Old Town Key West vacation rentals

We found 1,610 vacation rentals — enter your dates for availability

Select from 623 houses, 272 condos, and other vacation rentals to find the perfect place for your stay in Old Town Key West. Whether you’re staying in a vacation home with a group or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include a hot tub and a washer and dryer. Whatever you're looking for, you'll find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Old Town Key West

Showing deals for:Jan 30 - Feb 6

Image gallery for 1 Block to Duval St | Banana's Foster Guesthouse

Plunge pool and courtyard
10 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)

1 Block to Duval St | Banana's Foster Guesthouse

Key West, FL

10% off
Price is CA $3,730
CA $32,904 total
includes taxes & fees
1 Block to Duval St | Banana's Foster Guesthouse

Find spaces that suit your style

Find out more about Old Town Key West

Why visit Old Town Key West

  • Historic District: Wander through the picturesque streets of the Key West Historic District, rich in culture and charm.
  • Local Cuisine: Enjoy fresh seafood and vibrant dining options at local eateries, perfect for food lovers.
  • Unique Attractions: Discover symbolic landmarks and attractions that showcase Key West's historical significance.
  • Tropical Ambiance: Experience the tropical charm of beautiful beaches and vibrant streets, ideal for relaxation.
  • Diverse Accommodation: Choose from cozy cottages to stylish condos, catering to all vacation styles and budgets.

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 find the perfect accommodation. Whether you're looking for houses, cozy cottages, or stylish condos, there's something for everyone. Discover the charm of Key West hotels and town resorts that cater to your needs, all while enjoying the savings and reassurance you deserve. Explore your options on our platform to make your vacation truly memorable.

  • Houses: The top choice for visitors to Old Town Key West, these homes offer spacious and comfortable settings ideal for families or groups.
  • Condos: A close second, condos provide modern amenities and often stunning views, perfect for enjoying the vibrant atmosphere of the area.
  • Cottages: These charming retreats offer a cozy, intimate vibe and are perfect for couples seeking a romantic getaway.
  • Apartments: A practical option for solo travellers or couples, apartments deliver convenience and accessibility to local attractions.
  • Villas: Offering luxury and expansive spaces, villas are a wonderful choice for those wanting a lavish stay in Key West.**

Top attractions in and around Old Town Key West

Old Town Key West offers a variety of attractions perfect for family vacations, business trips, or city-themed getaways. Visitors can explore stunning beaches, vibrant streets, and symbolic landmarks, all while enjoying the rich culture and unique city experience. Don't miss out on the many tours and key attractions that showcase the charm of this historic area, making it an ideal destination for travellers seeking adventure and relaxation alike.

  • Duval Street: This vibrant street is the heart of Key West, brimming with lively bars, eclectic shops, and fantastic dining options. Stroll along to soak in the energetic atmosphere and enjoy local art and performances.
  • Southernmost Point: A must-see landmark, this buoy marks the southernmost point in the continental U.S. Capture a quintessential photo while immersing yourself in the local culture and stunning ocean views.
  • Ernest Hemingway Home and Museum: Explore the former residence of the legendary author, featuring beautiful gardens and fascinating insights into his life and work. A true cultural gem in 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 crystal-clear waters, or savour a candlelit dinner at a cozy bistro. Each moment together will create lasting memories in this tropical paradise.

Things to do recommended for families

Families visiting Old Town Key West can enjoy splashing fun at the MLK Community Pool, where kids can swim and play in a vibrant outdoor setting. The community centre also offers various sports activities, perfect for a day of family bonding and adventure.

Things to do recommended for groups

Enjoy a round of golf at the Key West Golf Club, only 6.4km from Old Town. Catch a show at the charming Red Barn Theater, just 966m away, or explore the unique offerings at The Kite House right in Old Town for a truly local experience.

*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

If you're planning a trip with a group, enjoying a family getaway, traveling with pets, or seeking longer accommodations, it's important to prioritize your preferences. Here are some helpful booking tips for using Vrbo.

  • Traveling to Old Town Key West with a group: Think about how many bedrooms you require, as well as features like a complete kitchen or outdoor space for group gatherings. Thankfully, Vrbo allows you to filter for these options and much more.
  • Traveling to Old Town Key West with young kids: Traveling with young kids 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 attractions that are enjoyable for families.
  • Taking your pets with you to Old Town Key West: For many families, a trip isn't truly complete without their furry companion. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and pet 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 vacation rentals offering discounts 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 preferences like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Old Town Key West

Old Town Key West offers a delightful blend of tropical charm and rich history, making it an ideal destination for families and adventurers alike. Stroll through the picturesque streets of the Key West Historic District, explore local boutiques, and savour fresh seafood at vibrant eateries. With its unique atmosphere, Old Town Key West invites visitors to immerse themselves in its lively excursions and exceptional experiences, ensuring a memorable vacation in this enchanting Florida locale.

