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Winslow's Bungalows
Lively. Social. Effortless CONNECTION.
Winslow’s Bungalows offers a vibrant escape where colorful history, lush gardens, and relaxed island living come together. Perfectly positioned within walking distance of many of Key West’s favorite shops, restaurants, and attractions, it places the best of the island just moments away. Three pools, welcoming outdoor spaces, live music, and daily experiences create a setting that’s equally suited for lively afternoons with new friends or peaceful moments to unwind.
stay with us
Inviting rooms pair historic Key West character with an easy, comfortable style. Many feature a deck or outdoor seating, offering your own space to slow down and make yourself at home between adventures.
Traveling Together? Stay Together.
Explore Elizabeth Estate
Eat + drink
Bungalow Bar
Restaurant and Bar
Welcoming hotel guests, locals, and visitors to gather over great food and good company. A favorite for poolside lunches and afternoon cocktails, it’s known for signature Rum Runners, frozen drinks, the Mahi Tostada, and the Bungalow Burger. Pull up a chair, order another round, and enjoy the easygoing atmosphere that makes The Bungalow Bar one of the neighborhood’s favorite places to meet.
Three Ways to Poolside
Find your favorite lounger, cool off with a refreshing dip, or gather with friends between adventures. Order a cocktail and a poolside snack from Bungalow Bar, soak up the Key West sunshine, and stay awhile.
Amenities at Winslow's
Three pools, live music, poolside dining, welcome cocktails, daily happy hour, and thoughtfully curated experiences make Winslow’s Bungalows the heart of the collection.
Complimentary Breakfast
Mornings begin at The Bungalow Bar with a complimentary continental breakfast served daily from 8:00 AM to 10:00 AM.
Live Music
Good music has a way of bringing people together. View our Live Music Schedule to see who’s playing during your stay.
Welcome Cocktails
Redeem your Pirate Loot coins for two welcome cocktails at Bungalow Bar, daily from 8 AM–8 PM.
Parking Made Easy
On-site parking is available for an additional nightly fee, keeping your car close throughout your stay.
Personalized Experiences
Make your Key West stay your own. From in-room extras and dinner reservations to island experiences, our concierge team can take care of the details.
Part of Your Stay
Enjoy Wi-Fi, filtered water, coffee, and tea throughout your stay, plus yoga mats, live music, and entertainment for a little more Key West.
Bicycle Rentals
Explore Key West your way with on-property bike, e-bike, scooter, and golf cart rentals from Island Safari Rentals.
Better Together
Bring the whole crew. From milestone celebrations and wedding weekends to reunions and getaways with friends, Winslow’s gives groups room to stay, gather, and make a weekend of it.
A Social Butterfly One Day Itinerary
Key West is better with good company and a little spontaneity. We’ve gathered a few of our favorite places to sip, mingle, linger, and see where the day takes you. Consider this your invitation to get out there and make a few stories of your own.
Stay inspired,
The Winslow’s Bungalows Innkeepers
Breakfast at Bungalow Bar
8:30 am
Ease into the morning over breakfast at Bungalow Bar. Grab a table, have another coffee, and don’t be surprised if a conversation with the people next to you changes the plans for the day.
Explore on Two Wheels
10:30 am
Pick up a bike at Winslow’s and head into Old Town. The fun is in the stops, the side streets, and the people you meet between wherever you thought you were going and where you actually end up.
Wander, Shop & Stop
12:30 pm
Browse the boutiques, galleries, and only-in-Key-West shops along Duval and beyond. Pop in wherever catches your eye, stop for a drink, and leave a little room for whoever or whatever you find along the way.
Lunch at Blue Heaven
2:00 pm
Grab a table at Blue Heaven, one of Key West’s most iconic gathering spots. Live music, colorful characters, cold drinks, and a lively courtyard make lunch feel like part of the adventure.
Sunset at Mallory Square
Dusk
Key West sunset is less something you watch and more something you join. Street performers, musicians, locals, visitors, and plenty of characters gather nightly for one of the island’s longest-running social traditions.
