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Our top picks of the best holiday rentals in Old Town Key West
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Rose Lane Villas
Villa in Key West Historic District, Key West
Located in Key West, Florida, these villas feature a heated outdoor swimming pool. They are adjacent to dining and shopping on Duval Street. and 1.1 mi from the Southernmost Point.
A fully equipped kitchen is available in each villa at Rose Lane Villas. A flat-screen TV and DVD player are included. The private bathrooms offer a hairdryer and free toiletries. Select villas have a balcony or porch as well.
Free Wi-Fi is available, and the property offers parking
Key West Aquarium is 5 minutes’ walk from these villas. Guests will be 0.9 mi from the Ernest Hemingway Home and Museum.

Parrotville
Apartment in Old Town Key West, Key West
<h2>Spacious Accommodations</h2>
Parrotville in Key West offers a spacious apartment with two bedrooms and two bathrooms. The property features a balcony, air-conditioning, and a fully equipped kitchen.
<h2>Wellness and Parking</h2>
Guests can relax at the on-site spa and wellness center. Paid private parking is available on-site.
<h2>Local Attractions</h2>
South Beach is a 9-minute walk away, Ernest Hemingway Home and Museum 1969 feet nearby, and Duval Street an 8-minute walk. Key West International Airport is 2.5 mi from the property.
<h2>Nearby Activities</h2>
Water sports are available in the surrounding area.

Baya House
Holiday home in Old Town Key West, Key West
Baya House offers accommodations in Key West, a 18-minute walk from Key West Aquarium and one mile from Mallory Dock. This vacation home provides air-conditioned accommodations with a balcony. The property is 400 yards from the city center and a 7-minute walk from South Beach.
Providing a terrace and pool views, the spacious vacation home includes 2 bedrooms, a living room, satellite TV, an equipped kitchen, and 2 bathrooms with a walk-in shower and a bath. This vacation home also provides guests with a patio that doubles up as an outdoor dining area. For added privacy, the accommodation features a private entrance.
Guests can eat at the on-site restaurant.
Guests at the vacation home can enjoy cycling nearby, or make the most of the outdoor pool.
Popular points of interest near Baya House include Ernest Hemingway Home and Museum, Duval Street, and Southernmost Point. Key West International Airport is 2.5 miles away.

Breezy Retreat
Holiday home in Old Town Key West, Key West
<h2>Spacious Holiday Home in Key West</h2>
Breezy Retreat offers a spacious holiday home in Key West city center. The property features two bedrooms and two bathrooms, ensuring comfort for all guests.
<h2>Modern Amenities</h2>
Guests enjoy free WiFi in public areas, air-conditioning, a balcony, and a fully equipped kitchen with a washing machine. Additional amenities include a barbecue, tea and coffee maker, and a dishwasher.
<h2>Convenient Location</h2>
Located 2.5 mi from Key West International Airport, Breezy Retreat is a short walk from South Beach (2297 feet), Ernest Hemingway Home and Museum (1640 feet), and Duval Street (7-minute walk). Nearby attractions include Mallory Square and Key West Aquarium.
<h2>Local Activities</h2>
The surrounding area offers water sports, providing ample opportunities for outdoor enthusiasts.

Dancing Palms
Holiday home in Old Town Key West, Key West
Dancing Palms is located in Key West, just a 18-minute walk from Key West Aquarium and one mile from Mallory Dock. Featuring a restaurant, the property also has pool with a view. The property is 400 yards from the city center and a 6-minute walk from South Beach.
The vacation home consists of 2 separate bedrooms, 2 bathrooms, and a living room. The accommodation is non-smoking.
Guests at the vacation home will be able to enjoy activities in and around Key West, like cycling. A children's playground is also available for guests at Dancing Palms.
Popular points of interest near the accommodation include Ernest Hemingway Home and Museum, Duval Street, and Southernmost Point. Key West International Airport is 2.5 miles from the property.

Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool
Cottage in Old Town Key West, Key West
With a stay at this cottage in Key West (Old Town Key West), you'll be a 4-minute walk from Duval Street and 11 minutes by foot from Florida Keys Beaches. This cottage is 0.3 mi (0.5 km) from Ernest Hemingway Home and Museum and 0.6 mi (1 km) from South Beach.

KW37 Oceana Suite
Apartment in Old Town Key West, Key West
<h2>Comfortable Living</h2>
KW37 Oceana Suite in Key West offers a one-bedroom apartment with a living room. The property includes air-conditioning, a washing machine, and a fully equipped kitchen with a refrigerator, microwave, dishwasher, oven, stovetop, toaster, and tea and coffee maker.
<h2>Outdoor Leisure</h2>
Guests can relax by the outdoor swimming pool and enjoy the sun. The apartment features a shower, hairdryer, and TV for added comfort.
<h2>Prime Location</h2>
Located in the city center, the apartment is less than 0.6 mi from South Beach and Ernest Hemingway Home and Museum. Duval Street is 1969 feet away, while Key West Aquarium is 0.9 mi from the property. Key West International Airport is 1.9 mi distant.
<h2>Nearby Attractions</h2>
Southernmost Point is a 13-minute walk, Mallory Square is 1 mi, and Jackson Square is 12 minutes on foot. Water sports are available in the surrounding area. Highly rated by guests.

