Downtown Key West vacation rentals
We found 856 vacation rentals — enter your dates for availability
Find the perfect place for your stay in Downtown Key West by choosing from 76 houses, 59 apartments, and other vacation rentals. Whether you're traveling with family, friends, or just your furry companion, vacation homes have the amenities you expect for your stay, such as air conditioning and WiFi. No matter what you're looking for, you'll find a rental for everyone's needs, including a place that is accessible or non-smoking.
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find properties near top attractions in Downtown Key West
Map Attractions
1
Ernest Hemingway Home and Museum
2
San Carlos Institute - Casa Cuba
Find the best place to stay - Downtown Key West
Showing deals for: Oct 8 - Oct 11
Heavenly Hideout at Rainbows End Key West - Steps from Duval w Private Pool
Sleeps 8 · 4 bedrooms · 4 bathrooms
9.69.6 out of 10
Exceptionalexceptional
45 reviews(45 reviews)
The current price is $1,096
$1,096
All fees included
Key West Wabi Sabi - Authentic Downtown Cottage w Pool - Steps Off Duval
Sleeps 8 · 4 bedrooms · 3+ bathrooms
9.29.2 out of 10
Wonderfulwonderful
43 reviews(43 reviews)
The current price is $1,047
$1,047
All fees included
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
Sleeps 4 · 1 bedroom · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
237 reviews(237 reviews)
The current price is $383
$383
All fees included
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
Sleeps 10 · 5 bedrooms · 3+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
102 reviews(102 reviews)
The current price is $1,685
$1,685
All fees included
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
Sleeps 8 · 3 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
184 reviews(184 reviews)
The current price is $913
$913
All fees included
Nassau suite-2 bedroom 2 bath, a block off Duval St w/pool, parking
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
109 reviews(109 reviews)
The current price is $554
$554
All fees included
Top rated rentals - Downtown Key West
Awesome place
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
A great price and the best location had a great stay and will be definitely be booking again ! Management and maintenance were very accommodating and friendly.. So glad to have found this place convenient,clean and great price .
chad b.
Stayed Jun 2025
The perfect spot
1010 out of 10
Exceptionalexceptional
10 reviews(10 reviews)
Stayed with my girlfriend and we enjoyed our stay very much. The location is absolutely perfect, right off of Duval street but away enough from the noise. It was very clean and cute inside, has all the amenities you could need. I highly recommend this place!
Conner S.
Stayed Jun 2025
Honeymoon
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Beautiful and cozy little place! Perfect location!
Justin E.
Stayed May 2025
Jasmine House
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
What a wonderful find! We couldn't ask for anything more in a rental home in Paradise! Property manager, Tracie, was amazingly helpful, kind, and went out of her way to make sure all went well! We can't wait to come back in 2026!
Terri G.
Stayed Mar 2025
Amazing owner and management. Very responsive and courteous!
1010 out of 10
Exceptionalexceptional
1 review(1 review)
We enjoyed 2 months at the Shipwreck Suite during peak winter season in KW. The location is absolutely amazing! When we had some issues with climate control during the really hot days the owner bent over backwards to make sure we and our puppies stayed cool and comfortable. Highly recommend this spot especially for big weekends on Duval with parades or fantasy fest.
Jay H.
Stayed Mar 2025
Dancing Rooster stay: Family - 3 couples
1010 out of 10
Exceptionalexceptional
122 reviews(122 reviews)
The property was clean and functional. It was conveniently located just 1 block from Duval. 6 of us stayed 4 nights. Kitchen was small but worked for us. We had breakfast and lunches, plus 1 family dinner where we used the BBQ grill. Very satisfied and would stay again. it wasn't problem for us but you had to go through bedroom2 to get to bedroom 3 from the interior. Bedroom 3 also had its own exterior door to allow you to exit and re-enter via main door to avoid passing through BR#2.
Brett M.
Stayed Jan 2025
Perfect location, exceptional deal
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Location 1 block off duval, right about the middle point between the ocean and the Gulf. And i didn't have to break the bank to stay. Would definitely recommend.
David P.
Stayed Apr 2024
Quiet Location
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Everything was super easy from the check in to check out. The location is a block from all the action on Duval but absolutely no noise when at home. Parking & the bicycles were a huge plus. All the appliances and interior are ultra modern. We will be back. Ed K
Ed K.
