Uptown - Upper Duval holiday homes
We found 406 holiday rentals — enter your dates for availability
Select from 160 houses, 33 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.
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
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

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

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

SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
Sleeps 8 · 3 bedrooms · 3 bathrooms
9.8 out of 10
exceptional
(185 reviews)

Yellowfin Ledge | Inviting Getaway On Duval! Balcony!
Sleeps 3 · 1 bedroom · 1 bathroom
9.4 out of 10
exceptional
(18 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