Old Town Key West vacation rentals

We found 1,611 vacation rentals — enter your dates for availability

Select from 573 houses, 258 condos, and other vacation rentals to find the perfect place for your stay in Old Town Key West. Whether you’re staying in a vacation home with a group or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include a hot tub and a washer and dryer. Whatever you're looking for, you'll find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

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Find out more about Old Town Key West

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.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January71.1°F (21.7°C)No Rain (Dry)Mostly SunnySlightly HighAverage
February72.1°F (22.3°C)No Rain (Dry)Mostly SunnySlightly HighAverage
March73.4°F (23.0°C)No Rain (Dry)Mostly SunnySlightly HighSlightly High
April76.8°F (24.9°C)No Rain (Dry)Mostly SunnyAverageSlightly High
May79.3°F (26.3°C)Light RainMostly SunnyAverageAverage
June82.6°F (28.1°C)Light RainMostly SunnyAverageSlightly Low
July84.0°F (28.9°C)Light RainMostly SunnyAverageAverage
August84.4°F (29.1°C)Light RainMostly SunnySlightly LowSlightly Low
September83.7°F (28.7°C)Light RainMostly SunnySlightly LowSlightly Low
October80.8°F (27.1°C)Light RainMostly SunnySlightly LowAverage
November76.6°F (24.8°C)Light RainMostly SunnyAverageAverage
December73.9°F (23.3°C)No Rain (Dry)Mostly SunnyAverageSlightly 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.

Unlock savings with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll earn OneKeyCash on the full booking amount. Being the organizer certainly has its perks. Become a member of our One Key rewards program to unlock exclusive savings and earn OneKeyCash on eligible stays. Sign up today and begin reaping the benefits.

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.

Frequently asked questions

What is the most popular type of vacation rental in Old Town Key West?
In Old Town Key West, vacation houses are the most popular type of rental accommodation, with around 549 available throughout the area. These properties are often situated in charming neighborhoods, providing a quintessential Key West experience close to attractions like the Ernest Hemingway Home and Museum and the vibrant nightlife on Duval Street. Most vacation houses feature spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor spaces such as patios or gardens, superb for enjoying the warm Florida weather.

Additionally, there are about 246 condos available, which typically offer amenities like pools, fitness centers, and easy access to nearby beaches. Apartments, numbering around 139, provide a more compact and affordable option, often including full kitchens and cozy living areas. For those seeking a quaint retreat, there are roughly 79 cottages, which usually have charming decor and outdoor seating areas. Lastly, a few villas, totaling around 15, offer luxury hotels with private pools and upscale amenities.
Are there any beach house rentals in Old Town Key West?
In Old Town Key West, beach house rentals are abundant, with approximately 1,442 properties available. These rentals are primarily located in the vibrant heart of the area, close to iconic landmarks such as Duval Street, the Ernest Hemingway Home and Museum, and the picturesque waterfront. Travelers can expect a variety of amenities, including spacious living areas, fully equipped kitchens, private pools, and outdoor patios ideal for enjoying the warm Florida weather. Many beach houses also feature unique architectural styles that reflect the charm of Key West, providing a cozy and inviting atmosphere for guests.
How much does it cost to rent a vacation home in Old Town Key West?
Prices for vacation rentals in Old Town Key West vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Old Town Key West to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Old Town Key West vacation house rentals?
You can find great discounts on house rentals in Old Town Key West on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Old Town Key West?
In Old Town Key West, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals and enjoy a home-like experience. Travelers can also expect coffee and tea makers for their morning brews, along with outdoor spaces such as decks or patios for relaxing in the warm Florida weather. Onsite parking is another convenient amenity, suiting those who may bring their vehicles to explore the vibrant local area, which is near popular attractions like the Ernest Hemingway Home and Museum and the lively Duval Street.
Can I find family house rentals in Old Town Key West?
In Old Town Key West, there are around 624 family-friendly vacation rentals available, making it a fantastic destination for families. Many of these homes offer spacious living areas, full kitchens for preparing family meals, and outdoor spaces where children can play and adults can relax. Visitors can expect amenities like private pools, outdoor dining areas, and convenient access to local attractions.

