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

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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.

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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

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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

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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

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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

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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

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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

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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

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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)

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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.

More of the best Florida hotels

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The 11 best Airbnbs in Key West from charming cottages close to Duval Street to tranquil stays on private beaches

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Best Airbnbs in Key West

  • Key West is one of the most popular US destinations thanks to its laid-back, tropical vibe.
  • Its stunning beaches are family-friendly, but it’s equally great for couples and solo travelers.
  • We rounded up the best Airbnbs in Key West, ranging in price from $147 to $513 per night.

As a long-term Florida resident, my family and I love to take the three-hour road trip down from Miami to Key West. It’s one of those places that we find ourselves returning to year after year thanks to its beautiful beaches, historic attractions, and fantastic food. Plus, it offers many travelers the chance for a tropical paradise with no passport necessary.

Key West is only about four miles long and two miles wide, and most of the shopping, dining, and nightlight is situated on Duval street, the main road that runs down the middle of the island, from the Gulf to Mexico to the Atlantic Ocean.

Whether you want to be at the heart of the action or opt for a more tranquil beach getaway will largely dictate the best location for your stay. Luckily, there are plenty of options regardless of your preference.

Browse all of the best Key West Airbnbs below, or jump to a specific section:

Here are the best Airbnbs in Key West, sorted by price from low to high.

Central-based studio one block from Duval

Best Airbnbs in Key West - Central based studio one block from Duval, $147

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Located just one block from Duval Street, this studio apartment is an ideal base for a quick getaway. There’s also a private parking spot, which is a serious perk when visiting Key West as parking comes at a premium. 

This first-floor studio is small but well laid, with a Queen-size bed and a separate kitchen and dining area, complete with granite countertops. A large wooden wardrobe easily allows travelers to unpack and settle in. The unit is part of a historic building and though simple in decor, it has all the necessities and even boasts a deck with a small sitting area. Past guests rave about the property’s cleanliness and its proximity to many of Key West’s major attractions. 

Visit the famous Sloppy Joe’s Bar, opened in 1933, or the nearby Key West Butterfly Nature Conservatory. You’ll also find plenty of shopping and restaurants right nearby. 

Colorful condo steps from Duval

Best Airbnbs in Key West

Book this Key West Airbnb 

The huge deck and central location make this condo in downtown Key West a prime choice. Aptly named Bella Vita, or “good life,” the property has a wrap-around porch with white Adirondack chairs for relaxing or some good old-fashioned people watching during downtime.  

The interiors are decorated in bright, cheery colors, including orange and turquoise walls, a red leather sofa, and blue accent pillows. The large master bedroom has a King-sized bed, a desk/vanity space, matching bedside tables, and a sound machine to enjoy a peaceful sleep. and the bathroom has an indulgent frameless glass walk-in shower. The galley-style kitchen includes bar seating at the kitchen counter. 

The ground-floor condo is also close to nearby bike and scooter rentals, so you can cruise around the island in style. 

Cheerful condo near Mallory Square

Best Airbnbs in Key West - One bedroom condo near Mallory Square, $280

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With a large, shaded balcony overlooking the nearby cluster of Victorian-style homes and located within a quiet gated community in the Truman Annex, it’s no surprise that this listing gets a near-perfect rating. 

The inside of the condo is painted in bright yellows and blues, creating a sunny vibe that matches its location. The living area is found upstairs and includes plenty of seating options for lounging around, including a contemporary sofa lined with oversized pillows and a velvet armchair.   

The dining area seats up to five, and the kitchen was recently updated with white shaker cabinets and gray stone countertops. There’s a porthole above the kitchen sink that gives it a slight maritime theme, which continues with seascape art and a floor-to-ceiling bookcase filled with model ships and starfish. 

The historic Hemingway house, Maritime Museum, and Truman White House are all close by. The condo is also a short walk to Zachary Taylor Park, one of the top public beaches in Key West. Bike rentals are only a block away, and the condo includes bike storage for guests.

Modern townhome right on Duval

Best Airbnbs in Key West - Two bedroom townhome in the heart of Key West, $225

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This large townhome puts guests at the heart of the action, thanks to its location right on Duval. Large spaces at this price point are hard to come by in Key West, so this property is a gem for families or larger groups. The inside has been recently renovated with calming neutral tones and standout features include two comfy couches with pops of colorful pillows and a round wooden dining table that seats five.  

