Quirky Key West in the Florida Keys is famous for its free-spirited independence, gorgeous waterfront views, and fantastic revelries. That said, it’s more than just a party town, even though it might not look like it. And its many personalities are most evident in the diverse nature of its stays, whether it’s luxurious waterfront resorts or small boutique hotels. But what sets staying in Key West apart is the fact that, surprisingly, it has many B&Bs, too. We found so many options for the best bed and breakfast in Key West, Florida, that we were surprised there were none at all. However, we didn’t know that the Key was a place of settlers and pioneers, with many beds and breakfasts that had Cuban roots. In fact, many Spanish people arrived here and purchased properties, thus putting down roots.
So, whether you’re looking for a family vacation or a romantic getaway, Key West has a place for everyone. From the moment we arrived, we were awash with an instant wave of relaxation, which is the overall vibe of the B&B scene of the southernmost point in the continental United States. While it might be known for its tropical scenery, warm weather, and party scene, the Key has an inimitable bohemian streak that sets it apart from the rest of Florida. Here’s a comprehensive guide to the B&B scene in Key West, Florida.
Our Favorite Bed & Breakfast in Key West
- Key West Bed and Breakfast
- The Mermaid & The Alligator
- The Artist House
- The Conch House Heritage Inn
- The Garden House
- Ambrosia B&B
- Weatherstation Inn
- Simonton Court Historic Inn & Cottages
- Old Town Manor
- Westwinds Inn
- Southernmost Point Guest House & Garden Bar
Social Hubs
Key West’s Duval Street and the stays in and around it are a bustling hub of frenzied energy. Not only are they home to the best drinking, dining, and entertainment in the town, but they’re also home to B&Bs, where the focus is on mingling.
Key West Bed & Breakfast
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Within walking distance of Duval Street sits the amazing Key West Bed & Breakfast, tucked in a historic, 3-storied, late 19th-century mansion. We were within a stone’s throw of Duval Street’s action and Mallory Square and its sunset revelries. What’s more, there was a hot tub in the backyard, bicycles we could borrow, and a pool next door that we could use! Plus, the lush gardens were perfect for lounging around, and there were lots of common spaces with seating where we could meet our fellow guests and sit and mingle. That and the friendly ambiance here make it one of the liveliest B&Bs we’ve ever seen.
The Backstory And Hosts
Key West Bed and Breakfast’s ownership has changed quite a lot of hands, with it being originally owned by Jody Carlson, who ran the B&B with her general manager, Lizzy Macaskill. Together, they created quite a reputation for the B&B, tending to each guest as if they were family. Even after the Riley Hotel Group took over under the VP-ship of Lisa Zifer, the B&B hasn’t changed its overarching motto of incredibly personal guest service. The current general manager, Bella, is a fantastic hostess who tends to our every whim. Not only did she hook us up with bookings and recommendations, but she was so personable that we felt like we’d come back home, but only with a whole lot of comfort and amenities. She’d even bake special bread to accompany our breakfast selections, making our stay in this lovely B&B perfect.
Food And Drink
Every morning, a free hearty continental breakfast was served buffet-style on a blue-tiled antique table in the kitchen, where we could mingle with the other guests. It included tropical fruit, types of bread, homemade cakes, and even other specialties that Bella would whip up sometimes. There would be poached eggs and French toast on some days, but we’d find OJ and strong Cuban Queen coffee every day. Since this is Key West, breakfast started at 8:30 am and ended mid-morning.
“We love long breakfasts, and this B&B allowed us to do that, and them some!”
WOW Travel
The Rooms
With just 10 rooms, the B&B exuded an intimate vibe, and it felt like we were staying in someone’s luxurious home. Four rooms on the second floor shared two bathrooms, while the rest were spread out, spacious, and came with their own private bathrooms. Some second and third-floor rooms, including ours, even had a private sundeck that looked out over the stunning property. An interesting tidbit is that former owner Jody Carlson built the 13-ft-long headboard in the Bates Room!
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Southernmost Point Guest House & Garden Bar
The Southernmost Point Guest House & Garden Bar has a long, storied history. When E. H. Gato Sr. built this rambling Victorian structure in 1894, he moved the entire house across the street and rotated it because his porches weren’t getting sunlight! Today, this 13-room B&B has the best sea breeze and is the only home on the even side of the street to have an odd-numbered address since its original address is 1327 Duval Street!
