Uptown - Upper Duval holiday homes
We found 408 holiday rentals — enter your dates for availability
Select from 161 houses, 34 flats and other holiday rentals to find the perfect place for your stay in Uptown - Upper Duval. 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
Map Attractions
Key West Butterfly and Nature Conservatory
Find the best place to stay - Uptown - Upper Duval

Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking
Sleeps 12 · 4 bedrooms · 2 bathrooms
9.2 out of 10
wonderful
(5 reviews)

ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.8 out of 10
exceptional
(136 reviews)

LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!
Sleeps 8 · 3 bedrooms · 2+ bathrooms
9.8 out of 10
exceptional
(221 reviews)

Duval Delight | Recently Remodeled Condo on Duval!
Sleeps 8 · 1 bedroom · 1+ bathroom
9.8 out of 10
exceptional
(23 reviews)
- 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