Key West Historic District vacation rentals

We found 1,767 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Key West Historic District by choosing from 758 houses, 238 apartments, and other vacation rentals. Whether you’re staying in a vacation home with family, friends, or just your furry companion, you'll have the best amenities for spending time at your home away from home, which might include parking and a hot tub. Whatever you're looking for, you'll be sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

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Find out more about Key West Historic District

Why visit Key West Historic District

  1. Rich history: The Key West Historic District boasts captivating historic houses and museums that showcase the area's unique heritage.
  2. Charming streets: Wander through Old Town Key West's vibrant and picturesque streets, perfect for leisurely strolls and exploration.
  3. Tropical atmosphere: Enjoy a relaxing beach vibe while immersing yourself in the local culture and community.
  4. Diverse accommodations: Choose from charming vacation homes, modern condos, and delightful cottages to enhance your stay.
  5. Family-friendly activities: The district offers engaging excursions and attractions suitable for visitors of all ages.

Popular types of accommodation around Key West Historic District

If you're seeking the perfect getaway in the Key West Historic District, look no further. Our top choices for vacation rentals include charming Houses, modern Condos, and delightful Cottages. Enjoy a blend of historic charm and modernized amenities, ensuring your stay is both comfortable and memorable. Whether you’re looking for the ultimate Key West accommodations or a cozy retreat near the Gates Hotel, we’ve got the ideal spot for you.

  • Houses: The top choice for visitors, these spacious homes provide a comfortable and cozy environment for families or groups in Key West Historic District.
  • Condos: A popular option for those seeking modern amenities and stunning views, condos offer a convenient stay in the heart of Key West.
  • Cottages: Charming and quaint, cottages provide a unique and intimate atmosphere for a delightful getaway.
  • Apartments: Ideal for solo travellers or couples, apartments offer flexibility and easy access to local attractions.
  • Caravan Parks: For a more rustic experience, caravan parks are perfect for those looking to enjoy the great outdoors while staying close to the action.**

Top attractions around Key West Historic District

The Key West Historic District is perfect for family getaways or business trips, offering a rich blend of historic houses, vibrant streets, and engaging museums. Visitors can immerse themselves in the local culture while enjoying the beach atmosphere. Explore the area's fascinating historic sites and take part in a fun-filled afternoon in Key West to enhance your vacation experience.

  1. Duval Street: Experience the vibrant heart of Key West with lively shops, restaurants, and bars lining this iconic street. It's a perfect blend of local culture and tourist excitement, making it a must-visit for a taste of the city vibe.
  2. Mallory Square: A bustling modern square famous for its sunset celebrations, street performers, and local artisans. The lively atmosphere here is ideal for soaking in the unique culture and charm of Key West.
  3. Ernest Hemingway Home and Museum: Discover the rich literary history of this historic house where the renowned author lived. Explore the lush gardens and learn about Hemingway’s life, offering a deep cultural experience in a serene setting.

Things to do recommended for families

Families visiting Key West can splash around at the MLK Community Pool & Community Center, located 966m from the Historic District. This inviting spot offers a family-friendly atmosphere with outdoor vibes, perfect for a fun day of swimming and relaxation.

Things to do recommended for groups

Experience the charm of Key West with your group at the Waterfront Playhouse for a night of entertainment, then shop at The Kite House for unique souvenirs. For a bit of sport, enjoy a round at the Key West Golf Club, just 6.4km away.

What do I need to keep in mind when booking a vacation around Key West Historic District

If you're planning a trip with a group, family, or pets, or if you're seeking extended stays, be sure to use the appropriate filters to align with your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Key West Historic District with a group: Think about how many bedrooms you require, along with amenities like a full kitchen or outdoor space for gatherings. Luckily, you can easily apply filters for all of these options and more on Vrbo.
  • Traveling to Key West Historic District with young kids: Travelling with young children can be quite demanding. It’s important to prioritize 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 Key West Historic District: For many, a family getaway isn’t truly fulfilling without their furry companion by their side. If that resonates with you, consider exploring Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Key West Historic District: If you're seeking vacation 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 rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay around Key West Historic District

Exploring the Key West Historic District offers a vibrant mix of adventure and history, perfect for families and business travellers alike. Immerse yourself in the tropical atmosphere as you wander through Old Town Key West's charming streets and historic neighbourhoods. Discover fascinating excursions that showcase the area's rich heritage, making your vacation a memorable experience. Whether you're here for relaxation or exploration, Key West's unique vibe will leave you enchanted.

