Old Town Key West holiday rentals

We found 1,556 holiday rentals — enter your dates for availability
Select from 563 houses, 249 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.

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  • More quality time

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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 Stayz?
Stayz 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?
Stayz 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 Stayz, 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 Stayz?
To find Old Town Key West holiday rentals with free cancellation, just use Stayz'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, Stayz 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 Stayz?
Stayz'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 Stayz 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. Stayz offers something for every taste and budget, from affordable homes in Old Town Key West to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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 StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz 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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