There’s a parking spot included, although you probably won’t need your car during your stay since many of the most famous Key West restaurants, like DJ’s Clam Shack, are only feet away. 

The lower level of the townhomes includes an open floor plan with a kitchen, dining room, and full bathroom. Upstairs, the pitched roof makes the bedrooms extra cozy and there’s also a sitting nook. 

Secluded hideaway with a private hot tub

best Airbnbs in Key West - Secluded "mango" hideaway with a private deck, $311

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Tucked away in historic Old Town, this quaint cottage is great for those who want want to be close to the action on Duval Street (only half a block away), and who also value their privacy. 

The space is decorated in a tropical theme with green and turquoise linens and dark wood furniture. The kitchen features new cabinets, granite countertops, and full-sized stainless steel appliances. There’s also a deep brown leather sofa bed in the living room that’s within eyesight of the open-plan bedroom. Both the bedroom and the living room have large French doors that lead out to the deck, creating a relaxing indoor/outdoor setup when fully open. 

The spacious deck is the real selling point of this property, with a four-person jetted hot tub,  rattan patio seating, and a grill for making meals al fresco. The property even includes a large mango tree that has been lovingly preserved by being integrated into the design of the deck. 

There’s also a shared pool about a block away, and the cottage is within walking distance to the famed Cuban Coffee Queen and the free Duval shuttle bus.

Cozy cottage with a hot tub

Best Airbnbs in Key West - Cozy cottage with a hot tub, $243

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A great property for families, this large cottage is loaded with rustic charm, from the wood paneling throughout the kitchen to the retro bathroom fixtures. Each bedroom is outfitted with a plus, King-sized bed, and the living room boasts a comfy sofa and side chair along with a dedicated workspace.

The home has a fenced backyard with a beautiful garden area. The outdoor oasis includes a private hot tub, a bamboo enclosed outdoor shower, and a patio dining set that seats four. 

It’s tough to beat the location, just one block from Duval street, and there’s a parking spot included. The cottage is also walking distance to Mallory Square, which is home to the best street entertainers and sunsets in Key West. If you’re a pet owner, you can bring your pooch to this dog-friendly property. 

Oceanfront studio on a private beach

best airbnbs key west oceanfront studio

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This second floor, oceanfront studio is a rare property in Key West at this price point, which means that bookings fill up quickly. The condo has a King-sized bed and a large balcony that overlooks the Atlantic ocean. As an added bonus, the home also includes access to the pool and hot tub on the property grounds, though these are shared amenities. 

Visitors will get the best of both worlds with the beach and nightlife right at their fingertips, as this condo is just a five-minute walk to Duval street. There’s also a free garage parking spot that comes with a unit. The studio sits on its own stretch of private beach, so guests can go for a swim or lay out on lounge chairs that are provided by the property. 

Inside there’s a collection of wood and wicker furniture and a plush armchair in soft, pastel tones. The bedroom has four plantation shutters that look out to views of the ocean and ample closet space to unpack. There’s also a small fridge and microwave at your disposal, though there isn’t a full kitchen. 

Spacious sailing yacht

Best Airbnbs in Key West - Three bedroom sailing yacht, $224

Book this Key West yacht Airbnb 

One of most unique properties in Key West, this spacious yacht is ideal for adventurous travelers. Nicknamed “The Someday Soon”, the yacht features three sleeping areas with a setup that’s especially ideal for families, including a Queen size bed in the aft cabin, a Full-size bed in the midship, and two Twin beds in the forward cabin. 

The yacht is a vintage Mason boat with a mid-century modern interior that includes turquoise accents, carved wood trim, and polished wood floors. The eating area has a comfy breakfast nook and large windows that open up to let in the light. If you want to eat your meals on board, there’s a four-burner gas stove, an oven, and a refrigerator and freezer in addition to a grill on the deck. 

The full-size bathroom has a shower and lots of storage space under the sink. While the vessel is roomy inside, there’s also lots of seating outdoors. The cockpit is furnished with taupe and turquoise cushions and pillows, making it an ideal reading retreat.  

As an added option, the booking comes with a day sail, and the marina can provide a captain at an extra charge. Guests are also welcome to use the marina amenities like the heated pool and the gym.