Stayed Feb 2024
Find out more about Downtown Key West
Frequently asked questions
What is the most popular type of vacation rental accommodation in Downtown Key West?
Based on our data, apartments are the most sought-after property type in Downtown Key West. But that goes without saying, everyone's idea of the perfect trip is bound to be different. Vrbo has vacation homes in a variety of shapes and sizes, and we'll help you to find your ideal match.
How much does it cost to rent a vacation rental in Downtown Key West?
Season, property type and length of stay are some of the conditions that can influence the price of a vacation home. Simply click on your dates of travel to find your perfect escape. From homey country cottages to sprawling luxury villas, all Vrbo vacation rentals offer unbeatable value.
How much does it cost to rent a beach house in Downtown Key West?
Prices for beach houses in Downtown Key West can vary depending on the type and size of the property and when you plan to travel. Simply enter your dates of travel into Vrbo and how many guests to see your options and prices. From there you can use our filter tool to narrow down your search by nearby activities, amenities, ratings and more.
Are there pet-friendly vacation rentals in Downtown Key West?
With 162 properties that host four-legged guests, your furry little friend can join you on your Downtown Key West break. Use the filter tool to browse our pet-friendly vacation rentals and find a stay that'll set tails wagging on Vrbo.
Can I rent a house with a pool in Downtown Key West?
Add another level of fun to your trip by booking your crew into one of the 109 houses with a private pool in Downtown Key West. Use our handy search filter to find the kind of property you want on Vrbo, and then spend leisurely days splashing about in a swimming pool that's for your use only.
What are popular rental amenities in Downtown Key West?
Some of the most popular rental amenities guests are looking for in Downtown Key West include a swimming pool, an electric car charging station and a beach view. Whether you're hitting the road with your besties, family or even pets, Vrbo vacation homes feature the best amenities for making epic memories with the people you love.
Are there large group vacation rentals in Downtown Key West?
With 26 vacation rentals that can host 10 guests or more in Downtown Key West, there's no need to leave anyone off your guest list. From fun family vacations to events like Christmas or New Year's Eve parties, Vrbo will help you find a large group rental to suit the occasion.
Are there vacation rentals in Downtown Key West that welcome kids?
Bring the entire group together for the adventure of a lifetime in Downtown Key West at one of our 161 family-friendly vacation properties. Lots of these stays feature conveniences that are suitable for trips with the kids, such as kitchens, living rooms and entertainment areas. Simply click on the "Properties good for families" filter and book your favorite.
Are there one-bedroom vacation rentals in Downtown Key West?
You can choose from 52 one-bedroom rentals in Downtown Key West. Whether you want a secluded cottage or an upmarket condo, our one-bedroom properties are great if you don't need lots of room. One of the best parts about having your own digs? You won't need to share your vacation with strangers.
Can I find two-bedroom vacation rentals in Downtown Key West?
Gather your nearest and dearest and relax in total privacy and comfort in one of the 45 two-bedroom vacation homes Downtown Key West has to offer.
Are there vacation rentals with WiFi in Downtown Key West?
You can choose from 64 vacation rentals with WiFi in Downtown Key West. If you'd like to disconnect from daily life on your break, but still need to be connected to the web, these properties are just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Downtown Key West?
Downtown Key West has 161 vacation rentals where you can unwind in air-conditioned comfort. To locate a property on Vrbo that provides this amenity, choose your travel dates and use the handy filter tool to select the "air conditioning" box.
How old do you have to be to rent a vacation rental in Downtown Key West?
The minimum age requirements can vary across properties on Vrbo, so check the rules of the vacation rental in Downtown Key West you're interested in. But normally, it's 16, 18 or 21.
How long can I rent a vacation rental in Downtown Key West for?
The amount of time you can book a Downtown Key West vacation home for is down to the property. Just put in your preferred travel dates to browse available options that offer long-term stays. They include everything you need to make your extended getaway more comfortable such as kitchens and laundries. Some Vrbo vacation properties may also offer discounted weekly or monthly prices, so you can hang around longer for less.
Does Vrbo offer discounts for vacation homes in Downtown Key West?
Whether you're eyeing off one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you're sure to score some fabulous deals and discounts on Vrbo. From short stays to extended getaways, we've got the ideal place for your next Downtown Key West escape.