Old Town Key West holiday homes

We found 1,535 holiday rentals — enter your dates for availability
Select from 560 houses, 243 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

    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, 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

What is the most popular type of holiday home accommodation in Old Town Key West?
Houses are the most popular type of holiday home in Old Town Key West, according to our data. Even if you've got something different in mind, Bookabach has properties in loads of sizes and shapes. Browse our many options to find your perfect Old Town Key West pad.
How much does it cost to rent a holiday home in Old Town Key West?
Season, length of stay and property type are some factors that can affect the price of a holiday home. Simply enter your dates of travel to find your ideal fit. From comfy cabins to plush villas, all Bookabach holiday homes provide incredible value.
How much does it cost to rent a beach house in Old Town Key West?
The average price for a holiday home by the beach in Old Town Key West depends on when you're going and the size and style of property you're searching for. Find prices easily on Bookabach by entering your destination and preferred travel dates. Then make use of the filter tool to choose the number of bedrooms and amenities that you prefer, such as WiFi, a pool and air conditioning.
Are there pet-friendly holiday homes in Old Town Key West?
With 1,312 holiday homes that allow pets, your little buddy can join in on your Old Town Key West holiday. Use our filter tool to search our pet-friendly holiday homes and find a stay that'll set tails wagging on Bookabach.
Can I rent a house with a pool in Old Town Key West?
Add another level of fun to your trip by booking your group into one of the 1,057 houses with a private pool in Old Town Key West. Use our search filter to find properties with pools on Bookabach, then spend carefree days playing and splashing in a swimming pool that's for your exclusive use.
What are popular home amenities in Old Town Key West?
When it comes to home amenities that people look for in Old Town Key West, a barbecue grill, a chef and mountain views rank highest. With Bookabach holiday homes, you'll enjoy choices to suit your style and taste, whether you're going away with your partner, your family or even pets.
Are there large group holiday homes in Old Town Key West?
Old Town Key West has 100 holiday properties that can accommodate 10 or more guests. These properties come with the space and privacy you need to share good times with family and friends.
Are there holiday homes in Old Town Key West that welcome kids?
With 1,307 family-friendly holiday homes available in Old Town Key West, now is a superb time to introduce your little ones to the thrills of travel. Just check our "Properties good for families" filter to search for stays that come with conveniences ideal for travelling families, such as living rooms, swimming pools, bunk beds and hot tubs.
What are the top attractions for families in Old Town Key West?
There are tons of wonderful things to see and do with the family in Old Town Key West, such as:
  • Smathers Beach
  • South Beach
  • Higgs Beach
Are there one-bedroom holiday homes in Old Town Key West?
Yes, you can pick from 359 one-bedroom homes in Old Town Key West. Whether you're on the lookout for a cosy chalet or an upmarket condo, our one-bedroom homes are great if you don't require huge amounts of space. One of the best things about having your own pad? You won't ever need to share your trip with strangers.
Can I find two-bedroom holiday homes in Old Town Key West?
Choose from 500 two-bedroom homes in Old Town Key West. Settle the kids into the second room or maybe fill it with a couple of your best buddies. There's ample space for whoever's lucky enough to come along for the ride.
Are there holiday homes with WiFi in Old Town Key West?
Old Town Key West has 413 holiday homes with WiFi, so you'll be able to stay connected while on holiday. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with the family to posting pics on social media, these Bookabach homes make it a cinch to go online.
How can I find holiday homes with air conditioning in Old Town Key West?
You can choose from 1,266 holiday homes with air conditioning in Old Town Key West offering that gentle, cool breeze and extra level of comfort. Simply enter your preferred travel dates and then use our handy filter tool to look for properties with air conditioning.
How old do you have to be to rent a holiday home in Old Town Key West?
We recommend you check with the Old Town Key West holiday property you're looking at on Bookabach as the minimum age varies. However, generally it's 16, 18 or 21.
How long can I rent a holiday home in Old Town Key West for?
How long you can book a holiday home in Old Town Key West is up to the property. Just enter your chosen travel dates to view a list of options offering extended stays. With loads of creature comforts such as full kitchens and air conditioning, as well as some offering weekly or monthly discounts, you're sure to get somewhere perfect to call your home away from home in Old Town Key West.

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