Uptown - Upper Duval vacation rentals
We found 408 vacation rentals — enter your dates for availability
Select from 113 houses, 34 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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SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
Sleeps 8 · 3 bedrooms · 3 bathrooms
9.8 out of 10
exceptional
(197 reviews)
Top rated rentals - Uptown - Upper Duval

Quiet Stay in Great Location for Two Couples
10 out of 10
exceptional
(19 reviews)
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
We have stayed at many different properties in Key West and this one was the best for two couples. The location at the end of a quiet dead end street was exactly what we were looking for, no road noise. The bedrooms were spacious and fairly equal for two couples. The outdoor porches and community pool and gardens were enjoyable as well.
Tim K.
Stayed Nov 2025
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value
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