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!
Cottage in Old Town Key West, Key West
With a stay at this cottage in Key West (Old Town Key West), you'll be a 3-minute walk from Duval Street and 6 minutes by foot from Florida Keys Beaches. This cottage is 0.4 mi (0.6 km) from South Beach and 0.4 mi (0.6 km) from Ernest Hemingway Home and Museum.

Amelia Home by AvantStay
Holiday home in Old Town Key West, Key West
<h2>Spacious Holiday Home in Key West</h2>
Amelia Home by AvantStay offers a spacious holiday home in Key West city center. Guests enjoy a private entrance and a fully equipped kitchen with modern appliances.
<h2>Outdoor Pool and Free WiFi</h2>
The property features an outdoor swimming pool and free WiFi, providing relaxation and connectivity. Additional amenities include air-conditioning, a washing machine, and a patio with pool views.
<h2>Convenient Location</h2>
South Beach is a 5-minute walk away, while the Southernmost Point lies 2297 feet nearby. Ernest Hemingway Home and Museum is a 7-minute walk, and Duval Street is 2625 feet from the property. Key West International Airport is 2.5 mi distant.
<h2>Nearby Attractions</h2>
Guests can explore Southernmost Point, Ernest Hemingway Home, and Duval Street. Key West Aquarium and Mallory Square are 1.1 mi away, while Mallory Dock and Mallory Square are 1.2 mi from the property. Water sports are available in the surroundings.

Amelia Home by Avantstay In Historic Old Town w/ Pool
Cottage in Old Town Key West, Key West
With a stay at this cottage in Key West (Old Town Key West), you'll be a 3-minute walk from Duval Street and 6 minutes by foot from Florida Keys Beaches. This cottage is 0.4 mi (0.6 km) from South Beach and 0.4 mi (0.6 km) from Ernest Hemingway Home and Museum.

Sailors Cabin - Prime Downtown Key West Spot - Walk to Duval
Apartment in Old Town Key West, Key West
<h2>Prime Downtown Location</h2>
Sailors Cabin in Key West offers a central position with Duval Street 1969 feet away and South Beach an 8-minute walk. Nearby attractions include Ernest Hemingway Home and Museum, Southernmost Point, and Key West Aquarium. Key West International Airport is 2.5 mi from the property.
<h2>Comfortable Living</h2>
The apartment features one bedroom, one bathroom, and a living room. Guests enjoy air-conditioning, a fully equipped kitchen, and a TV. Private check-in and check-out services ensure a smooth arrival and departure.
<h2>Outdoor Spaces</h2>
A terrace provides a relaxing outdoor area, while free WiFi is available throughout the property. Additional amenities include an outdoor seating area, picnic area, and bike hire.
<h2>Guest Satisfaction</h2>
Highly rated for its convenient location, room cleanliness, and comfort, Sailors Cabin offers a pleasant stay in Key West.

Old Town Garden Villas - Abaco Suite
Apartment in Old Town Key West, Key West
Old Town Garden Villas - Abaco Suite is located in Key West, just a 17-minute walk from Key West Aquarium and 0.9 miles from Mallory Dock. The apartment has access to a restaurant. The property is 300 yards from the city center and a 8-minute walk from South Beach.
The air-conditioned apartment consists of 1 bedroom, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with a walk-in shower and a hair dryer. Towels and bed linen are provided in the apartment. The property has an outdoor dining area.
Guests at the apartment can enjoy cycling nearby, or make the most of the outdoor pool.
Popular points of interest near Old Town Garden Villas - Abaco Suite include Duval Street, Ernest Hemingway Home and Museum, and Southernmost Point. Key West International Airport is 2.5 miles away.

Duval Breeze by AvantStay
Holiday home in Old Town Key West, Key West
<h2>Spacious Holiday Home</h2>
Duval Breeze by AvantStay in Key West offers a spacious setting with two bedrooms and a comfortable living room. The property includes a fully equipped kitchen, balcony, and patio, ensuring a pleasant stay.
<h2>Outdoor Amenities</h2>
Guests can enjoy an outdoor swimming pool and free WiFi, perfect for relaxation and connectivity. The holiday home features air-conditioning, a washing machine, and free toiletries, catering to all comfort needs.
<h2>Prime Location</h2>
Located in the city center, Duval Breeze is a short walk from South Beach (1969 feet), Ernest Hemingway Home and Museum (1640 feet), and Duval Street (2297 feet). Key West International Airport is 2.5 mi away, providing convenient travel options.
<h2>Nearby Attractions</h2>
Explore Southernmost Point (1969 feet), Key West Aquarium (18-minute walk), Mallory Square (1.1 mi), and other attractions within walking distance. Water sports are available in the surrounding area, enhancing the holiday experience.

