Key West Historic District holiday lettings

We found 1,766 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Key West Historic District by choosing from 758 houses, 238 apartments and other holiday rentals. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a fireplace. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including accessible or non-smoking choices.

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Frequently asked questions

What is the most popular type of holiday rental in Key West Historic District?
In the Key West Historic District, holiday houses are the most prevalent type of rental, with around 192 options available. These charming properties are typically situated in historic neighbourhoods, close to attractions such as the Ernest Hemingway Home and Museum and the vibrant Duval Street. Most holiday houses come equipped with multiple bedrooms, fully equipped kitchens, and inviting outdoor spaces like patios or porches, superb for enjoying the warm Florida evenings.
Are there any beach house rentals in Key West Historic District?
In the Key West Historic District, there are approximately 678 beach house holiday rentals available. These charming properties are typically situated in picturesque neighbourhoods, close to iconic landmarks such as the Ernest Hemingway Home and Museum and the lively Duval Street. Travellers can expect a variety of amenities, including fully equipped kitchens, spacious living areas, and often private outdoor spaces such as patios or balconies where they can relax and enjoy the tropical atmosphere. Many rentals also feature amenities like swimming pools, hot tubs, and easy access to the beach, making them ideal for families and groups looking for a memorable seaside getaway.
How much does it cost to rent a holiday home in Key West Historic District?
Prices for holiday rentals in Key West Historic District 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 Key West Historic District 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 Key West Historic District holiday house rentals?
You can find great discounts on house rentals in Key West Historic District 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 Key West Historic District holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Key West Historic District 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 Key West Historic District?
A long-stay holiday rental in Key West Historic District 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 Key West Historic District for a holiday rental?
The peak season for visiting the Key West Historic District runs from May to July, with July being the most popular month. This vibrant period attracts holidaymakers eager to soak up the sun, enjoy water sports, and explore the rich history of this charming area. With temperatures averaging around 30°C, the warm weather creates a friendly space for outdoor adventures, from snorkelling in the crystal-clear waters to wandering through the historic streets lined with colourful Victorian homes.

While the summer months are bustling with tourists, those seeking a quieter experience might consider visiting in October. Although this is generally regarded as the low season, October offers pleasant temperatures in the mid to high 20s Celsius, making it comfortable for sightseeing and leisurely strolls along the famous Duval Street. Additionally, the lower tourist numbers mean you can enjoy a more relaxed pace as you explore the local shops, galleries, and eateries.
Are there any remote work holiday rentals in Key West Historic District?
In the Key West Historic District, there are numerous remote work holiday rentals available, specifically around 331 options to choose from. This vibrant area, known for its rich history and charming architecture, provides an excellent backdrop for those looking to combine work and leisure. Many of the properties come equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated desks, and comfortable office chairs, ensuring a productive environment. Some rentals even feature additional perks such as laptop workspaces and computer monitors, making it easier for travellers to stay connected. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Key West Historic District holiday rental?
Book your Key West Historic District 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 Key West Historic District?
In the Key West Historic District, visitors can take part in a rich tapestry of attractions. The Ernest Hemingway Home and Museum offers a glimpse into the life of the renowned author, while the nearby Key West Lighthouse provides panoramic views of the island. Strolling down Duval Street, holiday rentals provide easy access to a variety of shops, bars, and restaurants that capture the vibrant spirit of the area.
Can I change or cancel my Key West Historic District home rental booking on Vrbo?
To find Key West Historic District 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 Key West Historic District 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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