See more of the best boat Airbnbs

Tropical Old Town bungalow close to the beach

Tropical Old Town bungalow close to the beach, $304

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Step inside this breezy bungalow located in between Key West’s Art Gallery District and the Historic District, two pedestrian-friendly areas of Key West. 

The interior of the unit is bright and airy, decorated in complementary shades of coral, lime green, and blue. The main living area has an open floor plan and the kitchen has a two-tier island that overlooks the living room. Relax on the cream-colored couch that’s adorned with palm leaf printed pillows under a palm leaf fan to really get into beach mode. 

A matching palm leaf fan is found in the bedroom, which also boasts an elevated deck with a hot tub and high-top dining setup. Back inside, the bathroom has a spacious walk-in shower, and there’s a full-size washer/dryer in the hallway. 

There’s a shared courtyard space with a pool and a grill, and the property is also less than a mile from the beach, so after you settle in, you can make a beeline for the warm waters.

Historic Key West suite in Old Town

Best Airbnbs in Key West - Historic Key West suite in Old Town, $447

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Guests staying at this property get to experience a piece of Florida history. This suite is part of a property in Old Town that was built in 1889, and it’s only three blocks from Duval Street. 

Though technically a guesthouse suite, the first-floor accommodation has its own entrance and is entirely private. The kitchen has modern appliances, warm recessed lighting, and a dining area with an expandable table. In the sitting area, there’s a loveseat that can fold out into a bed and a folding screen that can be used to create a private sleeping space.

Outside, there’s an expansive deck and a wicker patio set with a coffee table and an ottoman, ideal for sipping coffee in the morning or cocktails in the afternoon. The grounds of the yellow guesthouse feel like a secret garden, with a brick path winding around the tropical landscaping to a pond. Guests can also access a pool that’s shared with other units. Past guests have described this listing as a “tropical paradise.”

Floating Tiki suite

coolest airbnbs key west floating tiki suite

Book this floating Key West Airbnb

Designed to be a glamping experience on the water, you get to this one-of-a-kind floating suite via boat or water shuttle.

The provided paddleboards and snorkel gear make it easy to leap off the front deck and hit the surrounding water. Of course, lounging in the hammock or opening the French doors on all sides to take in the water views from the King bed are also worthy options. 

Brazilian hardwood floors complement the thatched-tiki styling and soaring vaulted ceilings give the living space an airy feel — literally since they also serving as the core component to the self-ventilating design that helps keep this suite cool. While there is a bathroom, there’s no true kitchen here. There is a cooler that can keep food cold for up to nine days, but guests need to bring their own ice and supplies.

FAQs

What is there to do in Key West?

You won’t want to miss dining at Blue Heaven and Santiago’s Bodega in the Bahama Village, and no trip is complete without stopping in for a slice at the Southernmost Key Lime Pie Shop on Duval. Get a dose of culture at The Key West lighthouse and The Key West Museum of Art and History, or do as we do and take your kids to Mallory Square to watch the various street performers and the sunset celebration that takes place every night. 

Some of our favorite beaches are Smathers Beach and Fort Zachary Taylor Beach, which is a National Historic Landmark and home to a Civil War fort. 

What is the best area to stay at in Key West?

This depends on what vibe you prefer. For a lively party scene close to the action, you’ll want to be right on or very close to Duval Street. Most visitors will also want to spend the majority of their time close to the historic Old Town. It’s where many of the top attractions are, plus it’s easy to get around on foot so you won’t have to be tied to a vehicle or public transportation.

What’s the best time of year to visit Key West?

Between March and May (with the exception of busy spring break weeks) provides one of the best times to visit Key West since there are fewer crowds than during the peak winter season and prices often drop a bit. The weather is also lovely during this time, with April averaging highs of 82 degrees and lows of 72 degrees Farenheit.

Winter is typically the busiest season when East Coast snowbirds seek a warm-weather getaway, so be prepared to pay peak prices if you visit from November to March.

More great Florida Airbnbs

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The 10 best Airbnbs in Key West including a yacht, a cottage with a hot tub, and an oceanfront condo

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Best Airbnbs in Key West - One bedroom condo steps from Duval, $250

  • Key West is one of the most popular US destinations thanks to its laid-back, tropical vibe.
  • Its stunning beaches are family-friendly, but it’s equally great for couples and solo travelers.
  • We rounded up some of the best Airbnbs in Key West, ranging in price from $147 to $447 per night.

