Uptown - Upper Duval holiday lettings

We found 400 holiday rentals — enter your dates for availability

Select from 112 houses, 33 flats and other holiday rentals to find the perfect place for your stay in Uptown - Upper Duval. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll find the best amenities for hanging out with the people that matter most, including Wi-Fi and parking. Whatever you're looking for, you'll be able to choose a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • 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, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday rental in Uptown - Upper Duval?
In Uptown - Upper Duval, condos are the most popular type of holiday rental, with around 26 available in this lively area. These condos typically feature modern amenities such as fully equipped kitchens, spacious living areas, and outdoor balconies or patios, making them ideal for enjoying the warm Florida weather. Many are situated close to popular attractions like the vibrant nightlife of Duval Street and nearby beaches.
Are there any beach house rentals in Uptown - Upper Duval?
In Uptown - Upper Duval, Florida, there are approximately 46 beach house rentals available, suiting a variety of preferences. These properties are predominantly located in vibrant neighbourhoods, close to the lively atmosphere of Duval Street and within walking distance of stunning beaches.
How much does it cost to rent a holiday home in Uptown - Upper Duval?
Prices for holiday rentals in Uptown - Upper Duval 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 Uptown - Upper Duval 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 Uptown - Upper Duval holiday house rentals?
You can find great discounts on house rentals in Uptown - Upper Duval 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 Uptown - Upper Duval?
In Uptown - Upper Duval, popular rental amenities typically include heated pools, fully equipped kitchens, and private patios, making these properties ideal for relaxation and entertaining. Many rentals also feature shared pools, allowing guests to enjoy a communal swimming experience while soaking up the sunny Florida weather. Decks or patios are common as well, offering outdoor spaces to unwind after a day of exploring the vibrant neighbourhood, which is known for its lively atmosphere and proximity to local attractions.
Are there any family house rentals in Uptown - Upper Duval?
In the Uptown - Upper Duval area of Key West, there are numerous family-friendly house rentals available—around 25 in total. This vibrant neighbourhood is not only known for its lively atmosphere but also offers easy access to beautiful beaches and attractions suitable for all ages. Many of these homes come equipped with spacious living areas, fully stocked kitchens for preparing family meals, and outdoor spaces where children can enjoy themselves.
Can I rent a holiday home with a pool or hot tub in Uptown - Upper Duval?
In Uptown - Upper Duval, Florida, there are ample holiday homes available for rent that feature both pools and hot tubs, with around 32 options for properties with pools and 23 with hot tubs. This vibrant area is known for its lively atmosphere and proximity to local attractions, making it an excellent choice for travellers seeking relaxation and entertainment. Many of these rentals offer amenities such as private pools, inviting hot tubs, spacious outdoor areas, and fully equipped kitchens, ideal for both unwinding and entertaining.
Are there any Uptown - Upper Duval holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Uptown - Upper Duval 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 Uptown - Upper Duval?
In Uptown - Upper Duval, there are several pet-friendly holiday rentals available, offering a welcoming environment for travellers with pets. The area features a mix of charming cottages and modern apartments, many of which come equipped with essential amenities such as fully furnished kitchens, private outdoor spaces, and laundry facilities, ensuring a comfortable stay.
Can I find long-stay holiday rentals in Uptown - Upper Duval?
A long-stay holiday rental in Uptown - Upper Duval 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 Uptown - Upper Duval for a holiday rental?
March is the most popular time to visit Uptown - Upper Duval, coinciding with the peak season that spans from January to March. This vibrant period attracts holidaymakers eager to bask in the Florida sunshine while enjoying the lively atmosphere of events and festivities. With average temperatures in the mid-20s Celsius, visitors can comfortably engage in outdoor activities and explore the nearby attractions, including the stunning beaches and charming local shops.

During this peak season, you'll find that Uptown offers a bustling social scene, superb for those seeking entertainment and adventure. The energy of the area is palpable, with plenty of dining options and nightlife to complement your sun-soaked days.

If you're looking for a more budget-friendly time to visit, October presents an excellent alternative. The weather is still pleasant, and the crowds are significantly smaller, allowing for a more relaxed exploration of the neighbourhood's offerings. This month is ideal for those wanting to enjoy the local culture at a leisurely pace, perhaps discovering hidden gems that are often overlooked during the peak season.
Are there any remote work holiday rentals in Uptown - Upper Duval?
In Uptown - Upper Duval, Florida, there are numerous options for remote work holiday rentals, with approximately 48 available in the area. This vibrant neighbourhood offers a mix of charming accommodations, many of which are equipped with essential amenities to facilitate a comfortable work-from-home experience. Travellers can expect properties that feature Wi-Fi, dedicated workspaces with desks and comfortable chairs, and sometimes additional office equipment to ensure productivity during their stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Uptown - Upper Duval holiday rental?
Book your Uptown - Upper Duval 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 Uptown - Upper Duval?
In Uptown - Upper Duval, visitors can experience firsthand a vibrant atmosphere filled with unique attractions. The area is well-known for its lively nightlife and energetic shops, making it a popular destination for those seeking entertainment and local culture. The famous Duval Street runs through this neighbourhood, lined with bars, restaurants, and art galleries that capture the essence of Key West.

Nearby, the Ernest Hemingway Home and Museum offers a glimpse into the life of the iconic author, set in a beautiful historic property with lush gardens. For those who enjoy outdoor activities, the nearby Southernmost Point Buoy is a must-visit landmark, providing a superb photo opportunity and access to scenic waterfront views.
Can I change or cancel my Uptown - Upper Duval home rental booking on Vrbo?
To find Uptown - Upper Duval 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 Uptown - Upper Duval 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.

More holiday ideas