Old Town Key West holiday rentals
We found 1,612 holiday rentals — enter your dates for availability
Select from 725 houses, 278 flats and other holiday rentals to find the perfect place for your stay in Old Town Key West. Whether you’re staying in a holiday home with family or friends, you'll have the amenities that you expect and more, such as parking and air conditioning. Whatever you're looking for, you're sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Old Town Key West
Showing deals for:10 Oct - 17 Oct
Image gallery for Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St

9.4 out of 10 rating
Exceptional
(47 reviews)
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
Key West, FL
7% off
Price is S$5,317
S$760 per night
includes taxes & fees
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Find the best place to stay - Old Town Key West

CORNISH SUITE @ Inn on Fleming ~ ADULTS ONLY 3rd Floor 2 BR w/Shared Pool!
Sleeps 4 · 2 bedrooms · 1 bathroom
9.0 out of 10
wonderful
(18 reviews)
Top rated rentals - Old Town Key West

AMAZING PROPERTY - BEST LOCATION
10 out of 10
exceptional
(145 reviews)
This is the third stay in this property in three years! It fits our needs PERFECTLY!! The owner and property manager take great care of the property and immediately deal with issues (issues are extremely rare)!
We will continue to enjoy this property for years to come!
Tim G.
Stayed Sept 2022
- 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