  • Key West: Nestled on a picturesque island, Key West is a vibrant city known for its laid-back charm and year-round sunshine. This tropical paradise is a popular destination for families and business travellers alike, offering a plethora of attractions. Visitors can enjoy sandy beaches and family-friendly waterfronts, while the bustling shopping areas and mall centres provide ample opportunities for retail therapy. Key West is also renowned for its stunning sunsets, making it a fantastic spot for leisurely strolls along the shore.
  • Key West Historic District: Located a mere 483m from Old Town Key West, the Key West Historic District is a delightful neighbourhood steeped in rich history. This area is perfect for those seeking a blend of culture and relaxation. Stroll through charming streets lined with historic homes and enjoy the local shops and markets. With beautiful beaches nearby, families can easily spend a day soaking up the sun. The Historic District is a haven for those wanting to experience the authentic spirit of Key West.
  • Downtown Key West: Just 322m from Old Town Key West, Downtown Key West is the bustling hub of activity. This vibrant neighbourhood is filled with an array of shops, restaurants, and entertainment venues, making it ideal for families and business travellers. Visitors can explore local boutiques, dine at waterfront restaurants, and enjoy live performances. With close proximity to beautiful beaches, Downtown Key West offers a perfect mix of relaxation and excitement, ensuring an unforgettable travel experience.

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

Planning your next getaway and hoping to save some money? Being flexible with your travel dates can make a big difference, as prices can fluctuate. Additionally, consider booking an extended stay to unlock even more substantial 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 spot for your trip.

Vrbo Trips: Planning as easy as it gets

Vrbo's unique Trip Board offers you a convenient way to plan your journeys. You can initiate new trips, pick up right where you left off, or easily view and organize your travel plans. The properties you've saved and booked are now neatly arranged under Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply 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 Old Town Key West?
In Old Town Key West, vacation houses are the predominant type of rental, with approximately 639 available throughout the area. These properties often feature spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor spaces such as gardens or patios, making them ideal for families or groups. Many vacation houses are located near popular attractions like the Ernest Hemingway Home and Museum and the lively Duval Street, allowing guests to easily explore the vibrant local culture.
Are there any beach house rentals in Old Town Key West?
In Old Town Key West, there is a substantial selection of beach house rentals, with approximately 1,424 available. These beach houses are primarily located in charming neighbourhoods close to iconic attractions such as the Ernest Hemingway Home and Museum, the lively Duval Street, and the picturesque waterfront. Most beach houses come equipped with modern amenities, including spacious living areas, fully stocked kitchens, private pools, and outdoor decks, making them ideal for families and groups looking to enjoy the sunny Florida lifestyle. The proximity to the beach and local attractions enhances the appeal, providing guests with both comfort and convenience during their stay.
How much does it cost to rent a vacation home in Old Town Key West?
Prices for vacation 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 travelling 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.
Are there any discounts for Old Town Key West vacation 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 vacation rentals with parking?
Vrbo offers a wide selection of vacation 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 vacation rentals in Old Town Key West?
A long-stay vacation 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 vacation rental?
March is the most popular time to visit Old Town Key West, making it an ideal choice for travellers seeking vibrant experiences in this charming destination. The peak season runs from January to March, attracting visitors who revel in the lively atmosphere, great weather, and a lot of outdoor activities. With temperatures typically ranging from the mid to high 20s Celsius, you can comfortably explore the historic streets, indulge in water sports, or simply relax on the sun-kissed beaches.

During this bustling time, you'll find a variety of events, including festivals and live music, which add to the unique character of Old Town. The captivating sunset celebrations at Mallory Square are not to be missed, offering an enchanting backdrop for your holiday.

If you're looking for a more budget-friendly option, consider visiting in October. While this month is generally quieter, it offers a chance to experience the local culture without the crowds, and you can enjoy pleasant temperatures in the low 30s Celsius. This is a great time for leisurely strolls, discovering local eateries, or taking part in fishing charters, all while soaking in the charm of Key West.
Are there any remote work vacation rentals in Old Town Key West?
In Old Town Key West, there is a wealth of options for remote work vacation rentals, with around 1,116 available in the area. This vibrant neighbourhood is known for its lively atmosphere, historical charm, and proximity to stunning beaches. Properties here often come equipped with essential amenities for remote workers, including dedicated desk spaces, high-speed Wi-Fi, and comfortable office chairs, allowing you to stay productive while enjoying your holiday. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Old Town Key West vacation rental?
Book your Old Town Key West 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 Old Town Key West?
In Old Town Key West, visitors can experience firsthand a vibrant mix of attractions and charming streets. The famous Duval Street is a lively hub, known for its lively shops, bars, and restaurants, making it an ideal area for vacation rentals. Nearby, the Ernest Hemingway Home and Museum offers a glimpse into the life of the celebrated author, while the stunning sunsets at Mallory Square provide a daily spectacle worth experiencing.
Can I change or cancel my Old Town Key West home rental booking on Vrbo?
To find Old Town Key West 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Old Town Key West 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.

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