Owner Direct Vacation
Rentals in Uptown - Upper Duval
The Best Owner Direct Vacation Rentals in Uptown - Upper Duval. Explore thousands of vacation home rentals, large cabins, and villas near Uptown - Upper Duval
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Explore the Best Uptown - Upper Duval Vacation Homes
Looking for the perfect place to stay in Uptown - Upper Duval? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Uptown - Upper Duval character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
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Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Uptown - Upper Duval
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Popular Neighborhoods for Uptown - Upper Duval Vacation Rentals
What are the best areas to stay in Uptown - Upper Duval
Discover the top neighborhoods in Uptown - Upper Duval and choose a place that suits your stay.
Monday Apr 20
Uptown - Upper Duval, Key West
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Uptown - Upper Duval vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Uptown - Upper Duval
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How to Reserve Your Uptown - Upper Duval Vacation Rental
Booking Made Simple
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Uptown - Upper Duval Vacation Rental FAQs
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
There are 230 vacation rentals with private pools near Uptown - Upper Duval. Top-rated homes that have access to a swimming pool include:
- Private Heated Pool-2BR/2BA-OldTown for full Winter Jan 1 -March 31 -Weekly Maid
- Welcome to Parrot Dice! An Old Town tropical oasis with a private heated pool.
- Discover the lure of Casa Catalina, a blend of Key West charm and modern comfort
- *SWEPT AWAY @ OLD TOWN* Dreamy Private Home & Pool + LAST KEY SERVICES.
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:
Currently, the total number of properties listed in 2026 is over 1263 in the Uptown - Upper Duval area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Uptown - Upper Duval.