Uptown - Upper Duval holiday rentals
We found 415 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Uptown - Upper Duval by choosing from 93 houses, 30 apartments and other holiday rentals. 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.
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Find properties near top attractions in Uptown - Upper Duval

Key West Butterfly and Nature Conservatory
More information about Key West Butterfly and Nature Conservatory. Opens in a new window.Find the best place to stay - Uptown - Upper Duval

Osprey Suite | Charming Hideaway, Hot Tubs!
Sleeps 4 · 1 bedroom · 1 bathroom

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Sleeps 4 · 1 bedroom · 1 bathroom

Andy's Attic | Budget-Friendly!
Sleeps 2 · 1 bedroom · 1 bathroom

SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
Sleeps 8 · 3 bedrooms · 3 bathrooms

Sea Esta Suite | Located On Iconic Duval w/ Pool
Sleeps 6 · 2 bedrooms · 2+ bathrooms
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore 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, condominiums are the most popular type of holiday rental, with about 57 available in the area. These condos are typically situated in lively neighbourhoods, close to local attractions and the vibrant setting of the district. Most units feature modern amenities, including fully equipped kitchens, spacious living areas, and access to shared facilities such as swimming pools and fitness centres.For those seeking more space, approximately 42 holiday houses are also on offer. These properties generally come with multiple bedrooms, private outdoor areas, and often BBQ facilities, making them ideal for families or groups looking to enjoy a home-like experience. Additionally, around 27 apartments provide comfortable stays, usually equipped with essential amenities and some with balconies to enjoy the warm Floridian weather.
Are there any beach house rentals in Uptown - Upper Duval?
In Uptown - Upper Duval, there are about 38 beach house rentals available, making it a great choice for those looking to enjoy a coastal getaway. These beach houses often come equipped with modern amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces like patios or balconies for soaking up the sun. Many properties are situated close to local attractions, including vibrant nightlife, art galleries, and the beautiful beaches of Key West.
What are popular rental amenities in Uptown - Upper Duval?
In Uptown - Upper Duval, popular holiday rental amenities include fully equipped kitchens, ideal for those who prefer cooking their own meals. Many properties also feature coffee and tea makers, ensuring guests can enjoy their morning brews at their convenience. Outdoor spaces are a highlight, with numerous rentals offering decks or patios and balconies where visitors can relax and soak up the vibrant setting. Additionally, the proximity to a nearby marina enhances the appeal for those interested in water activities and exploring the local coastline.
Can I find family house rentals in Uptown - Upper Duval?
In the Uptown - Upper Duval area of Key West, there are 24 family-friendly house rentals available, making it a fantastic choice for those travelling with children. This vibrant neighbourhood is known for its lively option and proximity to attractions like the Key West Butterfly and Nature Conservatory and the historic Casa Marina.Many of these homes offer spacious living areas, fully equipped kitchens ideal for preparing family meals, and outdoor spaces where children can play or relax. Amenities such as Wi-Fi and air conditioning are typically included to ensure a comfortable stay.Additionally, the area is just a short stroll away from the beautiful beaches and local dining options, providing families with plenty to explore.
Can I rent a holiday home with a pool or hot tub in Uptown - Upper Duval?
In Uptown - Upper Duval, Florida, there are plenty of holiday homes available for rent, with around 26 properties featuring pools and 16 offering hot tubs. This vibrant neighbourhood is known for its lively option and proximity to the famous Duval Street, making it an ideal spot for travellers seeking both relaxation and entertainment.Many of the rentals come equipped with private pools, inviting hot tubs, and outdoor spaces great for enjoying the warm Florida weather. Expect amenities such as fully equipped kitchens, spacious living areas, and often outdoor seating areas or patios, which enhance the experience of outdoor living. Additionally, some properties may feature barbecue grills and lush gardens, providing a ideal setting for gatherings with family and friends.
Can I book pet-friendly holiday rentals in Uptown - Upper Duval?
In Uptown - Upper Duval, there are a variety of pet-friendly holiday rentals available, with around 14 options to choose from. This lively neighbourhood offers a mix of charming cottages and modern homes that often feature amenities such as private patios, fully equipped kitchens, and outdoor spaces, great for enjoying the pleasant Florida weather.Pet owners will appreciate the area's welcoming atmosphere, with easy access to pet-friendly parks and nearby beaches that allow for leisurely strolls with furry companions. The proximity to local shops and dining options enhances the experience, making it convenient for those looking to enjoy the vibrant community while travelling with pets.
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, Florida, where vibrant energy meets stunning coastal beauty. The peak season runs from January to March, drawing in a mix of sun-seekers and adventure enthusiasts eager to enjoy the lively option and outdoor activities that this charming area offers.During these months, visitors can bask in pleasantly warm temperatures, typically ranging from 20 to 27 degrees Celsius, making it ideal for exploring nearby beaches, indulging in watersports, or simply enjoying the local dining scene al fresco. The bustling streets come alive with events and festivals, providing ample opportunities for socialising and experiencing the local culture.If you're looking for a more budget-friendly option, consider visiting in October. While this month may be quieter, it offers a unique charm with fewer crowds, allowing for a more relaxed experience. Autumn in Uptown - Upper Duval is a great time to enjoy the local restaurants and shops at your own pace, with pleasant temperatures and a laid-back vibe.
Are there any remote work holiday rentals in Uptown - Upper Duval?
In Uptown - Upper Duval, Florida, there are numerous remote work holiday rentals available, with around 126 options to choose from. This vibrant area is known for its lively option and proximity to local attractions, making it an excellent choice for those looking to balance work and leisure. Many of these rentals come equipped with essential amenities for remote work, such as high-speed internet, dedicated workspaces with desk and chair, and complimentary Wi-Fi in the rooms.Additionally, guests can enjoy the convenience of well-furnished accommodations that often include full kitchens, comfortable living areas, and outdoor spaces for relaxation. The nearby attractions, including shops, restaurants, and cultural sites, provide ample opportunities to unwind after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are the top attractions in Uptown - Upper Duval, Florida, United States of America?
In Uptown - Upper Duval, Florida, visitors can enjoy a vibrant setting filled with attractions and local charm. The area is renowned for its lively nightlife, with numerous bars, restaurants, and shops lining the streets. The historic architecture adds character, making it a picturesque place to explore.One of the highlights is the famous Duval Street, where travellers can immerse themselves in the local culture, sampling fresh seafood and engaging in the vibrant arts scene. Nearby, the Key West Butterfly and Nature Conservatory offers a serene experience, showcasing beautiful butterflies in a lush setting.For those interested in history, the Ernest Hemingway Home and Museum is a must-visit, providing insights into the life of the famous author and the unique architecture of the property. Additionally, the Southernmost Point Buoy, a popular photo opportunity, is a short stroll away, marking the southernmost point in the continental United States.
Are all fees included in the Uptown - Upper Duval 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 Uptown - Upper Duval holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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 Uptown - Upper Duval holiday homes?
You can find great discounts on holiday homes in Uptown - Upper Duval 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 Uptown - Upper Duval holiday home booking on Stayz?
To find Uptown - Upper Duval 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 Uptown - Upper Duval?
A long-stay holiday home 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 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 Uptown - Upper Duval holiday home?
Book your Uptown - Upper Duval 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 Uptown - Upper Duval?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Uptown - Upper Duval 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.