Eat Like a Local
8:00pm
Grab a table at El Siboney, order a few Cuban favorites to share, and settle in over good food, cold drinks, and even better conversation. It’s a longtime Key West favorite and the perfect start to a night out.
Duval After Dark
10:00 pm
Follow the music, find a lively bar, and let the night take it from there. Make new friends, stay for one more, and enjoy Duval after dark. Winslow’s is just a block away when you’re ready to call it a night.
Inspired by Key West, Named for an Artist
Named for renowned American painter Winslow Homer, who found inspiration in Key West, Winslow’s Bungalows carries more than a century of island stories within its historic grounds.
” Winslow’s feels intimate, more like a collection of private homes than a conventional hotel. ” -Condé Nast traveler
Exclusive Offers
See What's Happening
There’s always something happening in Key West. Explore our calendar for live music and events at the inns, plus festivals, celebrations, and island favorites happening around town during your stay.
Paradise, Poured
Cypress Sangria
Mallory Square Sunset
A nightly Key West tradition of sunsets and waterfront entertainment.
🌴 Mallory Square
- 4:00 PM to 7:00 PM
Happy Hour
A daily Key West tradition.
🌴 Bungalow Bar at Winslow's Bungalows
🌴 Isabel's at Lighthouse Hotel- 4:00 PM to 6:00 PM
Sam Carlson
Wine Down Wednesday
Throwback Thursday
Farmer’s Market
Shop local produce, artisan foods, and handmade goods.
🌴Truman Waterfront Park
- 1:00 PM to 6:00 PM
Jamie Sellers
Sam Carlson
Flocktail Friday
Fantasy Fest
A legendary celebration of Musical Icons & Iconic Musicals.
🌴 Various Locations in Key West
- All Day
Martin Sedlak
Wavy Davy
Toko Irie
Nina Newton
Goombay Festival
Celebrate Bahamian culture, music, and island flavors at Goombay Festival.
🌴 Bahama Village
- All Day
Martin Sedlak
Key West Artisan Market
Rum, Lime, and Sunshine
Buy One, Get One Margaritas & Mojitos
🌴 Bungalow Bar at Winslow’s Bungalows
🌴 Isabel’s at Lighthouse Hotel- 2:00 PM to 4:00 PM
Greatest Hits Pool Party
Greatest Hits Pool Party takes center stage during Fantasy Fest.
🌴 Winslow's Bungalows
- 12:00 PM to 4:00 PM
Aaron Luka
Gi & Rolando
Trop Rock’N Duval
Trop Rock’N Duval
Trop Rock’N Duval
Live music and poolside fun with Reggie Starrett.
🌴 Winslow's Bungalows
- 2:00 PM to 5:00 PM
Wichita Jack
Nina Newton
Trop Rock’N Duval
Live music and poolside fun with Dave Freeman & Friends.
🌴 Lighthouse Hotel
- 4:00 PM to 7:00 PM
Drag Me To Lighthouse
World’s Fastest Boat Parade
The excitement of offshore racing brought to the heart of Old Town.
🌴 Duval Street
- 4:00 PM to 5:00 PM
Race World Offshore World Championship
Bringing the world's fastest offshore powerboats to the Key West waters,
🌴 Various Locations in Key West
- All Day
Holiday Boat Parade
Beautifully decorated boats illuminate the Historic Seaport.
🌴 Historic Seaport
- 6:00 PM to 12:00 AM
Literary Seminar
Celebrate Key West’s literary legacy with acclaimed authors.
🌴Various Locations in Key West.
- All Day
Half Marathon & Runfest
Four races and a full weekend of island celebrations.
🌴Various Locations in Key West
- All Day
Mile 0 Fest
Five days of Red Dirt, Americana, sunshine, and island energy.
🌴Various Locations in Key West
- All Day
Food & Wine Festival
Five continents, incredible wines, and celebrated chefs.
