Uptown - Upper Duval vacation rentals

We found 407 vacation rentals — enter your dates for availability

Select from 113 houses, 34 condos, and other vacation rentals to find the perfect place for your stay in Uptown - Upper Duval. Whether you’re staying in a vacation home with family or friends, you'll have the amenities you expect and more, which might include a hot tub and a washer and dryer. Whatever you're looking for, you'll be able to choose a rental for everyone's needs, including accessible or non-smoking choices.

Find spaces that suit your style

Find out more about Uptown - Upper Duval

Why visit Uptown - Upper Duval

  1. Charming Streets: Stroll along the picturesque Upper Duval Street, full of vibrant sights and sounds.
  2. Rich History: Discover historic houses and cultural landmarks that tell the story of Key West.
  3. Beautiful Beaches: Relax on stunning beaches, perfect for soaking up the sun and enjoying water activities.
  4. Diverse Accommodations: Choose from unique vacation rentals, including charming homes and modern condos.
  5. Family-Friendly Activities: Experience a variety of adventures suitable for all ages, ensuring fun for the whole family.

Popular types of accommodation around Uptown - Upper Duval

Looking for the perfect getaway in Uptown - Upper Duval? You're in the right place! Our top choices for vacation rentals include charming private homes, modern condos, and delightful cottages, all designed to enhance your stay. Whether you're seeking an Upper Duval vacation rental, a cozy Key West condo, or a unique experience in Old Key West, we offer a variety of options to suit your needs. Experience the vibrant charm of Uptown with confidence and ease!

  • Houses: The top choice for visitors in Uptown - Upper Duval, offering spacious and comfortable settings perfect for families and groups.
  • Condos: A popular option for those seeking modern amenities and a convenient location, ideal for couples or small families.
  • Cottages: These charming retreats provide a cozy atmosphere, perfect for a romantic getaway or a peaceful escape.
  • Apartments: A flexible accommodation choice, suitable for longer stays, with easy access to local attractions.
  • Caravan Parks: A unique option for those who enjoy a camping experience with added facilities and community atmosphere.**

Top attractions around Uptown - Upper Duval

Uptown - Upper Duval in Key West is perfect for family, business, and city-themed vacations. Visitors can explore a variety of attractions, including charming streets, beautiful beaches, and historic houses. This vibrant area offers a rich cultural experience for travellers, making it an ideal spot for those seeking a blend of relaxation and exploration. Enjoy the unique local atmosphere that Uptown - Upper Duval has to offer!

  1. Duval Street: A vibrant thoroughfare filled with lively bars, shops, and restaurants, perfect for experiencing the local nightlife and culture. Stroll along the street to enjoy street performers and the bustling atmosphere.
  2. Southernmost Point: A famous landmark marked by a buoy, celebrating its geographical significance. Capture memorable photos and soak in the beautiful ocean views while embracing the unique local culture.
  3. Ernest Hemingway Home and Museum: The historic residence of the renowned author, showcasing his life and work. Explore the lush gardens and learn about Hemingway's fascinating history in Key West.

Things to do recommended for families

Families visiting Uptown - Upper Duval in Key West can enjoy a refreshing day at the MLK Community Pool & Community Center, located 322m away. This pool offers a fun atmosphere with family-friendly vibes, perfect for swimming and outdoor activities.

Things to do recommended for groups

In Uptown - Upper Duval, your group can enjoy a round of golf at the Key West Golf Club, explore unique finds at The Kite House, or experience the vibrant performances at the Key West Burlesque Theater, all while soaking up the local culture and outdoor charm.

What do I need to keep in mind when booking a vacation around Uptown - Upper Duval

When planning your trip, whether you're travelling with a group, enjoying time with family, bringing along your pets, or seeking extended stays, be sure to filter your options based on what matters most to you. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Uptown - Upper Duval with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group get-togethers. Thankfully, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Uptown - Upper Duval with young kids: Travelling with young children can present its challenges. 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 family-friendly attractions.
  • Taking your pets with you to Uptown - Upper Duval: For many families, a vacation wouldn’t be the same without their beloved pets. If this resonates with you, explore Vrbo properties that welcome furry companions. Many pet-friendly accommodations offer feeding bowls and comfy beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Uptown - Upper Duval: If you're searching for vacation rentals that offer 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 rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay around Uptown - Upper Duval

Uptown - Upper Duval in Key West offers an unforgettable blend of tropical charm and vibrant city life. Explore the lively Upper Duval Street, where beautiful sights and sounds await at every corner. The uptown neighbourhood boasts rich historical experiences, perfect for families seeking adventure. Whether you're strolling along Duval Street or discovering hidden gems nearby, this area is sure to provide a memorable vacation filled with excitement and relaxation.

  • Old Town Key West: Old Town Key West is a vibrant neighborhood located a mere 322m from Uptown - Upper Duval. This historic area is known for its charming streets lined with colourful conch houses and offers a delightful mix of city, family, and business experiences. Visitors can explore a variety of shopping areas and enjoy leisure activities at nearby resorts. Notable attractions include local beaches that provide perfect spots for family fun and relaxation, making it an ideal destination for tourists seeking both culture and leisure.
  • Key West Historic District: Situated 644m from Uptown - Upper Duval, the Key West Historic District is a must-visit for anyone interested in the rich history of the island. This area attracts travellers looking for a blend of city, family, and business experiences. With easy access to shopping areas and resorts, visitors can immerse themselves in the local culture. The proximity to beautiful streets and family-friendly beaches enhances the experience, providing plenty of opportunities for exploration and enjoyment.
  • Downtown Key West: Just 322m from Uptown - Upper Duval, Downtown Key West is the bustling heart of the island, offering an exciting mix of city vibrancy, family-friendly activities, and business opportunities. Visitors can enjoy a wide range of shopping areas and resorts, making it a convenient hub for tourists. The local landmarks, including picturesque streets and inviting beaches, make Downtown Key West a fantastic spot for those looking to soak up the sun and engage in the lively atmosphere of this beautiful destination.

