Last Updated on July 4, 2024 by Marybeth
There may be few ‘best-kept secret’ lodgings in Key West anymore, but there will always be hidden gems.
With five million visitors a year on this seven square mile island, how can anything be a secret? But we’ve found a hidden gem – an oasis, really – you may not know about: Winslow’s Bungalows.
Winslow’s Bungalows, Est. 1856, is part of Key West Historic Inns’ collection of five quintessentially Key West hideaways filled with character and island-chic décor, each with a unique vibe. From smaller properties – each with its own swimming pool, two with poolside bars – to the largest (Winslow’s Bungalows), choose from two Adult-Exclusive inns, or bring the whole family to the other three. Winslow’s Bungalows would be our choice for families with kids: those three swimming pools!
All guests of Key West Historic Inns are welcome to enjoy all the Inns’ pools, bars, guest gathering areas, complimentary breakfasts, and Merlin’s Afternoon Teatime hosted at Ella’s Cottages.
Key West has a long history of offering travelers a chance to get away from it all. The earliest documentation we found for a vacation home is in 1946 when President Harry Truman’s doctor ordered him to “take a warm vacation.” A cure way better than meds!
Truman stayed in an officer’s quarters cottage that was built in 1890, calling it The Little White House. His thinking was that where the president was, the White House was. Documents from The Little White House read, “The White House, US Naval Station, Key West.” There is a way around everything! Especially when you’re the president, under doctor’s orders.
You may be thinking “From early on, Key West built a slew of Inns that are now historic. What makes yours special??”
Come along and we’ll show you!
The Grounds
Winslow’s Bungalows may be the most spacious campus of the Inns’ collection, but you’ll get a feeling of privacy and peace as you explore the winding brick walkways. The calming aesthetic wraps itself around you with swaying palms, vibrant tropical flowers, and multiple outdoor areas to while away an afternoon.
You’ll feel truly hidden, far from the fray and the dynamic activity on the more popular Key West streets. But they are within an easy stroll. The best of both Key West worlds!
The outdoor spaces at Winslow’s Bungalows might just be what you’ll love best about this enchanting Inn. Spread out over acreage that was once a fruit grove, these well-kept tropical gardens offer multiple spots to just chill, alone or with family and friends.
The Swimming Pools
The largest swimming pool is just outside the stately historic former home that is now Winslow’s Bungalows’ lobby, which makes it easy to find. Take a nearby curving pathway, turn left (there are directional signs inlaid in the pathways, thankfully: you won’t get lost) and you’ll eventually come upon swimming pool number two. This swimming pool has a more intimate feel, is within steps of The Bungalow Bar (stellar location!) and the rooftop hangout, pictured above.
We were so delighted by the swimming pool just outside of our Bungalow, we didn’t make it to swimming pool number three. Check it out and let us know how you like it!
The Bungalow Bar
The Bungalow Bar drew us in with its low-key welcome, comfy spots to sit for Happy Hour, breakfast, and lunch, and most of all the gracious hospitality of the bartender, Keith, and Winslow’s Bungalows’ chef, Michael.
Upon arrival you’ll receive a Pirate’s booty-looking token to redeem your Welcome Drinks. The lovely gentleman who checked us in and gave us a tour of the grounds and our suite offered to order our drinks and bring them to our room! Such a luxurious-feeling offer, but you’ll want to sit yourself barside. Not only will you meet fellow travelers of like minds, you’ll enjoy hearing Keith’s retelling of some of the fabled history of Winslow’s (nefarious things may have happened here long ago!)
Some of the more tame tales are this was once a vaudeville venue and home to a circus performer. Ask Keith about the original Inn: The Red Rooster Inn. And the Cigar Man. Dugouts hiding pirate loot. There might have been a murder. Have there been ghost sightings?… I’m not saying there have been. But I’m not not saying it.
Keith will mesmerize you with his mixologist skills: ask him to concoct one of his signature cocktails. He’ll explain the origin of your drink and its name, and bring out each bottle and tell you all the ingredients, and why they make such a great cocktail. You’ll have the inside scoop to continue this vacation vibe at home!
Keith is a 24-year local, or what old timers here call a ‘fresh water conch.’ “I’ve been a chef, waiter, manager, and after the shutdown I chose my dream retirement job: pool bartender.” Keith’s favorite drink to make is a Mai Tai, and variations of it. “Almost anything with rum.”
Breakfast & Lunch at Winslow’s Bungalows
As a guest your complimentary breakfast at Winslow’s Bungalows will be a highlight of your whole trip. The high standards of Chef Michael are evident in the variety of the offerings, and in the delicious house-made hot menu items each morning. Your choices will vary – one morning we indulged in blueberry and strawberry pancakes. Freshly cooked waffles appeared the next morning, along with made-fresh-daily bagels, pastries, muffins, and croissants.
Chocolate croissants, Nutella Beignets, and bread pudding were a few of the specialties during our visit. You’ll find healthy options as well: freshly squeezed juices, smoothies, fresh fruit, wellness shots of citrus, ginger, turmeric, and cayenne, various flavors of lowfat yogurt with fruit toppings, a platter of sliced meats and cheeses, and secret-ingredient deviled eggs. (I wrangled the secret out of Chef Michael, DM us on Instagram and I’ll give it away!)
You can request a made-to-order breakfast as well. For $15 Chef Michael will make a Sausage, or Bacon, Egg and Cheese Breakfast Sandwich, or an Omelet with Cheese, Veggies, and Meat.