🌴 Various Locations in Key West
- All Day
Seafood Festival
Conch Republic Independence Celebration
Dine & Drink
- 801 Bourbon Bar
- Aqua Bar and Nightclub
- B.O.’s Fish Wagon
- Bagatelle
- Better Than Sex
- Blue Heaven
- Boat House Bar & Grill
- Dante’s Pool Bar & Restaurant
- Green Parrot Bar
- Greene Street Cigar Company
- Half Shell Raw Bar
- Kermit’s Key West Lime Shoppe
- Key West First Legal Rum Distillery
- La Crêperie
- Little Pearl
- Lola’s Bistro
- Mangia Mangia Pasta Cafe
- Moondog Café
- Nine One Five Restaurant & Bar
- Old Town Bakery
- Onlywood Grill
- Papa’s Pilar Rum Distillery
- Pepe’s Cafe & Steakhouse
- Santiago’s Bodega
- Sarabeth’s in Key West
- Seven Fish
- Sinz Burritos Key West
- The Waterfront Brewery
- Vinos
- ViV Wine Bistro
Arts & Entertainment
22&Co
This vibrant, inclusive and creative bar offers tons of local charm to go along with happy hours, fresh cocktails, fun bartenders and weekly drag shows.
801 Bourbon Bar
Head to this lively LGBTQ+ venue on Duval Street for its energetic atmosphere, entertaining drag shows and diverse cocktail offerings.
Alan S. Maltz Gallery
Immerse yourself in Key West’s vibrant entertainment scene at the newly renovated Key West Theater, just a 3-minute stroll from Ridley House, offering the best in comedy, concerts, and live performances.
Aqua Bar and Nightclub
Known for its energetic drag shows, inventive cocktails and upbeat atmosphere, Aqua Bar is a popular destination for those seeking a memorable night out in Key West.
B.O.’s Fish Wagon
Offbeat, eclectic and undeniably delicious. B.O.’s Fish Wagon, just a 3-minute walk from Ridley House, delivers big on fresh flavor and Key West vibes.
Bagatelle
Fresh local seafood and creative cuisine are the stars at this elegant restaurant. Housed in a gorgeous and historic Duval St. location.
Bahama Village Shopping
Explore this diverse array of shops, boutiques, and galleries that showcase local art, crafts, and unique souvenirs in a charming and culturally rich neighborhood.
Better Than Sex
Stroll over to Better Than Sex, an intimate dessert restaurant offering a speakeasy-like atmosphere and tempting sweets and cocktails.
Blue Heaven
An eclectic menu, vibrant atmosphere and live music combine to create a unique and unforgettable dining experience at this restaurant nestled in a tropical garden.
Boat House Bar & Grill
Voted “Best Happy Hour in Key West,” this fun and friendly harborfront restaurant is the perfect place to eat and drink local favorites with an unbeatable view.
City of Key West Old Town Garage
Coffee Butler Amphitheater
Surrounded by tropical beauty, this amphitheater provides a vibrant setting to enjoy concerts, festivals and other entertainment experiences in the heart of Key West.
Danger Charters
Sail into the breathtaking beauty of the Florida Keys on unforgettable schooners designed to reveal both must-see landmarks and hidden gems.
Dante’s Pool Bar & Restaurant
Make a splash and enjoy the bustling atmosphere of Dante’s, an oasis of good times that combines sun, swimming, dancing, and all-day revelry. Perfect for bachelor, bachelorette and birthday parties.
Date & Thyme Organic Cafe & Market
Visit Key West’s best natural food market and the largest purveyor of organic and local produce. The cafe offers a menu of healthy smoothies and juices along with hearty breakfast and lunch favorites.
Ella’s Cottages
811 Simonton Street
Sit back and watch the world go by, just steps from some of the city’s best dining experiences. These charming bungalows exude the romance and carefree spirit of Key West.
Fitch Lodge
The ideal Key West basecamp for on-the-go explorers, island-hoppers and open-water adventurers. A neighborhood vibe welcomes you to go your own way in Key West.