This vibrant neighborhood is just a short stroll from iconic spots such as the Ernest Hemingway Home and Museum and the lively Duval Street, where families can explore local shops and restaurants. The close proximity to beaches and parks also ensures that outdoor activities are never far away.
Can I rent a vacation home with a pool or hot tub in Old Town Key West?
In Old Town Key West, there are plenty of vacation homes available for rent that feature both pools and hot tubs, with around 808 options offering pools and 114 options with hot tubs. This vibrant neighborhood is known for its historic charm, colorful architecture, and proximity to the lively Duval Street, making it a sought-after destination for travelers.

Visitors can expect various amenities in these rentals, including private pools superb for cooling off after a day of exploring, as well as hot tubs for relaxing under the stars. Many properties come with outdoor patios or decks, fully equipped kitchens, and spacious living areas, ideal for family gatherings or group vacations.
Are there any Old Town Key West vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Old Town Key West with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I book pet-friendly vacation rentals in Old Town Key West?
Yes, you can book pet-friendly vacation rentals in Old Town Key West, with a top availability of 357 options. This vibrant area is known for its lively option, historic architecture, and proximity to the stunning beaches and attractions of Key West. Many of the vacation rentals in Old Town come equipped with modern amenities such as private pools, outdoor patios, and fully equipped kitchens, making them superb for families or groups traveling with pets.

In terms of pet-friendly points of interest, the nearby Dog Beach offers a welcoming space for pets to play and enjoy the ocean, while local parks provide additional opportunities for walks and outdoor activities. Old Town's close-knit community also features pet-friendly restaurants and cafes, allowing travelers to enjoy the local cuisine while accompanied by their furry friends.
Can I find long-stay vacation rentals in Old Town Key West?
A long-stay vacation rental in Old Town Key West is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Old Town Key West for a vacation rental?
The best time to visit Old Town Key West for a vacation rental is during the peak season from January to March, with March being particularly popular. This vibrant time attracts travelers seeking to enjoy the area's lively option, beautiful beaches, and rich cultural experiences. With average temperatures ranging from the mid-60s to mid-80s Fahrenheit, the weather is superb for outdoor activities like strolling along the historic streets, visiting local art galleries, or relaxing at the beach.

During these months, you can immerse yourself in the bustling energy of the island, as visitors flock to enjoy events like the famous Fantasy Fest and various live music performances. The warm, sunny climate sets the stage for both relaxation and adventure, whether you're snorkeling in the crystal-clear waters or savoring fresh seafood at local restaurants.

If you're looking for a more budget-friendly option, consider visiting in October. This month offers a quieter experience, superb for those who prefer a more laid-back atmosphere. You can still enjoy the beauty of the island and explore its attractions without the crowds, making it a delightful time for leisurely walks and discovering hidden gems.

Ultimately, whether you choose the lively peak season or the serene fall months, Old Town Key West offers a variety of experiences that cater to diverse travel preferences.
Are there any remote work vacation rentals in Old Town Key West?
In Old Town Key West, there are numerous remote work vacation rentals available, with around 1,009 options to choose from. This vibrant area, known for its historic charm and lively option, offers a variety of accommodations that cater to remote workers. Many of these rentals feature essential amenities such as high-speed internet, free Wi-Fi, and dedicated workspaces, ensuring a productive environment for those working remotely.

Travelers can expect to find properties equipped with comfortable desks and cozy living areas, making it easy to balance work and leisure. Additionally, the proximity to attractions like the Ernest Hemingway Home and Museum, local shops, and the famous Duval Street adds to the appeal, allowing for enjoyable breaks after work hours. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Old Town Key West vacation rental?
Book your Old Town Key West vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Old Town Key West, Florida, United States of America?
In Old Town Key West, visitors can engage in the island's rich history and vibrant culture. One of the top attractions is the Ernest Hemingway Home and Museum, where travelers can explore the author's former residence and see the famous six-toed cats. Nearby, the Key West Lighthouse offers stunning views of the island after a climb up its historic steps.

Duval Street is the bustling heart of Old Town, lined with bars, restaurants, and shops, making it a great spot for nightlife and dining. The southernmost point buoy is also nearby, marking the southernmost point in the continental United States and providing a popular photo opportunity.

For those interested in nature, the beautiful beaches such as Fort Zachary Taylor Historic State Park offer opportunities for swimming, sunbathing, and picnicking.
Can I change or cancel my Old Town Key West home rental booking on Vrbo?
To find Old Town Key West vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Old Town Key West vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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