Best Vacation Homes in Uptown - Upper Duval
House
3 Bedrooms
3 Baths
5 Guests
Pet Friendly
Air Conditioner
Internet
Child Friendly
R3,465/Night
7 Nights - R24,250
House
10.0(4 Reviews)
1 Bedroom
1 Bath
3 Guests
398.26 ft²
- Pet Friendly
- Child Friendly
Security/Safety
R5,944/Night
7 Nights - R41,608
Cottage
10.0(6 Reviews)
1 Bedroom
1 Bath
Ocean View
Balcony/Terrace
View- Pet Friendly
R9,197/Night
7 Nights - R64,372
R14,915/Night
7 Nights - R104,397
House
10.0(3 Reviews)
1 Bedroom
1 Bath
2 Guests
Pool- View
Parking- Internet
R4,123/Night
7 Nights - R28,855
House
10.0(186 Reviews)
2 Bedrooms
2 Baths
6 Guests
765 ft²
Private Pool- Pool
- Balcony/Terrace
Kitchen
R11,436/Night
7 Nights - R80,049
House
10.0(137 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
Oceanfront
Fireplace/Heating- Pool
R12,749/Night
7 Nights - R89,242
Apartment
10.0(120 Reviews)
1 Bedroom
1 Bath
2 Guests
450 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R4,924/Night
7 Nights - R34,472
Uptown - Upper Duval Luxury Rentals
New
Hotel
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
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New
Hotel
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
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New
Hotel
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
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New
Hotel
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
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New
Hotel
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
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New
Hotel
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
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New
Hotel
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
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New
Hotel
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
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Uptown - Upper Duval Pet Friendly Vacation Rentals
Condo
10.0(74 Reviews)
1 Bedroom
1 Bath
4 Guests
731 ft²
- Pool
- Balcony/Terrace
- Pet Friendly
- Kitchen
R6,714/Night
7 Nights - R46,997
House
10.0(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
785.77 ft²
- Pet Friendly
- Child Friendly
- Security/Safety
R13,552/Night
7 Nights - R94,860
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
- Pool
- Balcony/Terrace
- Pet Friendly
- Parking
R15,421/Night
7 Nights - R107,940
Condo
10.0(66 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R7,291/Night
7 Nights - R51,031
House
10.0(2 Reviews)
1 Bedroom
1 Bath
8 Guests
882.64 ft²
- View
- Breakfast
- Pet Friendly
- Child Friendly
R8,736/Night
7 Nights - R61,155
House
10.0(38 Reviews)
3 Bedrooms
3 Baths
8 Guests
1370 ft²
- Oceanfront
Hot Tub- Ocean View
- Balcony/Terrace
R14,525/Night
7 Nights - R101,686
House
10.0(34 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Air Conditioner
R20,028/Night
7 Nights - R140,192
Apartment
10.0(27 Reviews)
1 Bedroom
1 Bath
2 Guests
475 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R2,268/Night
7 Nights - R15,873
Uptown - Upper Duval Large Vacation Homes
House
2 Bedrooms
5 Baths
14 Guests
2571 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
R40,009/Night
7 Nights - R280,056
Bed & Breakfast
9.3(1203 Reviews)
13 Bedrooms
13 Baths
40 Guests
317.95 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R6,053/Night
7 Nights - R42,376
House
10.0(150 Reviews)
5 Bedrooms
4 Baths
12 Guests
2700 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R32,563/Night
7 Nights - R227,932
Bed & Breakfast
9.3(30 Reviews)
7 Bedrooms
7 Baths
14 Guests
199.9 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R5,020/Night
7 Nights - R35,142
House
10.0(141 Reviews)
5 Bedrooms
5 Baths
12 Guests
2651 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
R28,931/Night
7 Nights - R202,522
House
10.0(101 Reviews)
6 Bedrooms
6 Baths
12 Guests
2644 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
R38,065/Night
7 Nights - R266,454
House
10.0(91 Reviews)
7 Bedrooms
7 Baths
16 Guests
2843 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R36,380/Night
7 Nights - R254,664
House
10.0(68 Reviews)
5 Bedrooms
4 Baths
10 Guests
4000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
R29,686/Night
7 Nights - R207,797
Why Choose Rent By Owner for your Uptown - Upper Duval Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Uptown - Upper Duval Vacation Rentals
Where are the best neighborhoods to stay in Uptown - Upper Duval?
Discover the charm of Uptown - Upper Duval in Key West, Florida, where vibrant local culture meets laid-back island living. Staying in this neighborhood places you close to the heart of Key West’s lively atmosphere while offering a tranquil retreat away from busier areas. Whether you're exploring nearby shops and eateries or enjoying the serene beaches, uptown offers the perfect balance for an authentic Florida Keys experience. Select from a variety of dependable vacation rentals that provide comfort and convenience during your stay in this inviting neighborhood within the beautiful surroundings of Key West.
