Old Town Key West vacation rentals

We found 1,625 vacation rentals — enter your dates for availability

Select from 632 houses, 257 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 approximately 638 available throughout the area. These houses often feature charming architecture and provide ample space for families or groups, including multiple bedrooms, fully equipped kitchens, and outdoor patios or decks ideal for enjoying the tropical climate. Condos are also a significant option, with around 271 rooms available, typically offering modern amenities like pools, fitness centers, and proximity to the vibrant nightlife and dining options of Duval Street. Additionally, there are 127 apartments and 91 cottages, providing travelers with various choices that emphasize comfort and convenience.
Are there any beach house rentals in Old Town Key West?
In Old Town Key West, there are approximately 1,833 beach house rentals available, making it a popular destination for vacationers. These rentals are typically situated in vibrant neighborhoods close to attractions like the Ernest Hemingway Home and Museum, Duval Street's lively nightlife, and the picturesque waterfront. Travelers can expect a variety of amenities in these beach house rentals, including spacious living areas, fully equipped kitchens, private pools, and outdoor patios for enjoying the tropical climate. Many properties also feature unique decor that reflects the island's charm, making for a memorable stay. Find your rental near the beach in Old Town Key West.
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 vacation rental amenities include fully equipped kitchens, allowing guests to prepare their own meals, as well as patios for enjoying the warm Florida weather. Many rentals also feature heated pools, which provide a comfortable swimming experience year-round, with some properties offering shared pool access for a social atmosphere.
Are there any family house rentals in Old Town Key West?
In Old Town Key West, travelers will find a wealth of family-friendly house rentals, with around 630 available options. This vibrant neighborhood is known for its charming streets and proximity to iconic attractions like the Ernest Hemingway Home and Museum and the lively atmosphere of Duval Street. Many of these homes come with spacious living areas, full kitchens for family meals, and outdoor spaces superb for relaxation or play.

Additionally, these properties often include amenities such as private pools, outdoor grilling stations, and beach gear for a fun-filled day by the ocean. Families can easily access nearby parks and beaches, ensuring that there are plenty of activities to keep everyone entertained. See all family-friendly rentals in Old Town Key West.
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 come with pools and hot tubs, with around 870 options featuring pools and 133 with hot tubs. This vibrant area is known for its historic charm and close proximity to beautiful beaches, making it an ideal choice for travelers seeking relaxation and entertainment. Many of these properties offer a range of amenities, including private pools, hot tubs, outdoor dining areas, and fully equipped kitchens, superb for both unwinding and hosting gatherings. Find your rental in Old Town Key West with a pool or a hot tub.
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.
Are there pet-friendly vacation rentals in Old Town Key West?
Yes, you can book pet-friendly vacation rentals in Old Town Key West, where you'll find a variety of options to choose from. This lively area is known for its vibrant atmosphere, historic architecture, and proximity to beautiful beaches. Many vacation rentals here come equipped with amenities such as private patios, outdoor seating areas, and fully stocked kitchens, making them comfortable for both you and your pet.

Old Town Key West is also close to several pet-friendly points of interest. The nearby Fort Zachary Taylor Historic State Park features sandy beaches where pets are allowed on leashes, providing a great spot for walks and picnics. See all pet-friendly rentals in Old Town Key West.
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 among travelers. This vibrant period attracts those looking for a lively escape, as visitors flock to enjoy the beautiful beaches, clear blue waters, and a lot of outdoor activities such as snorkeling, fishing, and exploring the historic architecture.

During these months, you can expect warm temperatures ranging from the mid-60s to mid-80s Fahrenheit, ideal for those who relish sunbathing or enjoying leisurely strolls through the charming streets filled with colorful buildings and lush gardens. The atmosphere is buzzing with energy, especially as many local events and festivals occur, including the renowned Fantasy Fest in late October, which is another excellent time for those seeking a great experience.

For travelers seeking a more budget-friendly option, consider planning your visit in October.
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 1,111 properties suiting this need. Travelers can expect a variety of amenities designed to facilitate productivity, including high-speed Wi-Fi, dedicated office spaces, desks, and ergonomic chairs. Many rentals also feature laptop workspaces and some even come equipped with computer monitors and safes for secure storage of valuables.

The charming streets of Old Town are lined with historical sites, vibrant nightlife, and local eateries, providing a great balance between work and leisure. After a productive day, you can unwind by exploring nearby attractions such as the Ernest Hemingway Home and Museum or enjoying the sunset at Mallory Square. 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?
In Old Town Key West, visitors can experience firsthand a vibrant atmosphere filled with historical charm and tropical beauty. The iconic Duval Street is a must-visit, offering a lively scene with numerous bars, restaurants, and shops, making it superb for vacation rentals nearby that provide easy access to the action. The Ernest Hemingway Home and Museum is located in the area, showcasing the author's former residence and beautiful gardens, while the nearby Key West Lighthouse offers panoramic views of the island.

For those interested in the arts, the Old Town area is home to various galleries and performance venues, including the historic Red Barn Theatre. Additionally, the Southernmost Point Buoy, a popular photo spot, is just a short stroll away, along with the picturesque waterfront parks like Mallory Square, known for its stunning sunsets and lively street performances.
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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