Old Town Key West holiday homes

We found 1,536 holiday rentals — enter your dates for availability
Select from 560 houses, 247 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.

  • Peace of mind

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  • More quality time

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

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Old Town Key West

  • Cultural Heritage: Discover historic landmarks and charming streets that echo the rich heritage of Key West.
  • Iconic Seaport: Enjoy a lively seaport scene, offering an authentic taste of island life.
  • Historic Lighthouse: Experience the captivating allure of a well-preserved lighthouse.
  • Vibrant Local Atmosphere: Wander through streets lined with local eateries and unique shops.
  • Family-Friendly Adventure: Embrace a diverse, compact neighbourhood perfect for both leisure and business getaways.

Top attractions in and around Old Town Key West

Old Town Key West offers a rich blend of cultural experiences, historic landmarks, and vibrant street scenes. Visitors can explore iconic attractions such as the historic seaport, lighthouse, and aquarium, all nestled within a family-friendly and business-savvy neighbourhood. Whether you’re after a city vibe or a beach retreat, Old Town Key West provides a compact yet diverse experience that reflects the island’s unique heritage and local charm.

  • Duval Street: A vibrant street exuding city vibes, perfect for strolling, shopping, and sampling local eateries within a short distance from Old Town Key West.
  • Ernest Hemingway Home and Museum: Experience the rich cultural heritage of Key West in this historic house, where the legendary writer once lived, nestled in the heart of Old Town Key West.
  • Southernmost Point: A symbolic landmark offering a glimpse into local culture and history, marking the southern tip of Old Town Key West.

Things to do recommended for couples

For a romantic escape in Old Town Key West, enjoy a sunset sail on a catamaran, explore the charming streets hand-in-hand, or indulge in a candlelit dinner at a waterfront restaurant. Don't miss the vibrant sunsets at Mallory Square for a truly unforgettable experience.

Things to do recommended for families

Your family will love exploring the vibrant streets of Old Town Key West, visiting the interactive exhibits at the Key West Aquarium, or taking a scenic bike ride around the island. Don’t miss the sunset celebration at Mallory Square for a lively atmosphere filled with street performers.

Things to do recommended for groups

Explore the vibrant streets of Old Town Key West, tasting local seafood at bustling markets or joining a sunset sail on the turquoise waters. Visit the Ernest Hemingway Home and Museum for a touch of literary history, or enjoy a lively evening at Mallory Square with street performers and local crafts.

*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

No matter if you're journeying with mates, with your family, with your furry companions or planning an extended stay – ensure to apply the appropriate filters. Here are some Vrbo booking tips for you.

  • Traveling to Old Town Key West with a group: Think about how many bedrooms you require, as well as features like a full kitchen or outdoor area for group get-togethers. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Old Town Key West with young kids: Travelling with young kids can be quite demanding. It's important to prioritise their comfort and safety, as well as look for suitable facilities 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. If that resonates with you, take a look at Vrbo listings that welcome pets. Most pet-friendly properties 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 after holiday rentals offering long-stay deals, you've come to the right spot. With the right filters, you can effortlessly find and save on monthly rentals. Be sure to include options 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 offers a vibrant blend of history, tropical charm, and modern comforts. Wander through its quaint streets, explore historical landmarks, and soak in the lively atmosphere. Ideal for family and business getaways, this neighbourhood is a treasure trove of culture and adventure. Experience a true taste of Key West, with plenty of opportunities to enjoy local eateries and unique shops, all set against a backdrop of sun-soaked streets and rich heritage.

  • Key West, Downtown Key West, Key West Historic District: In the heart of a sun-drenched island, Key West is not only a city but a vibrant hub of family, city-themed and business experiences. Its unique geographical setting as an island offers a relaxed tropical vibe with sandy beaches and lively street scenes. Visitors can explore a variety of retail options, from bustling shopping areas to expansive shopping mall centres, and enjoy the laid-back ambience that defines this coastal paradise. The proximity of family-oriented beaches and engaging streetscapes only enhances the appeal of this destination.
  • Key West, Downtown Key West, Key West Historic District: Just a short stroll away, Downtown Key West is a charming neighbourhood brimming with city-themed, family and business experiences. Its location only 322m from Old Town Key West makes it a convenient spot for exploring the local attractions. Here, visitors can immerse themselves in the lively shopping mall centres and quaint shopping areas, while enjoying the nearby streets and family-friendly beaches. This neighbourhood perfectly blends modern retail with the historic charm of Key West.
  • Key West, Downtown Key West, Key West Historic District: A mere 483m from Old Town Key West, the Key West Historic District offers a delightful mix of city-themed, family and business experiences. The district is renowned for its rich heritage, reflected in the charming streets and close proximity to pristine beaches and family-friendly spots. With its range of shopping areas and shopping mall centres, this neighbourhood invites visitors to experience the seamless fusion of history and modernity, making it a must-visit on any holiday itinerary.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January71.1°F (21.7°C)No Rain (Dry)Mostly Sunny
February72.1°F (22.3°C)No Rain (Dry)Mostly Sunny
March73.4°F (23.0°C)No Rain (Dry)Mostly Sunny
April76.8°F (24.9°C)No Rain (Dry)Mostly Sunny
May79.3°F (26.3°C)Light RainMostly Sunny
June82.6°F (28.1°C)Light RainMostly Sunny
July84.0°F (28.9°C)Light RainMostly Sunny
August84.4°F (29.1°C)Light RainMostly Sunny
September83.7°F (28.7°C)Light RainMostly Sunny
October80.8°F (27.1°C)Light RainMostly Sunny
November76.6°F (24.8°C)Light RainMostly Sunny
December73.9°F (23.3°C)No Rain (Dry)Mostly Sunny

Booking with Vrbo is simple

Are you hoping to save on your next adventure? Being flexible with your travel dates can really make a difference, as prices often fluctuate. You can also enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient area for you to plan new adventures, refine your arrangements, or manage your bookings effectively. The properties you’ve saved or reserved are now neatly categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

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.
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.
Are all fees included in the Old Town Key West holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Old Town Key West holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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 any discounts for Old Town Key West holiday homes?
You can find great discounts on holiday homes in Old Town Key West on Bookabach, 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.
Can I change or cancel my Old Town Key West holiday home booking on Bookabach?
To find Old Town Key West holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Old Town Key West?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach'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 favourites, and build the perfect itinerary together.
How early should I book a Old Town Key West holiday home?
Book your Old Town Key West holiday home 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Old Town Key West?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Old Town Key West to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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