Key West Historic District
In this vibrant district, you’re surrounded by the charming architecture and cultural richness that define the area’s unique character. Staying here offers convenient access to the region’s historic sites and lively local scene.
View 2294+ Rentals in Key West Historic DistrictOld Town
This neighborhood offers a central hub for exploring the region's renowned attractions and authentic local experiences. Your stay here puts you close to key amenities and the energetic atmosphere of this welcoming community.
View 2211+ Rentals in Old TownDowntown
Opting for accommodation in this area means immersing yourself in the dynamic core of the destination, with easy access to boutique shops, dining, and entertainment options that capture the essence of the region.
View 939+ Rentals in DowntownBest Times to Visit Uptown - Upper Duval
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, as the area's climate and seasonal events vary throughout the year, so planning your trip accordingly ensures you enjoy the beauty and vibrancy of this destination at its best.
Peak Season Highlights
Winter (December to April)
During this time, the area experiences its peak tourist season as visitors escape colder climates to enjoy the mild weather and sunny skies of this destination in Florida.
Average Temperature Daytime: 75°F to 80°F - Nighttime: 65°F to 70°F
Spring Break (March to April)
Spring break attracts many travelers seeking lively events and warm weather, making it one of the busiest times to visit here for those looking for vibrant local festivities.
Average Temperature Daytime: 78°F to 82°F - Nighttime: 67°F to 72°F
Off-Season Highlights
Summer (June to August)
The summer months see fewer visitors, offering a calmer experience with hot days perfect for relaxing by the water and exploring at your own pace.
Average Temperature Daytime: 85°F to 90°F - Nighttime: 75°F to 80°F
Fall (September to November)
Autumn brings cooler temperatures and fewer crowds, making it an ideal period to enjoy the scenic beauty and quiet streets of this region.
Average Temperature Daytime: 80°F to 85°F - Nighttime: 70°F to 75°F
Weekly Weather Forecast for Uptown - Upper Duval
How to Book Your Uptown - Upper Duval Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Uptown - Upper Duval
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy access to a private outdoor patio or balcony for relaxing in the sun.
- Take advantage of a lush, well-maintained garden area perfect for morning strolls or evening gatherings.
- Make use of a communal swimming pool to cool off during warm days in this tropical destination.
- Benefit from convenient outdoor grilling facilities to host your own barbecues.
- Relax in an inviting lounging area designed for outdoor comfort and leisure.
- Access shared or private parking spaces to easily explore the region's scenic spots.
- Utilize outdoor showers or wash stations, ideal after enjoying nearby beaches or water activities.
Top Attractions Around Uptown - Upper Duval
What attractions are nearby?
During your stay, you'll find a variety of nearby activities to enjoy, from exploring charming local shops to experiencing vibrant dining options, all conveniently close to this destination in the Uptown - Upper Duval area of Key West.
Family Activities
- Key West Eco Discovery Center: Engage your family with interactive exhibits and educational programs that highlight the region’s unique wildlife and ecosystems.
- Fort Zachary Taylor Historic State Park: Enjoy a day of swimming, picnicking, and exploring historic fortifications at this scenic spot near the area.
- Southernmost Point Buoy: Capture memorable family photos at this iconic landmark, a must-see in the region for visitors of all ages.
- Smathers Beach: Relax on the soft sands or try water sports like paddleboarding at this popular beach destination nearby here.
Adult Activities
- Historic Duval Street Tour: Explore the vibrant streets filled with colorful architecture, boutique shops, and lively cafes that capture the essence of this area's charm.
- Sunset Sail Adventure: Experience a tranquil sunset cruise along the coast, offering stunning views and a relaxing way to enjoy the region's natural beauty.
- Cuban Cuisine Tasting: Indulge in authentic flavors at local eateries known for their fresh seafood and traditional Caribbean dishes, perfect for food enthusiasts.
- Art and Cultural Gallery Visits: Discover local creativity by browsing through galleries showcasing regional art, capturing the spirit of the destination’s artistic community.
Other Places to Stay in Uptown - Upper Duval, FL
Simonton Beach
South Beach
Key West Butterfly and Nature Conservatory
City Zoo Gallery
Old Town
Uptown - Upper Duval Travel Tips
How Can You Make the Most of Your Stay?
- Explore local dining options: Take advantage of the area's renowned restaurants and cafes to enjoy authentic flavors unique to this vibrant destination.
- Plan outdoor activities: Make the most of the warm climate by scheduling water-based excursions or leisurely strolls through nearby parks and scenic spots.
- Utilize transportation options: Consider renting a bike or scooter to easily navigate the region and access its hidden gems without hassle.
- Book in advance: Secure your preferred vacation rentals early to ensure a comfortable stay in this popular area and enjoy all that it has to offer.
Transportation Options
- Key West Transit System: Offers convenient bus services that connect you to various points of interest within the area, making local travel straightforward and economical.
- Bike Rentals: An eco-friendly way to explore here at your own pace, with many rental shops offering bikes perfect for navigating the charming streets of this destination.
