Uptown - Upper Duval vacation rentals

We found 452 vacation rentals — enter your dates for availability

Select from 190 houses, 33 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.
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Find out more about Uptown - Upper Duval

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 accommodation in Uptown - Upper Duval?
Houses are the most popular type of vacation rental in Uptown - Upper Duval, according to our data. Even if you’ve got a different idea about what you’d like, Vrbo has properties in many shapes and sizes. Explore our options to find your perfect fit.
How much does it cost to rent a vacation rental in Uptown - Upper Duval?
The average price for a vacation rental in Uptown - Upper Duval is based on a number of factors, such as property type, length of stay and season. Whether you’re searching for a sprawling villa with space for the whole family or a quaint cottage ideal for just you and the kids, just add your travel dates to discover stays with exceptional value.
How much does it cost to rent a beach house in Uptown - Upper Duval?
The average price for a vacation home near the beach in Uptown - Upper Duval will depend on when you’ll be there and the type and size of property you want. Find prices easily on Vrbo by entering your preferred travel dates and destination. Then use the filter tool to pick the number of bedrooms and amenities that you prefer, like WiFi, a pool and air conditioning.
Are there pet-friendly vacation rentals in Uptown - Upper Duval?
Yes. There are. You can choose from 276 vacation rentals that cater to pets in Uptown - Upper Duval. Lots of our pet-friendly vacation rentals have a garden for your furry friend to play in, complimentary treats, special dog beds and proximity to parks and green space. Apply the “Pets allowed” filter to find your pawfect vacation home on Vrbo.
Can I rent a house with a pool in Uptown - Upper Duval?
Tick the “pool” box in our handy filter tool and select from 222 houses with private pools in Uptown - Upper Duval on Vrbo. Lazy soak or races and ball games? Leisure activities are up to you when your Vrbo vacation property has its own swimming pool.
What are popular rental amenities in Uptown - Upper Duval?
A water view, a nearby waterfront and a beach view are rated the most popular rental amenities in Uptown - Upper Duval. Whether you’re taking a trip by yourself, with your sweetheart or as a family group, Vrbo will help you find a vacation home that matches your style with all the features you need.
Are there large group vacation rentals in Uptown - Upper Duval?
With 22 vacation rentals that can host 10 or more guests in Uptown - Upper Duval, there’s no need to leave anyone off your guest list. From fun family vacations to events like birthday parties and weddings, Vrbo will help you find a large group rental to suit the occasion.
Are there vacation rentals in Uptown - Upper Duval that welcome kids?
Bring the entire family together for a fun-filled adventure in Uptown - Upper Duval at one of our 276 family-friendly vacation homes. Lots of these stays feature conveniences that are great for getaways with the little ones, including laundries, extra bedrooms and outdoor spaces. Just check the “Properties good for families” filter and pick your favorite option.
What are the top attractions for families in Uptown - Upper Duval?
Keep the kids happy at these leading family-friendly attractions in Uptown - Upper Duval:

  • Smathers Beach
  • South Beach
  • Higgs Beach

Are there one-bedroom vacation rentals in Uptown - Upper Duval?
Yes, Uptown - Upper Duval has 109 one-bedroom rentals available. Usually situated in popular spots because of their smaller size, a one-bedroom rental is great if you’re getting away with your partner or a pal. And with home comforts like wireless internet and more privacy than a standard hotel, you’ll be able to chill out while exploring this amazing destination.
Can I find two-bedroom vacation rentals in Uptown - Upper Duval?
Uptown - Upper Duval has 78 two-bedroom vacation rentals to select from. Discover a vacation home with all the space and privacy you’re looking for at a price that’s hard to resist on Vrbo.
Are there vacation rentals with WiFi in Uptown - Upper Duval?
Whether you’d like to keep up with world events, make a video call or update your social media accounts, there are 47 vacation homes with WiFi in Uptown - Upper Duval. Check the “WiFi” box when searching on Vrbo and stay connected on your getaway.
How can I find vacation rentals with air conditioning in Uptown - Upper Duval?
Decide on your travel dates and then make use of the filters to view vacation rentals with air conditioning in Uptown - Upper Duval on Vrbo. With 274 air-conditioned properties to choose from here, you can look forward to a cool and comfy stay.
How old do you have to be to rent a vacation rental in Uptown - Upper Duval?
The minimum required age is generally 16, 18 or 21. It can change from property to property on Vrbo, so look at the rules of your chosen Uptown - Upper Duval vacation rental before making a booking.
How long can I rent a vacation rental in Uptown - Upper Duval for?
The amount of time you can book an Uptown - Upper Duval vacation rental for differs depending on the property. Simply enter your preferred travel dates to browse options that offer long-term stays. They have all the things you need to make your extended trip more convenient and enjoyable, such as kitchens and yards. Some vacation homes might also offer weekly or monthly discounted prices, so you can stay longer for less money.

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