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Poolside Dining & Drinks
Good food has a way of bringing people together. Across the Key West Historic Inns collection, every stay is just a short stroll from Isabel’s and The Bungalow Bar, where poolside lunches, tropical cocktails, and easy afternoons are always on the menu. Hotel guests can begin the day with complimentary breakfast before the doors open to locals and visitors, making both venues neighborhood favorites well into the evening.
eat + drink at winslow’s Bungalows
Bungalow Bar
Some places become part of your routine after just one visit. The Bungalow Bar at Winslow’s Bungalows is one of them. Poolside lunches turn into leisurely afternoons as fresh salads, burgers, tostadas, and island-inspired favorites arrive straight to your table.
Known for its signature Rum Punch, frozen cocktails, and tropical drinks, it’s the kind of place where one round naturally turns into another.
Surrounded by lush gardens and sparkling pools, The Bungalow Bar is just a short stroll from Lighthouse Hotel and the neighboring Key West Historic Inns, welcoming hotel guests, locals, and visitors to settle in and savor the easygoing pace of Old Town.
View A La Carte Breakfast Menu
open seven days a week
Bar: 8 AM – 8 PM
Happy Hour: 4 PM – 6 PM
Breakfast: 8 AM – 10 AM
Lunch: 11 AM – 2 PM
Located tucked inside Winslow’s Bungalows at 725 Truman Ave, Key West, FL 33040
Drink Specials at The Bungalow Bar
Rum, Lime & Sunshine Mondays
Buy One, Get One Margaritas & Mojitos
The best Mondays begin with sunshine, citrus, and a second round. Join us every Monday from 2–4 PM for buy one, get one margaritas and mojitos.
From Sunrise to Sunset Tuesdays
TITO’S DRINK SPECIALS ALL DAY
From your first cup to your last toast, enjoy Tito’s drink specials all day every Tuesday.
Wine Down Wednesdays
HALF OFF ALL WINES
Midweek calls for another pour. Join us from 6 PM until close for half off all wines.
Throwback Thursdays
$10 Classic Cocktails
Some classics never go out of style. Enjoy $10 classic cocktails all day every Thursday, featuring timeless favorites made just the way you remember.
Eat + drink at lighthouse hotel
Isabel’s
Steps from the legendary Hemingway Home & Museum, Isabel’s is Lighthouse Hotel’s inviting poolside bar and a favorite place to gather throughout the day. Start your morning with a specialty coffee and complimentary breakfast, then return for a relaxed lunch, handcrafted cocktails, and island-inspired favorites in a tropical setting.
No visit is complete without a classic mojito, famously one of Ernest Hemingway’s favorite cocktails during his years in Key West. Just moments from the home where he lived and wrote many of his most celebrated works, Isabel’s offers the perfect place to raise a glass and experience a piece of the island’s literary history while soaking up the laid-back atmosphere of Old Town.
View A La Carte Breakfast Menu
Open seven days a week
bar: 8AM – 6 PM
Happy Hour: 4 PM – 6 PM
Breakfast: 8 AM – 10 AM
Lunch: 11 AM – 2 PM
Located poolside at Lighthouse Hotel 902 Whitehead St, Key West, FL 33040
Drink Specials at Isabel's
Rum, Lime, and Sunshine Monday's
Buy One, Get One Margaritas & Mojitos
The best Mondays begin with sunshine, citrus, and a second round. Join us every Monday from 2–4 PM for buy one, get one margaritas and mojitos.
Flocktail Fridays
10% OFF your tab
Wear pink. Tag us. Raise a glass. Every Friday at Isabel’s, receive 10% off your tab when you wear pink and share your visit with us on social.
Live Music
LIVE MUSIC POOLSIDE
From laid-back mornings to lively afternoons, enjoy performances from talented local musicians at Winslow’s Bungalows and Lighthouse Hotel throughout the week. See what’s playing during your stay.