As a long-term Florida resident, my family and I love to take the three-hour road trip down from Miami to Key West. It’s one of those places that we find ourselves returning to year after year thanks to its beautiful beaches, historic attractions, and fantastic food.

Some of our favorite beaches are Smathers Beach and Fort Zachary Taylor Beach, which is a National Historic Landmark and home to a Civil War fort.

Key West is only about four miles long and two miles wide, and most of the shopping, dining, and nightlight is situated on Duval street, the main road that runs down the middle of the island, from the Gulf to Mexico to the Atlantic Ocean. Whether you want to be at the heart of the action or opt for a more tranquil beach getaway will largely dictate the best location for your stay.

Regardless of where you’re based, you won’t want to miss dining at Blue Heaven and Santiago’s Bodega in the Bahama Village, and no trip is complete without stopping in for a slice at the Southernmost Key Lime Pie Shop on Duval. Get a dose of culture at The Key West lighthouse and The Key West Museum of Art and History, or do as we do and take your kids to Mallory Square to watch the various street performers and the sunset celebration that takes place every night.

While Key West offers a tropical paradise with no passport necessary, it’s important to remember that there’s still risk involved with traveling during the pandemic. It’s always important to follow guidelines from the CDC, wash your hands, wear a mask, and social distance. Also consider if you’re traveling to or from a hot spot area and take extra precautions if so.

With that in mind, if you do decide to soak up some sun in Key West, Airbnbs can be a safer option for travelers right now because of the added space and limited interactions with others.

We rounded up the best Airbnbs in Key West based on the following criteria:

  1. All listings are for the entire home, per current expert safety recommendations.
  2. All listings have at least a 4.7 rating and excellent recent guest reviews.
  3. We’ve chosen properties that range from $147 to $447 per night, but beware that through the end of March is considered peak season for this area, when prices tend to be at their highest.
  4. While all of the properties listed have some availability as of the time of publishing, keep in mind that because of its popularity, properties in Key West are often booked months in advance, so be sure to plan as far in advance as you can to snag the best spots.
  5. These properties are located close to the beach or within walking distance to popular Key West attractions on Duval Street.

Here are the best Airbnbs in Key West, sorted by price from low to high.

Central-based studio one block from Duval, $147

Best Airbnbs in Key West - Central based studio one block from Duval, $147

Book this central studio starting from $147 per night

Located just one block from Duval Street, this studio apartment is an ideal base for a quick getaway. There’s also a private parking spot, which is a serious perk when visiting Key West as parking comes at a premium. 

This first-floor studio is small but well laid, with a Queen-size bed and a separate kitchen and dining area, complete with granite countertops. A large wooden wardrobe easily allows travelers to unpack and settle in. The unit is part of a historic building and though simple in decor, it has all the necessities and even boasts a deck with a small sitting area. Past guests rave about the property’s cleanliness and its proximity to many of Key West’s major attractions. 

Visit the famous Sloppy Joe’s Bar, opened in 1933, or the nearby Key West Butterfly Nature Conservatory. You’ll also find plenty of shopping and restaurants right nearby. 

This spot is popular, but has a few scattered dates open over the next few months.

Oceanfront studio on a private beach, $199

best airbnbs key west oceanfront studio

Book this oceanfront studio starting from $199 per night 

This second floor, oceanfront studio is a rare property in Key West at this price point, which means that bookings fill up quickly. The condo has a King-sized bed and a large balcony that overlooks the Atlantic ocean. As an added bonus, the home also includes access to the pool and hot tub on the property grounds, though these are shared amenities. 

Visitors will get the best of both worlds with the beach and nightlife right at their fingertips, as this condo is just a five-minute walk to Duval street. There’s also a free garage parking spot that comes with a unit. The studio sits on its own stretch of private beach, so guests can go for a swim or lay out on lounge chairs that are provided by the property. 

Inside there’s a collection of wood and wicker furniture and a plush armchair in soft, pastel tones. The bedroom has four plantation shutters that look out to views of the ocean and ample closet space to unpack. There’s also a small fridge and microwave at your disposal, though there isn’t a full kitchen. 

