Old Town Key West vacation rentals

Why visit Old Town Key West

• Historic Landmarks: Discover iconic sites like the Ernest Hemingway Home and Museum and the Southernmost Point Buoy.
• Picturesque Streets: Stroll through charming neighborhoods filled with vibrant architecture and colorful houses.
• Beautiful Beaches: Relax on stunning beaches, perfect for swimming, sunbathing, and enjoying water activities.
• Cultural Experiences: Immerse yourself in the rich local culture with galleries, live music, and unique events.
• Diverse Accommodations: Choose from cozy cottages, inviting condos, and historic vacation homes to suit any budget.

Popular types of accommodation around Old Town Key West

If you're planning a trip to Old Town Key West, you're in for a treat. Our most popular vacation rental options include charming Houses, inviting Condos, and cozy Cottages. Whether you're looking for historic Key West vacation rentals or modern comforts, we have a variety of Old Town rentals that cater to every taste and budget. Experience the vibrant culture and stunning scenery of Key West with the perfect place to stay.

• Houses: The top choice for visitors to Old Town Key West, offering spacious and comfortable accommodations perfect for families and groups.
• Condos: A popular option for travelers seeking modern amenities and convenient locations, ideal for couples or small families.
• Cottages: These charming and quaint retreats provide a cozy atmosphere, perfect for a romantic getaway or solo escape.
• Apartments: A practical choice for travelers looking for affordability and easy access to local attractions.
• Villas: Luxurious and spacious, villas are perfect for those seeking an upscale experience in a tropical setting.**

Top attractions in and around Old Town Key West

Old Town Key West offers a vibrant blend of culture, beaches, and city experiences, making it perfect for family and business-themed vacations. Explore iconic landmarks, stroll along picturesque streets, and relax on beautiful beaches. Whether you're interested in the historic district or seeking vacation ideas, Old Town Key West has something for everyone to enjoy during their stay.

• Duval Street: A vibrant thoroughfare in Key West, Duval Street is known for its lively atmosphere, featuring an array of shops, bars, and restaurants. It's a perfect spot for people-watching and soaking in the local culture.
• Southernmost Point: This iconic landmark marks the southernmost point in the continental United States. It’s a popular photo opportunity, reflecting the unique culture and laid-back vibe of Key West.
• Ernest Hemingway Home and Museum: Step into literary history at this preserved home of the famous author. The museum showcases Hemingway’s life and work, surrounded by lush gardens and intriguing architecture.

Things to do recommended for couples

Ready for a romantic getaway in Old Town Key West? Enjoy a sunset sail on a classic schooner, explore the charming streets hand-in-hand, and indulge in a candlelit dinner at a waterfront restaurant. Don’t miss the vibrant sunset celebration at Mallory Square.

Things to do recommended for families

Your family will love splashing around at the MLK Community Pool & Community Center, where you can enjoy a vibrant atmosphere filled with sports and outdoor activities. This local gem in Old Town Key West is perfect for a day of fun and relaxation together.

Things to do recommended for groups

Enjoy a round of golf with friends at the Key West Golf Club, just 4 miles away, or catch a captivating show at the Waterfront Playhouse, only 0.8 miles from Old Town. Don’t forget to stop by The Kite House for unique local souvenirs.

What do I need to keep in mind when booking a vacation around Old Town Key West

When traveling with a group, family, or pets, or if you're considering longer stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

• Traveling to Old Town Key West with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for all these options and more on Vrbo.
• Traveling to Old Town Key West with young kids: Traveling with little ones can be quite an adventure. It's important to prioritize their comfort and safety, along with amenities that cater to their age, like a private swimming pool. Additionally, keeping in mind how close you are to family-friendly attractions can enhance your experience.
• Taking your pets with you to Old Town Key West: For many families, a vacation isn't truly fulfilled without their furry companion. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
• Planning for a long term stay visiting Old Town Key West: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Old Town Key West

Old Town Key West offers a vibrant mix of history, adventure, and tropical charm. Visitors can explore historic homes, stroll through picturesque neighborhoods, and immerse themselves in the unique atmosphere of this iconic destination. From family-friendly excursions to business-themed retreats, there’s something for everyone in and around Old Town. Don't miss the chance to experience the rich culture and stunning scenery that make Key West an unforgettable vacation spot.

• Key West: Key West is a vibrant island city known for its tropical charm and relaxed atmosphere. Located at the southernmost point of the continental United States, it offers visitors a unique blend of cultural experiences and activities. Travelers can enjoy a variety of attractions such as beautiful beaches, lively shopping centers, and family-friendly resorts. The city is also famous for its stunning sunsets and bustling nightlife, making it an ideal destination for families, business travelers, and those seeking a city-themed experience. Explore the local landmarks, relax on the sandy shores, and immerse yourself in the lively streets filled with shops and eateries.
• Key West Historic District: Situated just 0.3 miles from Old Town Key West, the Key West Historic District is a captivating neighborhood that showcases the island's rich history and unique architecture. Visitors are drawn to its quaint streets lined with beautifully preserved homes and historical landmarks. The area is perfect for families and history buffs alike, offering access to shopping areas and local resorts. Here, you can stroll along the picturesque streets, relax at family-friendly beaches, and indulge in the local culture. The Historic District serves as a delightful backdrop for those seeking a city-themed vacation experience.
• Downtown Key West: Located only 0.2 miles from Old Town Key West, Downtown Key West is the heart of the island's vibrant culture. This lively neighborhood is bustling with shops, restaurants, and entertainment venues, making it an ideal spot for families and business travelers. Visitors can enjoy a plethora of activities, from exploring local boutiques to unwinding at nearby beaches. The atmosphere is infused with a blend of history and modernity, offering a city-themed experience that captures the essence of Key West. Whether you're looking to shop, dine, or explore, Downtown Key West has something for everyone.

Best time to go to Old Town Key West

If you're planning a trip to Old Town Key West, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from January to March, while off-peak times, like August to October tend to have fewer bookings and better deals.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	71.1°F (21.7°C)	No Rain (Dry)	Mostly Sunny	Slightly High	Average
February	72.1°F (22.3°C)	No Rain (Dry)	Mostly Sunny	Slightly High	Average
March	73.4°F (23.0°C)	No Rain (Dry)	Mostly Sunny	Slightly High	Slightly High
April	76.8°F (24.9°C)	No Rain (Dry)	Mostly Sunny	Average	Slightly High
May	79.3°F (26.3°C)	Light Rain	Mostly Sunny	Average	Average
June	82.6°F (28.1°C)	Light Rain	Mostly Sunny	Average	Slightly Low
July	84.0°F (28.9°C)	Light Rain	Mostly Sunny	Average	Average
August	84.4°F (29.1°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
September	83.7°F (28.7°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
October	80.8°F (27.1°C)	Light Rain	Mostly Sunny	Slightly Low	Average
November	76.6°F (24.8°C)	Light Rain	Mostly Sunny	Average	Average
December	73.9°F (23.3°C)	No Rain (Dry)	Mostly Sunny	Average	Slightly High

Booking with Vrbo is a breeze

Are you hoping to cut costs on your upcoming trip? Being open to adjusting your travel dates can help, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to narrow down options by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board feature offers a convenient way to plan your travels. You can start new trips, pick up where you left off, or manage your existing plans all in one place. Any properties you’ve saved or booked are easily accessible in the Potential, Upcoming, or Current Trips sections. To explore Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.