Old Town Key West holiday lettings

We found 1,572 holiday rentals — enter your dates for availability
Select from 552 houses, 251 flats and other holiday rentals to find the perfect place for your stay in Old Town Key West. Whether you’re staying in a holiday home with family or friends, you'll have the amenities that you expect and more, such as parking and air conditioning. Whatever you're looking for, you're sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Find spaces that suit your style

Why visit Old Town Key West

  • Historic Landmarks: Explore iconic sites like the Ernest Hemingway Home and Museum and the Key West Lighthouse, showcasing the area's rich history.
  • Vibrant Atmosphere: Stroll through colourful streets lined with charming Victorian architecture and lively markets, capturing the essence of Key West.
  • Sunset Celebrations: Experience the famous sunset celebrations at Mallory Square, a must-see event filled with entertainment and local culture.
  • Family-Friendly Attractions: Visit the engaging Key West Aquarium for an enjoyable and educational experience suitable for all ages.
  • Beautiful Beaches: Relax on stunning beaches that offer a perfect blend of relaxation and tropical adventure.

Popular types of accommodation around Old Town Key West

Discover the charm of Old Town Key West, where colourful historic cottages and inviting guesthouses await. This vibrant neighbourhood boasts iconic landmarks, including the famous sunset celebrations at Mallory Square and the Ernest Hemingway Home and Museum. With a range of quality accommodations, from houses to cosy condos, Old Town Key West offers the perfect base for exploring its lively atmosphere, unique shops, and delectable dining options. Experience the true essence of Key West in this delightful locale.

  • Houses: Enjoy the comfort and space of Houses, the top choice for visitors seeking a home-away-from-home experience in Old Town Key West.
  • Condos: Condos offer modern amenities and a convenient base for exploring the vibrant surroundings, making them the second most sought-after option.
  • Cottages: Quaint and charming, Cottages provide a delightful retreat with a touch of local character, ranking third in popularity.
  • Apartments: Apartments combine affordability and practicality, ideal for those wanting a self-catering option in the heart of the action.
  • Villas: Luxurious Villas are perfect for those seeking an upscale getaway, offering spacious accommodations and stunning surroundings.**

Top attractions in and around Old Town Key West

Old Town Key West is a vibrant neighbourhood perfect for families, couples, and business travellers alike. Explore the stunning beaches, stroll along the lively streets, and visit the symbolic landmarks such as the Key West Lighthouse and the historic seaport. Don't miss the engaging exhibits at the Key West Aquarium, offering a delightful family experience while immersing yourself in the local culture and charm.

  • Duval Street: A vibrant thoroughfare teeming with lively bars, eclectic shops, and a bustling atmosphere, perfect for experiencing the local culture and nightlife.
  • Ernest Hemingway Home and Museum: A charming historic house where the famous author lived, showcasing his life and works amidst beautiful gardens and unique six-toed cats.
  • South Beach: A stunning stretch of sandy shoreline ideal for sunbathing, swimming, and enjoying breathtaking sunsets, embodying the quintessential beach vibes of Key West.

Things to do recommended for couples

Seeking a romantic getaway in Old Town Key West? Indulge in a sunset sail on a catamaran, wander hand-in-hand through the charming streets, or enjoy a candlelit dinner at a waterfront restaurant. Don’t miss the vibrant atmosphere of Mallory Square as the sun dips below the horizon.

Things to do recommended for families

Families will delight in the enchanting Key West Butterfly and Nature Conservatory, where colourful butterflies flutter freely, or explore the fascinating exhibits at the Mel Fisher Maritime Museum. Enjoy a leisurely stroll along the picturesque waterfront or indulge in a delicious meal at a family-friendly eatery.

Things to do recommended for groups

Groups visiting Old Town Key West can enjoy a vibrant sunset celebration at Mallory Square, explore the historic Ernest Hemingway Home and Museum, and embark on a thrilling group snorkelling adventure in the crystal-clear waters of the Florida Keys.

*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

If you're travelling with a group, with family, bringing along pets, or seeking extended stays, it's important to use the appropriate filters to meet your needs. Here are some helpful booking tips for Vrbo.