Fury Water Adventures
For the ultimate water adventure, explore a wide range of watersports with Fury Water Adventures, your go-to source for sunset cruises, jet ski excursions, and more in Key West.
Green Parrot Bar
This legendary Key West watering hole is celebrated for its lively atmosphere and iconic live music. Residents and visitors are welcomed with vibrant energy and diverse entertainment offerings.
Greene Street Cigar Company
Immerse yourself in a world of premium cigars and a diverse menu of craft beer and wine, just a 2-minute walk from Ridley House. The walk-in humidor boasts Key West’s largest cigar selection.
Half Shell Raw Bar
Sample the freshest oysters, clams, shrimp and more at this scenic and friendly Key West institution that has been welcoming seafood lovers since 1972.
Kermit's Key West Lime Shoppe
Bright and colorful, with a diverse selection of treats that will keep you coming back again and again. Kermit has been serving sweets for over 30 years. Just four minutes from Ridley House.
Key West Cemetery
Established in 1847, this cemetery reflects Key West’s diverse cultural history. It’s a fascinating destination for visitors interested in exploring the eclectic charm of Key West.
Key West First Legal Rum Distillery
Discover the secrets behind Key West’s favorite spirit by embarking on a free distillery tour, a quick 4-minute walk from Ridley House. Savor free samples, relax at the bar, or purchase bottles to take home.
Key West Lighthouse
You can’t miss it! The Key West Lighthouse and Keeper’s Quarters are just 200 feet away from Lighthouse Hotel, offering an iconic backdrop for your Key West getaway.
Key West Pottery
Visit this unique studio known for its distinctive handcrafted ceramics that showcase a blend of artistic expression and functional design, all inspired by the vibrant spirit of Key West.
Key West Theater
Immerse yourself in Key West’s vibrant entertainment scene at the newly renovated Key West Theater, just a 3-minute stroll from Ridley House, offering the best in comedy, concerts, and live performances.
La Crêperie
This charming eatery specializes in French-style crepes served in a variety of sweet and savory options. It’s a favorite spot for anyone seeking a taste of authentic and delicious flavor.
Laid Back Key West
Welcome to Laid Back Key West! Looking for fun and adventure? Then it’s time to get out on the water. For over a decade, we have provided the best private charter boat tours in Key West. We want to take you, your family, and a few friends out on the spectacular warm turquoise waters of the Florida Keys.
Lighthouse Hotel
Colorful, energetic and welcoming, with the very best views of Key West’s famous lighthouse. Centrally located, a stone’s throw from Ernest Hemingway’s House. Afternoon daiquiris are calling.
Little Pearl
Taste the best of the local catch at Little Pearl Fish House & Wine Bar, a creative neighborhood dining destination on Olivia Street in the heart of Old Town.
Lola’s Bistro
Discover a charming eatery celebrated for its eclectic and inventive cuisine, offering a delightful fusion of global flavors and a welcoming ambiance.
Mangia Mangia Pasta Cafe
If you love homemade pasta and Italian specialties, you won’t want to miss this local favorite restaurant on Southard Street in the heart of Old Town Key West.
Moondog Café
If fresh baked goods, hearty meals and anytime beverages are your thing, grab a seat on the colorful patio of Moondog Cafe & Bakery. Just a 1-minute walk from Lighthouse Hotel.
Nine One Five Restaurant & Bar
Set in a beautifully restored 19th-century building on Duval Street, Nine One Five offers a sophisticated dining experience with a diverse menu featuring contemporary American cuisine, craft cocktails and an inviting atmosphere.
Old Town Bakery
Take a 2-minute stroll to Old Town Bakery to discover a diverse menu of pastries, sandwiches, and a key lime pie that was voted one of the best in the Florida Keys.
Onlywood Grill
Savor authentic Italian cuisine including homemade pastas, woodfire oven-baked pizzas, and tantalizing meats from an Argentinian grill.