In 2020, they added the garden bar, which complements the surrounding tropical foliage with exotic orchids, mature palms, and hammocks sprinkled in between. The standout amenity was the all-ages outdoor heated pool, complete with beach chairs, sun loungers, and beach/pool towels graciously provided by the staff.
- Meet the hosts: The Santiago family has owned the B&B since 1987. It’s now managed by Mona Santiago and her family, who are very gracious hosts and stay on the property.
- Food and drink: Every morning began with a complimentary hot continental breakfast, which included everything from the likes of different types of breads and tropical fruit to oatmeal and eggs. When the weather was nice, we could even enjoy breakfast alfresco in the garden. The garden bar was a fantastic place to enjoy a cold one while also talking to other guests. However, Sandy’s food truck with the most delicious tacos ever was our favorite!
- Room type(s): 13 spacious rooms have private bathrooms, mini-fridges, microwaves, kettles, and cable TVs. While some had access to a shared wraparound porch, most of the others had private porches with partial views of the ocean, the pool area, or the gardens.
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Westwinds Inn
The elegant Westwinds Inn, sitting in a sweeping Victorian-style wood structure, took our breath away. But what we loved was the enviable location—it was a short walk from Duval Street and two blocks from the waterfront! So, if there was ever a place to stay in the middle of the bustle, this would be it. That is ironic, given that the hallmarks of the inn are relaxation and hospitality, which we absolutely reveled in. That was evident from the two swimming pools on the property, with a palm-lined courtyard to boot, all ours for lounging. In fact, one even had a jet spa that was heated for the winter months, which was perfect for when we visited!
- Meet the hosts: The B&B is managed by a very well-trained and warm team led by Victor, the Manager. They took care of all our whims, including dietary requests, and made our stay as comfortable as it was memorable.
- Food and drink: Our mornings here began with a hearty complimentary breakfast served by the pool from 8 to 10 a.m. every day, come rain or shine. It included OJ, coffee from the local roaster, Doing Work Coffee, hard-boiled eggs, yogurt, English muffins, bagels, and cereal.
- Room type(s): Even with 26 cozy rooms and suites, the inn offered all the intimacy of a B&B, especially since they all came with private baths. What’s more, the breezy rooms felt perfectly coastal, especially with the cane furniture and pastel hues. Our room boasted French doors that opened out onto a very spacious balcony.
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Romantic Stays
It might not look like it, but Key West is a very romantic destination, and the proof is in the form of the many romantic hotels in Key West. But that’s not all. History and modern amenities come together to form most of Key West’s romantic stays, where the amour goes back more than a few decades!
Old Town Manor
Formerly Eaton Lodge, Old Town Manor is a Victorian B&B in Key West’s Historic District. Since it was first built, the structure has been a butcher/grocery shop, a residence with a doctor’s office, and a boardinghouse. Today, it retains the original cypress door and the lush private gardens, one of Enter one of Key West’s oldest and loveliest. It has century-old palms, fish pond fountains, and even a Brazilian jacaranda tree with lovely blue bell-shaped flowers. If this doesn’t inspire romance, we don’t know what will.
- Meet the hosts: Jen and Jeff Zerby, Jr. currently own and run the B&B with the help of a wonderful team. Alison, Athena, and Haytham are at the front end, along with Katie and Kelly. Not only were they all wonderfully helpful, but they made our stay very comfortable.
- Food and drink: The deluxe continental breakfast here is a relaxed affair in the B&B’s sun-speckled tropical gardens from 8 to 10 a.m. We’d sip on strong coffee while helping ourselves to cheese, pastries, smoked salmon, waffles, and more. The best bit is that they even offer vegan, gluten-free, and organic choices every day. Check out their breakfast spread and details.
- Room type(s): We had the choice of 14 rooms, 10 in the main house and 4 rooms in the converted carriage house. What’s more, they all boasted private bathrooms with William Roam bath products, plush cloud-like beds, A/C, and flatscreen TVs. Some, like our room, even had furnished balconies to soak in the Key West vibe while enjoying coffee or wine. That, along with keyless entry and free Wi-Fi, made it a top favorite stay with us.