New Casa Caribe by Brightwild- Two-Story Condo Rooftop Pool
Holiday home in Old Town Key West, Key West
<h2>Spacious Accommodations</h2>
New Casa Caribe by Brightwild offers a spacious holiday home in Key West. The property features two bedrooms, three bathrooms, and a comfortable living room.
<h2>Outdoor Amenities</h2>
Guests can enjoy an outdoor swimming pool and an outdoor seating area. Free on-site private parking is available, ensuring convenience.
<h2>Modern Facilities</h2>
The home includes air-conditioning, a washing machine, and a fully equipped kitchen with a refrigerator, microwave, dishwasher, and oven. Additional amenities include a dining table, TV, and free toiletries.
<h2>Prime Location</h2>
Located in the city center, the property is a short walk from South Beach (1969 feet), Ernest Hemingway Home and Museum (1640 feet), and Duval Street (7-minute walk). Key West International Airport is 2.5 mi away. Water sports are available in the surroundings. Highly rated for its convenient location.

Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
Cottage in Old Town Key West, Key West
With a stay at this cottage in Key West (Old Town Key West), you'll be steps from Duval Street and 7 minutes by foot from Florida Keys Beaches. This cottage is 0.3 mi (0.5 km) from Ernest Hemingway Home and Museum and 0.3 mi (0.5 km) from South Beach.

Duval Sea Turtle by AvantStay
Holiday home in Old Town Key West, Key West
<h2>Spacious Holiday Home in Key West</h2>
Duval Sea Turtle by AvantStay offers a spacious holiday home in Key West city center. Guests enjoy a private entrance and pool views.
<h2>Outdoor Pool and Free WiFi</h2>
The property features an outdoor swimming pool and free WiFi. Additional amenities include a hot tub and air-conditioning.
<h2>Comfortable Living Spaces</h2>
The home consists of two bedrooms, two bathrooms, and a living room. A fully equipped kitchen includes a coffee machine, dishwasher, and oven.
<h2>Nearby Attractions</h2>
South Beach is a 6-minute walk away, Ernest Hemingway Home and Museum 1640 feet, and Duval Street 7-minute walk. Key West International Airport is 2.5 mi distant. Water sports are available in the surroundings.
<h2>Highly Rated by Guests</h2>
Guests appreciate the spaciousness and excellent facilities.

Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays
Cottage in Old Town Key West, Key West
With a stay at this cottage in Key West (Old Town Key West), you'll be steps from Duval Street and 7 minutes by foot from Florida Keys Beaches. This cottage is 0.3 mi (0.5 km) from Ernest Hemingway Home and Museum and 0.3 mi (0.5 km) from South Beach.

Casabella Duval Square
Apartment in Old Town Key West, Key West
Just a 5-minute walk from Ernest Hemingway Home and Museum and 700 yards from Duval Street, Casabella Duval Square features accommodations in Key West with a spa and wellness center. Private parking is available on site. The property is a 6-minute walk from South Beach and within 400 yards of the city center.
The air-conditioned apartment consists of 2 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 1 bathroom with a bath and a hair dryer. Towels and bed linen are provided in the apartment. The property has an outdoor dining area.
Popular points of interest near the apartment include Southernmost Point, Key West Aquarium, and Mallory Dock. Key West International Airport is 2.5 miles away.

Road s End by Brightwild Steps to Duval St
Apartment in Old Town Key West, Key West
With a stay at this apartment in Key West (Old Town Key West), you'll be steps from Duval Street and 8 minutes by foot from Florida Keys Beaches. This apartment is 0.2 mi (0.3 km) from Ernest Hemingway Home and Museum and 0.5 mi (0.8 km) from Southernmost Point.

Road's End
Apartment in Old Town Key West, Key West
Road's End offers accommodations in Key West, a 16-minute walk from Key West Aquarium and 0.9 miles from Mallory Dock. This apartment features air-conditioned accommodations with a patio. The property is 200 yards from the city center and a 8-minute walk from South Beach.
With free Wifi, this 1-bedroom apartment provides a cable TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are provided in the apartment. The accommodation is non-smoking.
Guests can enjoy the outdoor swimming pool and garden at the apartment.
Popular points of interest near Road's End include Duval Street, Ernest Hemingway Home and Museum, and Southernmost Point. Key West International Airport is 2.5 miles away.