This listing books up well in advance. While there are a few scattered dates open over the next several months, you may want to consider booking a winter trip now. 

Sailing yacht, $224

Best Airbnbs in Key West - Three bedroom sailing yacht, $224

Book this sailing yacht starting from $224 per night 

One of most unique properties in Key West, this spacious yacht is ideal for adventurous travelers. Nicknamed “The Someday Soon”, the yacht features three sleeping areas with a setup that’s especially ideal for families, including a Queen size bed in the aft cabin, a Full-size bed in the midship, and two Twin beds in the forward cabin. 

The yacht is a vintage Mason boat with a mid-century modern interior that includes turquoise accents, carved wood trim, and polished wood floors. The eating area has a comfy breakfast nook and large windows that open up to let in the light. If you want to eat your meals on board, there’s a four-burner gas stove, an oven, and a refrigerator and freezer in addition to a grill on the deck. 

The full-size bathroom has a shower and lots of storage space under the sink. While the vessel is roomy inside, there’s also lots of seating outdoors. The cockpit is furnished with taupe and turquoise cushions and pillows, making it an ideal reading retreat.  

As an added option, the booking comes with a day sail, and the marina can provide a captain at an extra charge. Guests are also welcome to use the marina amenities like the heated pool and the gym. 

This boat has a few open dates in May and June, with more dates opening up starting in July.

Modern townhome right on Duval, $225

Best Airbnbs in Key West - Two bedroom townhome in the heart of Key West, $225

Book this modern townhome starting from $225 per night 

This large townhome puts guests at the heart of the action, thanks to its location right on Duval. Large spaces at this price point are hard to come by in Key West, so this property is a gem for families or larger groups. The inside has been recently renovated with calming neutral tones and standout features include two comfy couches with pops of colorful pillows and a round wooden dining table that seats five.  

There’s a parking spot included, although you probably won’t need your car during your stay since many of the most famous Key West restaurants, like DJ’s Clam Shack, are only feet away. 

The lower level of the townhomes includes an open floor plan with a kitchen, dining room, and full bathroom. Upstairs, the pitched roof makes the bedrooms extra cozy and there’s also a sitting nook. 

This home has some availability in May and June, but fully opens up starting in July.

Cozy cottage with a hot tub, $243

Best Airbnbs in Key West - Cozy cottage with a hot tub, $243

Book this cozy cottage with a hot tub starting from $243 per night 

A great property for families, this large cottage is loaded with rustic charm, from the wood paneling throughout the kitchen to the retro bathroom fixtures. Each bedroom is outfitted with a plus, King-sized bed, and the living room boasts a comfy sofa and side chair along with a dedicated workspace.

The home has a fenced backyard with a beautiful garden area. The outdoor oasis includes a private hot tub, a bamboo enclosed outdoor shower, and a patio dining set that seats four. 

It’s tough to beat the location, just one block from Duval street, and there’s a parking spot included. The cottage is also walking distance to Mallory Square, which is home to the best street entertainers and sunsets in Key West. If you’re a pet owner, you can bring your pooch to this dog-friendly property. 

This popular listing has limited availability over the next few months, but availability is subject to change.

Colorful condo steps from Duval, $250

Best Airbnbs in Key West - One bedroom condo steps from Duval, $250

Book this colorful condo starting from $250 per night 

The huge deck and central location make this condo in downtown Key West a prime choice. Aptly named Bella Vita, or “good life,” the property has a wrap-around porch with white Adirondack chairs for relaxing or some good old-fashioned people watching during downtime.  

The interiors are decorated in bright, cheery colors, including orange and turquoise walls, a red leather sofa, and blue accent pillows. The large master bedroom has a King-sized bed, a desk/vanity space, matching bedside tables, and a sound machine to enjoy a peaceful sleep. and the bathroom has an indulgent frameless glass walk-in shower. The galley-style kitchen includes bar seating at the kitchen counter. 

The ground-floor condo is also close to nearby bike and scooter rentals, so you can cruise around the island in style. 

This home has availability starting in July. It typically books well in advance, so it’s worth planning ahead and booking a late summer or even a fall or winter trip now.

Cheerful condo near Mallory Square, $280

Best Airbnbs in Key West - One bedroom condo near Mallory Square, $280

Book this cheerful condo starting from $280 per night 

With a large, shaded balcony overlooking the nearby cluster of Victorian-style homes and located within a quiet gated community in the Truman Annex, it’s no surprise that this listing gets a near-perfect rating. 

