Bootlegger Bay @ Speakeasy Inn Key West! Exterior photoBootlegger Bay @ Speakeasy Inn Key West! Exterior photoBootlegger Bay @ Speakeasy Inn Key West! Exterior photo
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From409US$ /night
Check-in
02May2026Select date
Check-out
03May2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

Hotel Overview

1117 Duval St., Key West, Florida, United States
-
Close to Duval Street

Location

Bootlegger Bay @ Speakeasy Inn is situated in the heart of Key West, allowing easy access to local attractions such as Mallory Square and Duval Street. The nearby beaches provide guests with a variety of water activities. This hotel is conveniently located within walking distance of historical sites and vibrant nightlife.

Dining

The hotel offers a full-service restaurant that specializes in Southern-inspired dishes, catering to diverse culinary tastes. Guests can enjoy a casual atmosphere while savoring hearty breakfasts and delightful dinners. The bar provides a selection of local beers and signature cocktails, perfect for unwinding after a day of exploration.

Rooms

Bootlegger Bay has 16 uniquely designed rooms, each equipped with a refrigerator and microwave for added convenience. Some rooms feature private patios, offering an outdoor space to relax and unwind. The variety of layouts accommodates couples and small groups effectively.

Amenities

The hotel boasts a beautiful outdoor pool, ideal for cooling off on warm Key West days. Guests can take advantage of the lush garden area for sunbathing or relaxing with a book. On-site parking and bike rentals add to the convenience of staying at Bootlegger Bay.

Entertainment

Guests at Bootlegger Bay can enjoy a lively entertainment schedule that includes live music and themed events hosted by the hotel. Local activities, including sunset sails and fishing charters, can be arranged at the front desk. The vibrant atmosphere of the surrounding area offers endless options for nightlife and cultural experiences.

Highlights

Location: Close to Mallory Square and beaches

Dining: Southern-inspired dishes at on-site restaurant

Rooms: 16 uniquely designed rooms with private patios

Amenities: Beautiful outdoor pool and lush garden area

Must-do experiences

  • Visit the Ernest Hemingway Home for a glimpse into his life.
  • Try the Key Lime Pie at Kermit's for an authentic taste.
  • Explore the vibrant local art scene at the Galleries of Key West.
  • Catch the sunset celebration at Mallory Square for street performers.
  • Stroll through the historic Fort Zachary Taylor for stunning views.
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Choose Your Room

Our listed hotels offer a variety of room types—double rooms, family suites, or deluxe options—all with features like breakfast, flexible cancellation policies, and exclusive deals.
One-Bedroom Apartment
2 persons
Shower
Jacuzzi

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Amenities

Thoughtful hotel amenities for a comfortable stay

General

  • No smoking on site
  • Parking
  • No pets allowed

Sports & Fitness

  • Snorkelling
  • Tennis court
  • Golf course
  • Fishing

Spa & Leisure

  • Beach access
  • Jacuzzi

Room features

  • Free Wi-Fi in rooms
  • Tea and coffee facilities
  • Ironing facilities

Media

  • Flat-screen TV
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Hotel Location

1117 Duval St., Key West, Florida, United States
Map view
1117 Duval St., Key West, Florida, United States
Nearby
Museum
The Ernest Hemingway Home and Museum
1500 ft
Duval Street
Duval Street
1900 ft
cnr South & Whitehead Sts
Southernmost Point
1600 ft
Nature reserve
Key West Butterfly and Nature Conservatory
900 ft
Monument
Southernmost Point of the Continental US
1600 ft
938 Whitehead St
Key West Lighthouse and Keeper's Quarters Museum
1000 ft
Church
Saint Mary Star of the Sea
1500 ft
Gallery
Island Arts Co-op
200 ft
Gallery
Alan S Maltz Gallery
400 ft
Gallery
Frangipani Gallery
200 ft
Gallery
Key West Pottery
300 ft
South Street Corner of South and Whithead Streets
Statue Of Bishop Albert Kee
1800 ft
Gallery
Wild Side Gallery
700 ft
1100 Simonton St
Historic E. H. Gato Building
600 ft
Museum
Tennessee Williams Key West Exhibit
800 ft
Gallery
Art On Duval Key West
1700 ft
Restaurants
Flamingo Crossing
300 ft
1105 Duval Street
Sinz Burritos
800 ft
500 Truman Ave Unit 1
Key West Cuban Coffee
900 ft
517 Truman Ave Key West
Tropical Juices & Drinks
800 ft
925 Duval St
Ana's Cuban Cafe
2400 ft
1330 Simonton St
Bobby's Monkey Bar
1500 ft
900 Simonton St
La Bodeguita del Medio Key West
1300 ft
722 Duval St Duval / Petronia next to Bourbon Street Pub
Explore Key West
Explore Key West
Top Attractions
Activities
Dining
Entertainment
Key West Butterfly and Nature Conservatory
4 minutes walking
A stunning habitat with hundreds of butterflies and exotic birds, offering guided tours and a serene atmosphere.
Southernmost Point of the Continental US
6 minutes walking
An iconic landmark featuring a buoy that marks the southernmost point in the continental U.S., perfect for photos.
Ernest Hemingway Home and Museum
6 minutes walking
The former residence of the author, showcasing his life and works, with guided tours available daily.
Key West Aquarium
19 minutes walking
A family-friendly aquarium featuring local marine life and interactive exhibits, offering tours and feedings.
Snorkeling Tours
5 minutes drive
Adventurous snorkeling tours available nearby, with rental services and guided options to explore vibrant reefs.
Yoga Classes
5 minutes drive
Relaxing beach yoga classes offered a short drive away, perfect for stress relief and enjoying the ocean breeze.
Biking Around Key West
5 minutes walking
Bike rentals available within walking distance, an ideal way to explore the streets and scenic views of Key West.
Sunset Cruises
5 minutes drive
Romantic sunset cruise experiences available, featuring breathtaking views and refreshments on board.
The Restaurant at La Te Da
1 minute walking
An elegant dining experience with local seafood and craft cocktails, known for its vibrant atmosphere.
Grand Vin
1 minute walking
A cozy wine bar offering a selection of fine wines and gourmet small plates in a relaxed ambiance.
Ocean Grill & Bar
2 minutes walking
Casual beachfront dining with fresh seafood and stunning ocean views, ideal for families and groups.
La Grignote
2 minutes walking
Charming eatery serving breakfast and French-inspired brunch, famous for its crepes and pastries.
Sloppy Joe's
10 minutes walking
A lively bar known for live music and a vibrant atmosphere, hosting events throughout the week.
The Studios of Key West
15 minutes walking
An arts hub offering exhibitions, performances, and classes, fostering cultural engagement for all ages.
Red Barn Theatre
15 minutes walking
A popular venue for local theater productions, known for its eclectic programming and engaging performances.
Rick's Bar
8 minutes walking
A bustling nightlife spot featuring DJs and dance floors, perfect for an energetic evening out.
Transportation Tips
City Centre
Key West21 min  ·  1.1 mi
Airports
Key West International (EYW)9 min  ·  3.7 mi
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Property information and rules
Check-in
from 15:00-23:59
Check-out
until 11 am
Internet
Wireless internet is available in the hotel rooms for free.
Pets
Pets are not allowed.

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Check-in
02May2026Select date
Check-out
03May2026Select date
Rooms and Guests2 Guests, 1 Room