OurKeyWest Galleria
From colorful Cuban art to the best of local makers, OurKeyWest Boutique offers a one-of-a-kind selection of gifts and handcrafts. A quick stroll up Simonton Street.
Papa’s Pilar Rum Distillery
For a refreshing taste of Key West’s rum culture, indulge in ice-cold cocktails at Papa’s Pilar Rum Distillery. A must see in Old Town, providing tours, tastings, and a journey into the art of rum-making.
Parking at Ella's Cottages
Limited on-site parking is available and can be inquired about at check in. $30 per night. Parking lot is located adjacent to Ella’s via Petronia St.
Parking at Fitch Lodge
No onsite parking available. Street and city lot parking available nearby.
Parking at Ridley House
No onsite parking available. Street and city lot parking available nearby.
Parking at Winslow's Bungalows
Limited on-site parking is available and can be inquired about at check in. $30 per night.
Pepe's Cafe & Steakhouse
A Key West classic, Pepe’s prides itself on being the “Oldest Eating House in the Keys”. Since 1909, it’s been serving up fresh local flavor and friendly vibes.
Ridley House
601 Caroline Street
Escape to the bohemian luxury of our elegant, adult-exclusive tropical mansion. Discover Old Town’s most romantic inn, around the corner from Key West Historic Seaport.
Santiago’s Bodega
Visit this tapas-style restaurant for an eclectic menu featuring a variety of shareable plates and sangria. Known for its lively atmosphere, extensive wine list, and diverse range of flavors.
Sarabeth's in Key West
Since 1981, Sarabeth’s has been serving up some of Key West’s favorite fare. Take a 4-minute stroll up Simonton Street and bring your appetite.
Seven Fish
Seafood lovers won’t want to miss a stop at Seven Fish, a casual bistro with dishes that feature the best of the local catch along with a menu of classic desserts and a deep wine list.
Sinz Burritos Key West
Savor the must-try street tacos, burritos, and quesadillas of Sinz Burritos on a short 5-minute stroll down Truman Street, where you can build your own or enjoy their unique takes on classics.
Splash Pad at Truman Waterfront Park
The perfect spot for kids to expend their energy and stay cool under the Key West sun, this lively splash pad offers refreshing and entertaining water experiences.
Sunset Sail Key West
Hit the water on a gorgeous fleet of schooners, including When and If—built in 1939 for General George S. Patton.
The Basilica of St. Mary Star of the Sea
Visit this historic Catholic church for its stunning architecture and rich history. Completed in 1905, the basilica is a popular site for visitors interested in Key West’s religious and architectural heritage.
The Green Pineapple
Shop this charming boutique for a curated selection of eco-friendly products and unique gifts. A cozy café, offers healthy bites, coffee, tea and organic wine.
The Hemingway Home and Museum
The spirit of one of Key West’s most iconic residents lives on. Tour the Hemingway Home & Museum, located right across the street from the Lighthouse Hotel.
The Key West Butterfly & Nature Conservatory
Step into a spectacular indoor environment featuring living butterflies and many colorful birds. This family-friendly sanctuary is a tropical paradise of waterfalls and plant life, with a gift shop offering unique souvenirs.
The Original Key West Ghost Hunt
Embark on a thrilling exploration of Key West’s ghostly past with The Original Key West Ghost Hunt.
The Waterfront Brewery
Combine scenic views with craft beer and island favorites at a picturesque local brewery, creating the perfect atmosphere for carefree Key West relaxation.
Vignette Key West
A boutique style destination in the heart of Key West for women who have their own story to tell. Take a 5-minute walk to Southard Street.
Vinos
Known for its extensive wine selection and Mediterranean-inspired menu, Vinos provides a delightful dining experience with a focus on pairing excellent wines with delicious dishes
ViV Wine Bistro
Authentic French fare combines with a sophisticated dining experience and an extensive selection of wines in a charming and cozy atmosphere. Bon appétit!
Winslow’s Bungalows
Play together among an eclectic collection of distinctly Key West structures. This lush green property invites every kind of carefree getaway, from family trips to wedding parties.