After breakfast, and a busy morning exploring Key West, we were happy to settle ourselves right back at our poolside / barside table for lunch! Chef Michael turns right around after that epic breakfast and is happily creating his delectable lunch.
We had a chance to talk with Chef Michael when mealtimes quieted down, and enjoyed hearing how he modestly described his craft. With thirty+ years in the business, and despite rave reviews, Michael said “I never consider myself the best. I just make fresh, flavorful, homestyle food. The stuff people love to eat. Occasionally I might get carried away.” Visiting Key West some years ago, he decided to stay. “I love Key West, everything about it. It’s such an easy, comfortable place to be.”
The Bungalows!
It’s taken me this long to get to the most important part? And I swear we didn’t choose this place because of the name. But, BUNGALOWS. You have to admit, it has that intriguing, yet restful ring to it.
At Winslow’s Bungalows – and at all the Key West Historic Inns’ properties – you’ll find a variety of room sizes and styles to suit your travel needs and budget. From cozy and intimate, to larger rooms and suites, many offer outdoor spaces where you’ll have your own patio or balcony. Peruse the room choices, here, where each room type lists its square footage and outdoor space options.
The Bungalow for our visit was the Treehouse Suite.
The calming, luxurious energy, space to spread out, and the visually pleasing use of art and color in the Treehouse Suite had us wanting to hunker down and never venture out. You’ll see why:
But we DID venture out, and not just to The Bungalow Bar! Of course we did the tourist thing, and enjoyed the heck out of ambling down Duval Street. We stopped into a few of the famous bars, sitting shoulder-to-shoulder with other tourists and not minding at all that fellow-feeling of doing the expected thing. We like to call ourselves travelers, but in Key West, all that goes out the window and we’re proud to be plain old tourists. Key West does that to a person, and isn’t that a beautiful thing?
We recommend that you venture out to Merlin’s Afternoon Tea at Ella’s Cottages during your stay.
Merlin’s Afternoon Tea at Ella’s Cottages
When we first heard “Afternoon tea” we weren’t leaping to pull on our dressy clothes (does anyone bring dressy clothes to Key West?) Would I need to wear a hat? We don’t even really like tea.
When I asked the gentleman at the front desk if we needed to dress up for tea I could sense he was fighting back (gentle, and kind, I’m sure) laughter. “No one dresses up in Key West! In fact, you are overdressed right now, to be honest. I hope you don’t mind my saying so.”
If we’d stayed home because we don’t like tea (swanning around our Treehouse Suite in our Turkish robes) we’d have missed one of the most fun little adventures of our stay with Key West Historic Inns! Merlin’s Afternoon Tea is not your great-grandmother’s tea, nor is it any facsimile of the Queen’s afternoon tea. No offense to Her Majesty.
Ella’s Cottages may look classic and understated from the outside, but her lobby, and her guest gathering room, are stylish, modern, and a little bit boho. The pretty pink and peach tones of the crockery (is that a grandma teatime term?) contemporary wall tiles, fun nods to straw hats in the zhuzhed-up hanging pendants, and that retro little fridge made us smile, and the dainty little snacks did, too. Neat mini pastries and crustless tea sandwiches, smoked salmon-topped crostinis, house-made iced tea, and canned cocktails – yes, cocktails – made our afternoon. We thoroughly enjoyed our Two Chicks Sparkling Paloma, and Sparkling Citrus Margarita.
Remarkable Restaurants Just Around the Corner
Key West brims with so many options for dining out, your head will spin. You can opt to just stay in your neighborhood. We found three culinary gems (somewhat hidden!) a short walk from Winslow’s Bungalows.
Just three minutes away, tucked into and surrounded by small Conch style cottages, is Little Pearl Key West. A tasting menu restaurant, with four courses (3 options per course) plus some add-ons; be sure to make a reservation for this exquisite experience. Not your typical fried fish basket with a blender margarita type stop. Instead, expect innovative cuisine with tropical notes, crafted with creativity. Perfect spot for a special-occasion meal. That special occasion could be just because you’re in Key West and are looking for a memorable evening!
Another three minute walk, slightly northeast on Truman Avenue, you’ll find Seven Fish. Cheerful bistro-style interior with a seafood-forward menu, Seven Fish’s signature dish is their Yellowtail Snapper Curry. We’ve heard the locals’ favorite is the meatloaf, and you’ll find chicken and steak entrees as well.
El Siboney is our third recommendation for outstanding food in your neighborhood during your stay at Winslow’s Bungalows (a six minute walk, this time.) Known to be Key West’s best restaurant for authentic Cuban food, the menu is extensive and everyone raves about the sangria.
Key West Historic Inns
We won’t stop talking about Winslow’s Bungalows for quite awhile (ever?) and the extraordinary hospitality we encountered at every turn from the staff at Key West Historic Inns. Each of the five Inns has a story to tell, and a warm welcome for everyone.
Ridley House, Est. 1884. For Honeymoons and VIP Vacays.
Winslow’s Bungalows, Est. 1856. For Every Key West Escape.
Lighthouse Hotel, Est. 1858. For a Lively Social Scene.
Ella’s Cottages, Est. 1948. For Groups and Longer Stays.
Fitch Lodge, Est. 1892. For On-the-Go Explorers.
Follow Key West Historic Inns on Instagram and on Facebook.
Our stay at Winslow’s Bungalows was hosted, and as always, our opinions are our own.
