-toed cats and roaming roosters.

What is the best location to stay in Key West?

There are many hotels in Key West, many of which are housed in what are generally called conch houses and built from wood. The architectural style also includes Victorian homes with gingerbread trim, pastel-painted cottages, and roomy double-stories with wraparound porches.

If you want to be within walking distance to Duval Street and all the action, stay in Old Town, where you can also gaze at the singular Conch Republic architecture just by stepping out the door. Key West Bahama Village is just as colorful, with roots extending back to the Caribbean.

The residential The Meadows and Casa Marina Area, home to Higgs Beach, the Dog Park, and White Street Pier, are both distinct and charming, as is Truman Annex, a former naval station that is now a gated community adjacent to the Little White House, Ft. Zachary Taylor State Park and the Truman Waterfront.

If you prefer water views, New Town along the Florida Bay is right up your alley, or if you want a little history, look to the Key West Historic Seaport District

What is there to do in Key West?

For starters, think about hopping on the Key West Old Towne Trolley, which offers tours of the island and is a helpful way of getting around to popular attractions such as the Key West Aquarium, Mallory Square, The Ernest Hemingway Home & Museum, Key West Shipwreck Treasure Museum, Tropic Cinema, Audubon House & Tropical Gardens, Harry S. Truman Little White House, and The Custom House. That’s just a sample of the natural and historic attractions packed into this tiny island, in addition to the long-running bars and entertainment venues like Sloppy Joe’s, The Green Parrot, and Hog’s Breath Saloon, as well as all that the marinas offer in terms of fishing charters and water sports rentals.

Of course, it’s worth keeping in mind that interspersing indoor activities with outdoor ones is important during the hot summer months. And keep in mind that with the hot weather comes hurricane season. From June 1-November 30, Key West does see its share of storm watches/warnings as well as actual storms.

Do I need a car in Key West?

The short answer here is yes. At least, you need a car to get to Key West. Unless you’ve arrived by bus, boat, or seaplane, there’s no other way to arrive on the island. Many visitors fly into Miami International Airport, which has 14 car rental agencies on site, then head south.

Once you’re on Key West, you don’t necessarily have to drive, depending on where you’re staying. But ride-sharing services aren’t as expedient or as numerous as they are on the mainland. A lot of visitors like to walk or bike to destinations. You can also hop on-hop off the Key West Old Towne Trolley or hail a pedicab, a longtime Key West tradition.

Are Key West hotels expensive?

Like other hotels in Florida, expect to see the highest prices in winter and spring when many vacationers are traveling during spring break, school vacations, or simply want to escape cold weather.

In summer, room prices fall to $239. In winter, expect them to rise a few hundred dollars. November through March are generally the priciest months, with rates varying wildly depending on the day and week. Also keep in mind that most, if not all, properties have daily resort fees, usually ranging between $30 to nearly $50 per day. Also note that almost all hotels have a minimum age requirement, ranging from 21-25, for check-in that is not only posted but enforced. This is to keep Spring Break mayhem out of the area and young people will be asked to prove it or lose their reservation if they don’t have ID.

Are hotels safe and open?

Yes, and experts say that hotels are safe, provided you take the necessary precautions outlined by the CDC. Additionally, the CDC says fully vaccinated people can safely travel in the US. All the hotels on this list are open and accepting guests.

That said, the state of Florida has lifted governmental restrictions and COVID protocols. Still, some private businesses opt to follow the CDC masking and social distancing guidelines and may enforce their own rules.

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