  • Traveling to Old Town Key West with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Old Town Key West with young kids: Venturing out with young children can indeed present its challenges. It's essential to prioritise their comfort and safety, along with suitable amenities, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Old Town Key West: For many families, a holiday isn’t truly fulfilled without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer 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 seeking holiday rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Old Town Key West

Old Town Key West is a vibrant neighbourhood steeped in history and charm, perfect for a memorable holiday. Visitors can explore iconic landmarks like the Ernest Hemingway Home and Museum, stroll along the picturesque streets lined with colourful Victorian architecture, and enjoy the lively atmosphere of local markets and cafés. With its tropical vibe and rich cultural heritage, Old Town Key West offers an engaging blend of relaxation and adventure for every traveller.

  • Key West: Key West is a vibrant city situated on the southernmost point of the continental United States, characterized by its picturesque island setting. Visitors flock to Key West for its unique blend of family-friendly activities, business ventures, and city-themed experiences. The area boasts an array of attractions including stunning beaches, shopping areas, and lively resorts. Here, you can explore the iconic Duval Street, known for its nightlife, restaurants, and eclectic shops. The beautiful beaches and family-friendly areas provide plenty of opportunities for relaxation and adventure.
  • Key West Historic District: Located a mere 483m from Old Town Key West, the Key West Historic District is a charming neighbourhood that showcases the island's rich history and architecture. Travellers are drawn to this area for its city-themed and family-friendly experiences, with an abundance of shopping areas and resorts nearby. As you stroll through the district, you'll encounter beautiful historic homes, quaint streets, and local landmarks that reflect the unique culture of Key West. The proximity to beaches makes it an ideal spot for a leisurely day out.
  • Downtown Key West: Just 322m from Old Town Key West, Downtown Key West is a lively neighbourhood brimming with activities for families, tourists, and business travellers alike. This area features an assortment of shopping malls and local boutiques, as well as resorts that cater to diverse tastes. Visitors can enjoy the vibrant street life, with an array of restaurants and cafés, while the nearby beaches provide a perfect escape for sun-seekers and families. A blend of culture, history, and coastal charm awaits you in Downtown Key West.

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 iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to refine your search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a dedicated space for you to create new journeys, refine your travel plans, or manage your bookings effectively. Your saved or reserved properties are conveniently categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

How much does it cost to rent a holiday home in Old Town Key West?
Prices for holiday 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 holiday 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.
Are there any Old Town Key West holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Old Town Key West with parking available—perfect for families or travellers 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 find long-stay holiday rentals in Old Town Key West?
A long-stay holiday rental in Old Town Key West is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Old Town Key West for a holiday rental?
The best time to visit Old Town Key West for a holiday rental is during the peak season from January to March, with March being particularly popular among travellers seeking vibrant experiences and sunny weather. This period welcomes visitors eager to soak up the lively option, enjoy the beautiful beaches, and partake in various water sports. Expect comfortable temperatures averaging between 20 to 28 degrees Celsius, making it ideal for outdoor activities and leisurely strolls through the historic streets.

During these months, you'll find a lot of events and activities, from lively street festivals to sunset celebrations at Mallory Square. The bustling atmosphere is complemented by a variety of dining options and live music, ensuring there's never a dull moment.

For those looking for more budget-friendly options, consider visiting in October. While this is the low season, it offers a more relaxed experience with fewer crowds. You can enjoy the tranquil beauty of the island, explore local attractions without the hustle and bustle, and still revel in the warm temperatures.
How early should I book a Old Town Key West holiday rental?
Book your Old Town Key West holiday 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 holiday 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 immerse themselves in a range of captivating attractions. The iconic Mallory Square is a must-visit, known for its vibrant sunset celebrations, where street performers and local artisans gather to create a lively option. Just a short stroll away, you'll find the Ernest Hemingway Home and Museum, offering a glimpse into the life of the famous author amidst lush gardens and historic architecture.

Duval Street is another highlight, bustling with shops, bars, and restaurants that showcase the island's lively culture. For those interested in history, the Key West Lighthouse and Keeper's Quarters Museum provides stunning views and insight into the island's maritime heritage. Additionally, the Southernmost Point Buoy, marking the southernmost tip of the continental United States, is a popular photo stop for visitors.

Nature enthusiasts can explore the nearby Dry Tortugas National Park, accessible by ferry, where stunning beaches and historic Fort Jefferson await.
Can I change or cancel my Old Town Key West home rental booking on Vrbo?
To find Old Town Key West holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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