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The Garden House
The Garden House is an intimate, island-style B&B nestled on a quiet, tree-lined street in historic Old Town. We loved the warm, romantic vibes of this lovely B&B, which had two temperature-controlled pools set amidst sprawling tropical gardens, all ensconced in a sea of calm and tranquility – romance done right.
- Meet the hosts: While John Flynn owns Garden House, Sammy and Sandy are the amazing hosts at this guesthouse. Not only were they super-welcoming, but they also gave us some excellent recommendations for local things to do and food to eat. Moreover, Sammy ensured that we had everything we needed and were taken care of. However, the best person on the team was Katie, the resident “house manager”/pup!
- Food and drink: Breakfast was served in the dedicated breakfast room every day. Even though it was small, we loved getting down in the morning to dig into the delectable spread that Sammy would whip up. Think coffee, sweet rolls, parfaits, and waffles, among other things.
- Room type(s): Between the private marble bathrooms, the polished oak floors, and the sleek furniture, the rooms were real high-class affairs. Not only did they all have private entrances, but they also ranged from smaller rooms to larger ones. Our cozy king room even had a French door leading to a private patio that overlooked the gardens.
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The Conch House Heritage Inn
The Conch House Heritage Inn is the best bed and breakfast in Key West, Florida, and it’s easy to see why. It’s one of the few B&Bs with a lovely outdoor pool and daybeds where we’d swim and lounge to our heart’s content. With tropical scenery and drinks by the pool, there was no better place for romance.
- Meet the hosts: We were fascinated to find out that the innkeepers of Conch House were direct descendants of the original pioneers and settlers of Key West! It was once owned by grocer Carlos Recio, who is current owner Sam Holland’s great-great-grandfather, and the legacy continues even today. The team and staff, including Hillary, Carol, and Rebecca, were very warm, welcoming, and incredibly helpful with suggestions for things to see and do.
- Food and drink: Breakfast was served every morning from 8 to 10 a.m. by the pool, and trust us when we say that we’ve never had a better breakfast experience. It started out with a cup of local roaster Baby’s Coffee, followed by Lala’s world-famous homemade banana bread. It was followed by different quiches every day, baked goodies, cereal, fresh fruit, yogurt, tea, and freshly squeezed OJ. The cherry on top? Delicious champagne mimosas on top of everything.
- Room type(s): We had the choice of 10 rooms and suites, all of which were sleek yet cozy. They had plush beds, flatscreen TVs, and private bathrooms with complimentary bath products and bathrobes. We loved our Delaney Suite, the best room in the house. Besides a full kitchen, the ground-floor suite also had French doors leading to a rear porch with garden views, a barbeque, and comfy seating.
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The Mermaid & The Alligator
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The Mermaid & The Alligator is one of the most romantic hotels in the Florida Keys. Tucked in a charming 1904 Victorian mansion, it’s perfect for romance in Old Town. The lush surrounding vegetation makes it all the more romantic, with the eponymous statue of a lovely mermaid kissing the snout of the alligator right by the pool.
- Meet the hosts: Currently, the Riley Hotel Group, under the VP/ownership of Lisa Zifer, operates the B&B with a very efficient staff. Diana, the innkeeper, and the staff were very friendly and thoughtful and took care of all our needs.
- Food and drink: Every morning, freshly brewed coffee and tea are available at 7 a.m., followed by complimentary breakfast at 8:30 a.m. in the garden. Daily choices included fruit juices, coffee, boiled eggs, yogurt, cereals, muffins, toast, bagels, and a different hot entree every day. Think cinnamon French toast, Belgian waffles, breakfast sandwiches, made-to-order eggs, and avocado toast. Moreover, there’s Happy Hour with complimentary white/red wine and light snacks every evening from 4-5 pm. Finally, various coffees, citrus and sparkling water, and iced tea are available all day long.
- Room type(s): The Caribbean colonial-inspired rooms with French doors were perfect for a sensual, romantic getaway. Plus, the rooms downstairs, which opened onto the deck, the pool, and the gardens. We could even call for a couple’s massage in our rooms. Plus, we loved the special romance packages on offer, complete with Belgian chocolates, champagne, and whatnot!