- Taxi Services: Available throughout the region, providing quick and reliable transportation options for getting around comfortably during your stay.
- Rental Cars: Easy to arrange from local providers, giving you the flexibility to explore beyond the immediate area at your convenience.
Local Customs Options
- Respect for Local Art and Architecture: You’ll find that appreciating the vibrant art scene and historic architecture is a key custom here, and supporting local artists and craftsmen adds to your authentic experience.
- Engaging with the Waterfront Community: Interacting with locals during waterfront gatherings or casual settings shows your respect for their maritime traditions and close-knit neighborhood vibe.
- Participating in Eco-Friendly Practices: Embracing sustainable habits, such as recycling and conserving water, aligns with the area's commitment to preserving its natural beauty for visitors and residents alike.
- Celebrating the Local Food Culture: Sampling fresh seafood and traditional dishes at local eateries allows you to immerse yourself in the region’s unique culinary customs and hospitality.
Frequently Asked Questions About Uptown - Upper Duval?
1. What are the top vacation rentals in Uptown - Upper Duval?
There are a lot of options in Uptown - Upper Duval. If you plan on staying in the Uptown - Upper Duval area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Uptown - Upper Duval:
- Almond Tree Inn Hotel - Adults Only
- ~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
- Hidden away near the Southernmost Point, Louisa's Hideaway is it!
- Everything Key West has to offer @ Mango Cottage
- NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking
- *CASA VICTORIA @ OLD TOWN* Historic 5BR Home & Pool + LAST KEY SERVICES.
- Key West Oasis, Seperate Cottage, Very Private Pool and Back Yard
- ~ GRAND MAISON ~ Spacious home on Duval St with pool and 4 ensuite bedrooms.
- Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
- Casa De Cuba A Beach House - Cuban Flair Steps From Duval
2. How many vacation rentals have private pools in Uptown - Upper Duval?
There are 248 vacation rentals with private pools near Uptown - Upper Duval. Top-rated RBO homes that have access to a swimming pool include:
- ~ INN COGNEATO ~Experience island life in a private oasis with heated pool.
- Luxurious Key West Pool Home block from Duval! Pool & Patio Recently Renovated!
- ~ COPA CABANA ~ Classic Key West cottage just a stone’s throw from the water.
- Private Heated Pool-2BR/2BA-OldTown for full Winter Jan 1 -March 31 -Weekly Maid
3. Which vacation homes in Uptown - Upper Duval are best for families?
If you are looking for a family-friendly vacation home in Uptown - Upper Duval, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Uptown - Upper Duval:
4. How many Rentbyowner vacation rentals are available in Uptown - Upper Duval?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1301 in the Uptown - Upper Duval area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Uptown - Upper Duval.
5. What is the cancellation policy for vacation rentals in Uptown - Upper Duval, Key West?
The cancellation policy varies depending on the specific property. You should review the listing details or contact the property owner directly to understand the terms regarding cancellations and refunds.
6. How do I secure my reservation at a vacation rental in this area?
Reservations are secured through the booking platform by following the property's booking process. Be sure to read the listing requirements and confirm your payment details to finalize your stay.
7. Are there any specific check-in and check-out times for vacation rentals here?
Check-in and check-out times are set by individual property owners. Please refer to the listing details or contact the host directly for accurate information about arrival and departure times.
8. Are there any additional fees or deposits required when booking a vacation rental in this destination?
Additional fees or deposits, such as cleaning fees or security deposits, are typically outlined in the listing. Contact the property owner if you need clarification on any extra charges.
9. What amenities are usually included with vacation rentals in this part of the city?
Amenities vary by property but often include essentials like Wi-Fi, kitchen facilities, and parking. For a detailed list, review the individual listing or speak directly with the host to ensure it meets your needs.
Uptown - Upper Duval Top Rated Vacation Rentals
Hotel
10.0(1003 Reviews)
1 Bath
- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
R5,075/Night
7 Nights - R35,534
Cottage
10.0(233 Reviews)
4 Bedrooms
2 Baths
7 Guests
1440 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
R15,048/Night
7 Nights - R105,327
House
10.0(202 Reviews)
3 Bedrooms
3 Baths
6 Guests
1154 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R17,618/Night
7 Nights - R123,323
House
10.0(133 Reviews)
4 Bedrooms
4 Baths
8 Guests
1800 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R27,066/Night
7 Nights - R189,459
House
10.0(111 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R27,189/Night
7 Nights - R190,324
House
10.0(88 Reviews)
3 Bedrooms
3 Baths
8 Guests
1541 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R16,150/Night
7 Nights - R113,051
House
10.0(80 Reviews)
4 Bedrooms
4 Baths
8 Guests
1456 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R18,040/Night
7 Nights - R126,279
House
10.0(77 Reviews)
3 Bedrooms
2 Baths
6 Guests
1201 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R16,226/Night
7 Nights - R113,574