Best time to go to Uptown - Upper Duval

If you're planning a trip to Uptown - Upper Duval, 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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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

Looking to save on your next adventure? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to refine your search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform where you can easily plan new trips, resume from where you last stopped, or review and arrange your travel plans. You can view your saved or booked properties neatly organized under Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please 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 Uptown - Upper Duval?
In Uptown - Upper Duval, condos are the most popular type of vacation rental, with around 26 available in the area. These condos are typically located near vibrant points of interest, such as local restaurants and shops, making them an ideal choice for those wishing to explore the lively atmosphere. Most condos come equipped with modern amenities, including fully fitted kitchens, spacious living areas, and often private balconies where guests can enjoy the warm Florida weather.
Are there any beach house rentals in Uptown - Upper Duval?
In Uptown - Upper Duval, Florida, there are approximately 46 beach house rentals available. This vibrant neighbourhood is known for its lively atmosphere and proximity to various attractions, including the famous Duval Street and the beautiful beaches of Key West. The beach houses typically feature amenities such as spacious living areas, fully equipped kitchens, and outdoor decks or patios ideal for enjoying the warm Florida weather. Many properties also offer private pools and easy access to local dining and entertainment options, making them superb for families or groups seeking a lively beach getaway.
How much does it cost to rent a vacation home in Uptown - Upper Duval?
Prices for vacation 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 travelling 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.
Are there any discounts for Uptown - Upper Duval vacation 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 vacation rental amenities include heated pools, fully equipped kitchens, and outdoor patios. Many properties offer shared pools, ideal for socialising with other guests, while private decks or patios allow for a relaxing space to enjoy the warm Florida weather.
Are there any family house rentals in Uptown - Upper Duval?
In Uptown - Upper Duval, Florida, there are numerous family-friendly house rentals available, with around 25 options to choose from. This vibrant area is ideal for families, offering spacious homes that often come equipped with multiple bedrooms, full kitchens, and inviting outdoor spaces superb for relaxation and play. Many properties feature amenities such as private pools, barbecues, and comfortable living rooms, ensuring a pleasant stay for everyone.
Can I rent a vacation home with a pool or hot tub in Uptown - Upper Duval?
In Uptown - Upper Duval, Florida, there are plenty of vacation homes available for rent that feature both pools and hot tubs, with approximately 32 options for homes with pools and 23 with hot tubs. This vibrant neighbourhood is known for its lively atmosphere, offering easy access to local attractions, dining, and nightlife.
Are there any Uptown - Upper Duval vacation rentals with parking?
Vrbo offers a wide selection of vacation 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 vacation rentals in Uptown - Upper Duval?
In Uptown - Upper Duval, there are several pet-friendly vacation rentals available, making it a great choice for travellers wishing to bring their furry companions along. This vibrant area is known for its lively atmosphere, with numerous shops, restaurants, and entertainment options within easy reach. Many vacation rentals here come equipped with modern amenities such as fully stocked kitchens, outdoor spaces, and comfortable living areas, ensuring a pleasant stay for both humans and pets.
Can I find long-stay vacation rentals in Uptown - Upper Duval?
A long-stay vacation 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 vacation rental?
March is the most popular time to visit Uptown - Upper Duval, when vibrant energy fills the air during the peak season from January to March. This period attracts a diverse mix of travellers looking to enjoy the warm weather, with temperatures typically in the low 20s Celsius, great for outdoor activities and exploration. Visitors can take leisurely strolls through the lively streets, soak in the local culture, and indulge in the delightful culinary scene that Upper Duval has to offer.

The peak season is characterised by bustling tourist activity, with many events and festivities taking place, making it ideal for those seeking a lively atmosphere. You'll find plenty of opportunities for sightseeing, whether it's visiting charming shops or enjoying the stunning sunsets by the waterfront.

If you're looking for a more budget-friendly experience, consider planning your visit in October. This month provides a quieter atmosphere, allowing you to explore the area at a relaxed pace while still enjoying pleasant weather. It's a great time to appreciate the natural beauty of the region without the summer crowds.
Are there any remote work vacation rentals in Uptown - Upper Duval?
In Uptown - Upper Duval, there are numerous remote work vacation rentals available, with around 48 options to choose from. This vibrant area of Key West is known for its lively atmosphere, energetic shops, and proximity to beautiful beaches and parks. Many of the rentals cater specifically to remote workers, offering amenities such as high-speed Wi-Fi, dedicated office spaces with desks and chairs, and comfortable living areas conducive to productivity. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Uptown - Upper Duval vacation rental?
Book your Uptown - Upper Duval 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 Uptown - Upper Duval?
In Uptown - Upper Duval, visitors can enjoy a vibrant atmosphere filled with lively shops, restaurants, and art galleries. This area is renowned for its lively nightlife, with numerous bars offering live music and entertainment. The nearby Key West Butterfly and Nature Conservatory is a must-see for those interested in nature and wildlife, while the Ernest Hemingway Home and Museum provides a glimpse into the life of the famous author. Vacation rentals in this neighbourhood often feature charming architecture and easy access to nearby beaches, making it a great base for exploring the local attractions.
Can I change or cancel my Uptown - Upper Duval home rental booking on Vrbo?
To find Uptown - Upper Duval 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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Uptown - Upper Duval 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

More Vacation Ideas