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Historic Stays
With such a rich and storied history, it’s not exactly surprising that Key West is full of historic properties. In fact, many of the above-mentioned stays are all as historic as they get, going back not just years but more than a few decades.
The Artist House
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The Artist House is one of the Key West’s most photographed guesthouses. It’s Robert Eugene Otto and his prominent Key West family’s former home. In 1904, a young Bahamian girl gave him a fabric-made, straw-stuffed life-sized doll. He gave the doll his name, keeping it in his attic room. Eventually, it took the blame for everything negative in Otto’s life. When he returned to the house with his bride, the eclectic Otto often painted in the Turret Suite, with Robert the doll always propped up in the southwest window. Today, the doll resides at the Martello Museum, with only its spooky legend remaining in its place.
- Meet the hosts: Lori and Jason Barnett are the owners/innkeepers of the Artist House. Aiding them in the hopsitaly here are general manager/innkeepers Jessica and Shawn. We got to meet Normal, Mr. Pickles, and Clarice, some of the greatest, cutest pugs we’ve ever seen.
- Food and drink: Every morning from 8:30 to 10 a.m., they served a hearty breakfast in the tranquil orchid garden, the verandah, or our room. Think delicious items like bacon, pancakes, tacos, quiches, and Cuban breakfast sandwiches, along with organic yogurt, cheeses, pastries, bread, fruit salad, and hot and cold cereals. There was also an assortment of freshly squeezed OJ, milk, coffees, and breakfast teas, along with mimosas!
- Room type(s): The beautifully restored Victorian-era home boasts a vibrant exterior and elegant furnishings. All three rooms and four suites have vintage glam private bathrooms. Some have deep-soaking bathtubs, while others have vintage full-length mirrors. The Turret Suite is a two-story historical haven with a sleigh bed, two porches, and seven spectacularly tall windows.
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Simonton Court Historic Inn & Cottages
The adults-only Simonton Court Historic Inn & Cottages is a serene hideaway on a quiet side street in the heart of Key West’s Old Town. Formerly a cigar factory, it was where artisans hand-rolled some of the most famous cigars in the world. In fact, 1880-built historic cottages were the cigar factory workers’ homes, which line the brick walkway that was once a lane. Today, this gorgeous footpath is surrounded by luxuriant and verdant gardens, palm fronds, flowering vines, and gently swaying palms, along with four shimmering pools open 24/7.
- Meet the hosts: The B&B is a Moloney Smith project headed by lead designer Susan Moloney. Currently, the owner is artist Sue Clay Moloney, and her able team, led by Fabian, manages the B&B.
- Food and drink: Breakfast was served by the pool from 8:30 to 10:30 a.m., and the staff even readied breakfast bags when we had to leave early for a tour. For an additional USD 5, we could have a prosecco, a Bloody Mary, or a mimosa. For a USD 20 service charge, the staff would even serve us breakfast in bed. There were also fun meet-&-greets every Friday-Saturday with USD 5 drinks and complimentary snacks from 4–6 pm. When we’d lounge by the pool, we could order snacks and beverages from 11 am-4 pm. Finally, we could also order room service.
- Room type(s): With 30 rooms, this might just be the largest best B&B in Key West, FL. There are six rooms in the Mansion, four in the Townhouse, nine in the Historic Inn, two in the Manor House, and nine Cottages. Nevertheless, all rooms and suites boast TVs, fridges, private ensuite bathrooms, and patios that look out to the lush greenery.
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Weatherstation Inn
How would you like to live in a former weather station? Behold the historic Weatherstation Inn, a charming B&B on the grounds of a navy yard in Key West. The Navy has been around in Key West since the 1930s, with the establishment of the United States Weather Bureau building and a Navy submarine base at Truman Annex. The Weatherstation Inn building was the residence of the U.S. Navy after 1951, being abandoned after the base annex closed in 1974. Today, the two-storied Renaissance structure is surrounded by lush gardens, with a shimmering pool in the middle serving as its crown jewel.
- Meet the hosts: Our host, Donny, was as gracious as he was informative and told us all about the best things to do and see around. He was extremely thoughtful and took care of even our smallest needs, like when we wanted wine glasses on request. His pleasant concern for our welfare was delightful.