  • Old Town Key West: Old Town Key West is a charming neighborhood located a mere 483m from the Key West Historic District. Known for its vibrant atmosphere, this area offers a delightful blend of city, family, and business experiences. Visitors can explore popular shopping areas and a variety of resorts, making it a great place for both relaxation and adventure. The local attractions include picturesque streets and beautiful family-friendly beaches, providing ample opportunities for leisurely strolls and fun in the sun. Old Town's unique character and historic charm make it a must-visit destination.
  • Downtown Key West: Also situated 483m from the Key West Historic District, Downtown Key West buzzes with activity and excitement. This neighbourhood is ideal for families, professionals, and tourists alike, with numerous shopping areas and resort options to choose from. Visitors can enjoy the vibrant street life and unwind at nearby beaches that cater to families. Downtown Key West encapsulates the essence of island living, offering a fantastic blend of relaxation and entertainment, making it an essential stop on your vacation.
  • Historic Seaport: Located just 644m from the Key West Historic District, Historic Seaport is a picturesque neighbourhood that embodies the maritime charm of the area. Here, you can experience a variety of city, family, and business activities. The seaport features bustling shopping areas and a selection of resorts, while local attractions include scenic streets and a marina perfect for boating enthusiasts. With its lively atmosphere and stunning waterfront views, Historic Seaport presents an unforgettable travel experience for visitors looking to immerse themselves in the rich history and beauty of Key West.

Best time to go to Key West Historic District

If you're planning a trip to Key West Historic District, 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

Are you hoping to save on your next adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking a longer stay can lead to considerable savings. To discover a Vrbo property that suits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers an easy-to-use platform for planning your travel adventures. You can create new trips, resume your previous plans, or review and organise your itinerary all in one place. The properties you’ve saved or booked are clearly sorted into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Key West Historic District?
In the Key West Historic District, vacation houses are the most popular rental option, with around 192 available throughout the area. These charming properties often feature traditional architecture and offer visitors a quintessential Key West experience. Most houses come equipped with fully stocked kitchens, spacious living areas, and outdoor patios or gardens, great for enjoying the warm Florida evenings.

Additionally, there are about 88 apartments, which cater to those looking for a more compact accommodation. These typically include amenities such as kitchenettes, comfortable sitting areas, and access to shared facilities like pools. For those preferring a unique stay, approximately 49 condos are also available, often providing resort-style amenities alongside private balconies for enjoying the island's beautiful sunsets.
Are there any beach house rentals in Key West Historic District?
In the Key West Historic District, there are approximately 678 beach house rentals available, making it a popular destination for visitors seeking a coastal getaway. These beach houses are typically located within walking distance of iconic attractions such as the Ernest Hemingway Home and Museum, the vibrant Duval Street, and the picturesque waterfront.
How much does it cost to rent a vacation home in Key West Historic District?
Prices for vacation 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 travelling 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.
Are there any discounts for Key West Historic District vacation 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 vacation rentals with parking?
Vrbo offers a wide selection of vacation 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 vacation rentals in Key West Historic District?
A long-stay vacation 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 vacation rental?
The most popular time to visit the Key West Historic District is during the peak season, which runs from May to July. This vibrant period attracts travellers eager to soak up the sun, enjoy water sports, and explore the rich history of the area. With warm temperatures averaging around 30°C, the weather is superb for outdoor activities such as snorkelling, diving, or simply lounging by the beach.

July stands out as the most sought-after month, drawing in crowds for its lively atmosphere and numerous summer events. Visitors can take advantage of the long days to explore the charming streets, visit historic sites like the Ernest Hemingway Home and Museum, or indulge in fresh seafood at local restaurants.

For those looking for a more budget-conscious option, October offers a wonderful opportunity to experience Key West at a slower pace. With fewer tourists around, you can enjoy the beauty of the island's natural surroundings and partake in the local culture without the crowds. The weather remains pleasant, with temperatures in the mid-20s Celsius, making it ideal for leisurely strolls and scenic bike rides.
Are there any remote work vacation rentals in Key West Historic District?
In the Key West Historic District, there are numerous remote work-friendly vacation rentals available, with around 331 options to choose from. This vibrant area, known for its historic charm, offers properties that cater to those needing to balance work and leisure. Many rentals feature dedicated workspaces, including desks and ergonomic chairs, ensuring a comfortable environment for productivity. Additionally, amenities like Wi-Fi, computer monitors, and safes are often included, providing a seamless working experience while enjoying the tropical surroundings. 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 vacation rental?
Book your Key West Historic District 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 Key West Historic District?
In the Key West Historic District, visitors can experience firsthand a rich tapestry of attractions. The district is home to the iconic Ernest Hemingway Home and Museum, where fans of literature can explore the house and gardens that once belonged to the famous author. Nearby, the lively Duval Street offers a mix of shops, bars, and restaurants, making it a bustling hub for both tourists and locals.

Another highlight is the Southernmost Point Buoy, a popular photo spot that marks the southernmost point of the continental United States. For those interested in history, the Key West Lighthouse and Keeper's Quarters Museum provides a glimpse into the island's maritime past, while the nearby Fort Zachary Taylor Historic State Park offers both historical insights and beautiful beach access.
Can I change or cancel my Key West Historic District home rental booking on Vrbo?
To find Key West Historic District 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 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 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.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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