The inside of the condo is painted in bright yellows and blues, creating a sunny vibe that matches its location. The living area is found upstairs and includes plenty of seating options for lounging around, including a contemporary sofa lined with oversized pillows and a velvet armchair.   

The dining area seats up to five, and the kitchen was recently updated with white shaker cabinets and gray stone countertops. There’s a porthole above the kitchen sink that gives it a slight maritime theme, which continues with seascape art and a floor-to-ceiling bookcase filled with model ships and starfish. 

The historic Hemingway house, Maritime Museum, and Truman White House are all close by. The condo is also a short walk to Zachary Taylor Park, one of the top public beaches in Key West. Bike rentals are only a block away, and the condo includes bike storage for guests.

Currently, the owners require a 28-day rental commitment, though that may change in the coming months.  

Tropical Old Town bungalow close to the beach, $304

Tropical Old Town bungalow close to the beach, $304

Book this tropical bungalow starting from $304 per night

Step inside this breezy bungalow located in between Key West’s Art Gallery District and the Historic District, two pedestrian-friendly areas of Key West. 

The interior of the unit is bright and airy, decorated in complementary shades of coral, lime green, and blue. The main living area has an open floor plan and the kitchen has a two-tier island that overlooks the living room. Relax on the cream-colored couch that’s adorned with palm leaf printed pillows under a palm leaf fan to really get into beach mode. 

A matching palm leaf fan is found in the bedroom, which also boasts an elevated deck with a hot tub and high-top dining setup. Back inside, the bathroom has a spacious walk-in shower, and there’s a full-size washer/dryer in the hallway. 

There’s a shared courtyard space with a pool and a grill, and the property is also less than a mile from the beach, so after you settle in, you can make a beeline for the warm waters.

This home still has a few dates open in May and June, with more dates opening up in July and August.

Secluded hideaway with a private hot tub, $311

best Airbnbs in Key West - Secluded "mango" hideaway with a private deck, $311

Book this secluded hideaway starting from $311 per night

Tucked away in historic Old Town, this quaint cottage is great for those who want want to be close to the action on Duval Street (only half a block away), and who also value their privacy. 

The space is decorated in a tropical theme with green and turquoise linens and dark wood furniture. The kitchen features new cabinets, granite countertops, and full-sized stainless steel appliances. There’s also a deep brown leather sofa bed in the living room that’s within eyesight of the open-plan bedroom. Both the bedroom and the living room have large French doors that lead out to the deck, creating a relaxing indoor/outdoor setup when fully open. 

The spacious deck is the real selling point of this property, with a four-person jetted hot tub,  rattan patio seating, and a grill for making meals al fresco. The property even includes a large mango tree that has been lovingly preserved by being integrated into the design of the deck. 

There’s also a shared pool about a block away, and the cottage is within walking distance to the famed Cuban Coffee Queen and the free Duval shuttle bus. 

This home still has a few dates open in May and June, with more dates opening up in July and August.

Historic Key West suite in Old Town, $447

Best Airbnbs in Key West - Historic Key West suite in Old Town, $447

Book this historic Key West suite in Old Town starting from $447 per night 

Guests staying at this property get to experience a piece of Florida history. This suite is part of a property in Old Town that was built in 1889, and it’s only three blocks from Duval Street. 

Though technically a guesthouse suite, the first-floor accommodation has its own entrance and is entirely private. The kitchen has modern appliances, warm recessed lighting, and a dining area with an expandable table. In the sitting area, there’s a loveseat that can fold out into a bed and a folding screen that can be used to create a private sleeping space.

Outside, there’s an expansive deck and a wicker patio set with a coffee table and an ottoman, ideal for sipping coffee in the morning or cocktails in the afternoon. The grounds of the yellow guesthouse feel like a secret garden, with a brick path winding around the tropical landscaping to a pond. Guests can also access a pool that’s shared with other units. Past guests have described this listing as a “tropical paradise.”

This home still has a few dates open in April and May, with more availability in June and July.

More great Florida Airbnbs

Best Airbnbs in Miami - Tropical cottage in Biscayne Park near Bal Harbour, $100
Read the original article on Business Insider