- Food and drink: We’d have a complimentary continental buffet-style breakfast laid out in the lobby every morning. It always included an assortment of Tazo teas, coffee from local roaster Baby’s Coffee, breakfast bars, whole fruit, yogurt, cinnamon rolls, and fresh croissants.
- Room type(s): With just eight rooms, staying here felt intimate and exclusive, with four rooms each on the first and second floors. Moreover, they all were decked out in soothing pastel hues, classic Key West shutters, plush beds, including a four-poster one, and other vintage furniture. The best bit? They all have private bathrooms.
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Family-Friendly Stays
It’s rare to find B&Bs that are family-friendly and allow children, but Key West isn’t one of those places. It had lots of places that welcomed kids under 16 and were no less comfortable than any of the other B&Bs in the area.
Ambrosia B&B
We were looking for family-friendly B&Bs in Key West, and Ambrosia B&B was perfectly luxurious and even welcomed children. This place was all about a casual atmosphere, personal attention, and a dollop of style, but what we all, especially the kids, loved was the themed rooms. Moreover, this delightful two-inn hideaway boasted lush grounds featuring outdoor tables, lounge chairs, a whirlpool spa, and not one but three pools! If you’re worried about keeping kids occupied, look no further.
- Meet the hosts: The Riley Hotel Group, under the VP/ownership of Lisa Zifer, owns and operates the B&B with a wonderful staff headed by Lee. He was not just super nice and chatty but also helpful. He even gave us extra towels for the kids when we went down to the pool!
- Food and drink: Breakfast was a do-it-yourself buffet affair served in the little garden gazebo by the pool from 8:30 to 10:00 a.m. Thankfully, coffee was available earlier, so we enjoyed a quiet cup of joe on our patio before the kids woke up. The buffet had everything delicious, as well as stuff to keep the kids interested, like muffins, strawberry banana yogurt, bread, and OJ.
- Room type(s): The rooms offered are themed rooms, like the Havana Cabana, Sailfish Suite, and Treetop, all with private entrances to gardens and verandahs. Since we were traveling with two kids, we chose the two-bedroom, two-storied Katie’s Kottage. It even had a full kitchen so we could whip up meals for the children at any time. The best bit? French doors opened onto a deck, which had a dip pool! Moreover, all rooms boast porches, spacious bathrooms, and wood/wicker furniture.
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Where to Stay in Key West?
Key West boasts a unique geography, sitting at the end of the Florida Keys, where the Gulf of Mexico meets the Atlantic Ocean. So, where should one stay here? For first-timers, we’d highly recommend staying in the Duval Street area. This vibrant neighborhood is home to the city’s most famous street and is home to many local shops, restaurants, cafes, and bars. However, as we wanted to explore the B&B scene, we stayed in the enchanting Old Town, which was home to many vibrant, 1800s-built structures and radiated an off-the-grid vibe. There’s a B&B on practically every corner, as well as museums, art galleries, and buildings full of history. If there was ever the perfect personification of Key West’s B&B scene, it would be Old Town. It has a slew of options for the bed and breakfast in Key West, Florida.
Besides the B&B scene, the historic Seaport area is ideal if you want to indulge in water adventures. This neighborhood has plenty of fun water activities, including cruises and picturesque ocean views. Finally, live like a local in Bahama Village, which lies in the southern part of Key West.
You might also want to check out the best hotels in Key West.
Is it better to stay in Old Town or New Town for the B&B scene in Key West?
The Historic District, a.k.a. Old Town, is where you should stay for all sorts of charming bed-and-breakfast experiences.
What is the history behind Key West?
Ponce de Leon discovered Cayo Hueso (Island of Bones), as Key West was called, which was consequently claimed by Spain in 1813 and named Las Martines. 4 centuries later, Don Juan de Estrada granted it to Juan Pablo Salas in 1815 for meritorious service to the crown. Finally, Alabamian John W. Simonton bought it from Salas in 1821 for USD 2,000. Consequently, settlers arrived, making them the descendants of the residents of Key West today.
Why are Key West accommodations so expensive?
Since the Key is a small island with limited space, there’s more demand and less supply, driving up the prices, especially during peak tourist seasons.