Old Town Key West holiday lettings

We found 1,604 holiday rentals — enter your dates for availability

Select from 571 houses, 257 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

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Old Town Key West

  • Rich History: Discover the intriguing heritage of Old Town Key West through its historic architecture and landmarks.
  • Vibrant Atmosphere: Stroll along lively streets filled with local shops, eateries, and cultural experiences.
  • Stunning Beaches: Relax on beautiful beaches with soft sands and inviting waters, perfect for sunbathing.
  • Local Excursions: Engage in various activities, from water sports to sightseeing tours, that highlight the area's charm.
  • Charming Accommodations: Choose from a variety of quaint cottages and vacation rentals for a unique stay.

Popular types of accommodation around Old Town Key West

You've chosen Old Town Key West for your getaway, and now it's time to select the perfect accommodation. Discover the charm of historic Key West with our range of houses, condos, and quaint cottages. Whether you're seeking a relaxing retreat or a vibrant base to explore, our Old Town Key West rentals offer a variety of options to suit every traveller's needs. Start your adventure with our selection of top-notch Key West vacation rentals.

  • Houses: The top choice for visitors to Old Town Key West, offering spacious and comfortable lodgings ideal for families or groups.
  • Condos: A popular alternative, providing modern amenities and convenient locations for those seeking a bit of luxury.
  • Cottages: Quaint and charming, these options offer a homely feel, perfect for a romantic getaway or a peaceful retreat.
  • Apartments: A practical option for those wanting self-catering facilities in a vibrant neighbourhood.
  • Villas: Elegant and spacious, villas provide an upscale experience with private pools and stunning views.**

Top attractions in and around Old Town Key West

Old Town Key West is an ideal destination for city-themed, family, or business holidays. Visitors can explore stunning beaches, vibrant streets, and iconic landmarks while immersing themselves in the local culture. Whether you're interested in sightseeing or simply enjoying the beach life, Old Town offers a delightful blend of experiences for all types of travellers. Don't miss the chance to visit this charming locale on your next adventure.

  • Duval Street: A vibrant thoroughfare teeming with energy, Duval Street is the heart of Key West, featuring charming shops, lively bars, and delightful eateries. The street is perfect for strolling, soaking up the local atmosphere, and experiencing the island's nightlife.
  • Southernmost Point: This iconic landmark marks the southernmost point in the continental USA, offering stunning ocean views and a colourful buoy for photo opportunities. It's a cultural symbol of Key West's laid-back lifestyle and maritime heritage.
  • Ernest Hemingway Home and Museum: Explore the former residence of the renowned author, where you can admire the lush gardens and historic architecture. The museum offers insights into Hemingway's life, his literary works, and the unique charm of Key West.

Things to do recommended for couples

Seeking a romantic getaway in Old Town Key West? Explore the charming streets hand-in-hand, indulge in a sunset sail on the azure waters, or savour a candlelit dinner at a quaint bistro. Don't forget to visit the picturesque Mallory Square for stunning views and lively performances.

Things to do recommended for families

Families will love the MLK Community Pool & Community Center in Old Town Key West, where they can enjoy a refreshing swim in a family-friendly atmosphere. This outdoor facility offers a perfect spot for relaxation and fun after exploring the vibrant local area.

Things to do recommended for groups

Experience the vibrant atmosphere of Old Town Key West with a round of golf at the Key West Golf Club, only 2.5km away, and enjoy a captivating show at the Key West Burlesque Theater. Don’t forget to browse unique finds at The Kite House.

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

When travelling with a group, family, pets, or seeking extended stays, it's essential to refine your search according to your key priorities. Here are some helpful Vrbo booking tips for you.

  • 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 get-togethers. Thankfully, you can easily refine your search for these and many other options on Vrbo.
  • Traveling to Old Town Key West with young kids: Travelling with young children can be quite demanding. 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, a family holiday wouldn't be the same without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Many of these 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 holiday 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 charming blend of history and tropical allure, perfect for family getaways, business retreats, or leisurely explorations. Wander the vibrant streets, where you can immerse yourself in the lively atmosphere, uncover local excursions, and indulge in adventure. With its picturesque architecture and rich heritage, Old Town Key West is a delightful destination for those seeking an unforgettable vacation experience.

  • Key West: Nestled on a picturesque island, Key West is a vibrant city located 249m from Old Town. This tropical paradise is renowned for its family-friendly atmosphere and bustling city vibe. Visitors can indulge in various activities, from shopping at local boutiques to lounging on the beach. The local landmarks include stunning sandy shores and charming streets lined with colourful houses, making it a perfect spot for a leisurely stroll. Key West's diverse resorts cater to all types of travellers, ensuring a memorable experience for families and business visitors alike.
  • Key West Historic District: Just 186m from Old Town, the Key West Historic District offers a delightful glimpse into the island's storied past. This neighbourhood is a blend of historical charm and modern conveniences, appealing to families and business travellers seeking a unique atmosphere. Visitors can explore quaint streets adorned with beautiful architecture, enjoy shopping at nearby areas, and relax on the nearby beaches. The Historic District is perfect for those looking to immerse themselves in the local culture while having access to various resorts and amenities.
  • Downtown Key West: Located a mere 124m from Old Town, Downtown Key West is the energetic core of the island. This bustling neighbourhood is popular for its lively shopping areas, delightful cafés, and local resorts, making it ideal for families and business visitors alike. The nearby beaches provide a serene escape, while the vibrant streets are filled with shops and restaurants that showcase the island's unique flair. Downtown Key West is the perfect place to experience the island's charm while enjoying modern conveniences.

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 simple

Are you hoping to save on your upcoming holiday? Being flexible with your travel dates can be beneficial, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo accommodation that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a user-friendly platform where you can easily plan new trips, resume your previous arrangements, or manage your travel itinerary. You’ll discover your saved or booked properties neatly organised under Potential, Upcoming, or Current Trips. To begin using 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.

More holiday ideas