Downtown Key West holiday lettings

We found 825 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Downtown Key West by choosing from 72 houses, 60 apartments and other holiday rentals. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the best amenities for spending time at your holiday home, including parking and a TV. Whatever you're looking for, you'll find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Downtown Key West

Showing deals for:16 Jan - 23 Jan

Image gallery for Steps from Duval, Shared Pool - Road's End

Shared Pool & Lounge Chairs
9.6 out of 10, Exceptional, (160 reviews)
Exceptional
(160 reviews)

Steps from Duval, Shared Pool - Road's End

Key West, FL

8% off
Price is £4,022
for 7 nights, 1 apartment
£575 per night
includes taxes & fees
Steps from Duval, Shared Pool - Road's End

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Frequently asked questions

What is the most popular type of holiday rental in Downtown Key West?
In Downtown Key West, holiday houses are particularly popular, with several available in this lively area. These properties typically offer spacious layouts, including multiple bedrooms, fully equipped kitchens, and often private outdoor spaces for enjoying the warm weather. Many are situated close to the vibrant nightlife, historic sites, and the beautiful waterfront, providing easy access to attractions like Mallory Square and the Ernest Hemingway Home and Museum.
Are there any beach house rentals in Downtown Key West?
In Downtown Key West, there are about 20 beach house holiday rentals available. These charming properties are typically located within walking distance of lively attractions such as Duval Street, the Ernest Hemingway Home and Museum, and the picturesque waterfront. Most beach houses come equipped with essential amenities like fully stocked kitchens, spacious living areas, and outdoor patios or decks, ideal for enjoying the warm Florida evenings. Many also feature private pools or beach access, providing a superb setting for relaxation after a day of exploring the vibrant local culture and beautiful beaches.
How much does it cost to rent a holiday home in Downtown Key West?
Prices for holiday rentals in Downtown 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Downtown Key West 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 Downtown Key West holiday house rentals?
You can find great discounts on house rentals in Downtown 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.
What are popular rental amenities in Downtown Key West?
In Downtown Key West, holiday rentals are often equipped with a variety of popular amenities that enhance the stay for travellers. Many properties feature fully equipped kitchens, allowing guests to prepare meals and enjoy the local seafood. Additionally, heated pools are a sought-after amenity, providing a comfortable swimming experience regardless of the weather. Travellers can also expect to find patios where they can relax and enjoy the warm Florida evenings, as well as nearby access to the sea, which is great for those wanting to indulge in water activities. For a touch of convenience, coffee and tea makers are commonly available, ensuring guests can enjoy their morning brews without needing to venture out.
Are there any family house rentals in Downtown Key West?
In Downtown Key West, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. This vibrant area is known for its lively atmosphere and close proximity to key attractions such as the Southernmost Point Buoy and the bustling streets of Duval Street. Many homes in this locale offer spacious living areas, fully equipped kitchens great for family meals, and outdoor patios where kids can play or adults can unwind with a drink.
Can I rent a holiday home with a pool or hot tub in Downtown Key West?
In Downtown Key West, there are 10 holiday homes available for rent that feature pools, along with several properties offering hot tubs. This lively area is known for its vibrant atmosphere, historic architecture, and easy access to beautiful beaches. Many of the rentals come equipped with amenities such as private pools, outdoor seating areas, and fully furnished kitchens, making them ideal for relaxation and entertaining after a day of exploring the local attractions.
Are there any Downtown Key West holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Downtown 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.
Are there pet-friendly holiday rentals in Downtown Key West?
In Downtown Key West, you will find a selection of pet-friendly holiday rentals, with around 13 options available. These properties often feature amenities such as private balconies, spacious living areas, and fully equipped kitchens, making them ideal for travellers with pets seeking comfort and convenience. Many rentals are located within walking distance of the vibrant Duval Street, where guests can enjoy lively restaurants, shops, and bars.
Can I find long-stay holiday rentals in Downtown Key West?
A long-stay holiday rental in Downtown 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 Downtown Key West for a holiday rental?
March is the most popular month to visit Downtown Key West, as it falls within the peak season from January to March. During this time, the island comes alive with vibrant festivals, bustling nightlife, and an array of water-based activities that attract sun-seeking travellers. The pleasant climate, with temperatures averaging around 24-27 degrees Celsius, makes it great for outdoor adventures such as snorkelling, sailing, or simply lounging on the beautiful beaches.

For those who appreciate a lively atmosphere, visiting in March means you'll experience the excitement of events like Fantasy Fest and the famous sunset celebrations at Mallory Square, where street performers and local artisans gather. However, if you prefer a more tranquil getaway, consider planning your trip in October. This month typically sees fewer tourists, allowing you to enjoy the charm of Key West at a more leisurely pace, with the added bonus of experiencing the stunning autumn sunsets.
Are there any remote work holiday rentals in Downtown Key West?
In Downtown Key West, remote work holiday rentals are plentiful, with around 21 options available for those seeking a conducive work environment. This vibrant area is rich in history and offers a unique blend of relaxation and productivity. Many of the properties feature dedicated workspaces, such as desks and office areas, alongside essential amenities like Wi-Fi, ensuring a seamless remote working experience. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Downtown Key West holiday rental?
Book your Downtown Key West 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 Downtown Key West?
In Downtown Key West, visitors can experience firsthand a lively atmosphere filled with historical and cultural attractions. The iconic Duval Street is a must-visit, bustling with shops, bars, and restaurants. Nearby, the Ernest Hemingway Home and Museum offers a glimpse into the life of the famous author, set within lush gardens and historic architecture.

Another highlight is Mallory Square, where visitors can enjoy the famous sunset celebration, featuring street performers and local artisans. The Southernmost Point Buoy is also a popular photo spot, marking one of the southernmost points in the continental United States.
Can I change or cancel my Downtown Key West home rental booking on Vrbo?
To find Downtown Key West 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 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 Downtown Key West 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.

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