Downtown Key West holiday lettings

We found 855 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Downtown Key West by choosing from 76 houses, 59 apartments and other holiday rentals. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the best amenities for spending time at your holiday home, including parking and a TV. Whatever you're looking for, you'll find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday rental accommodation in Downtown Key West?
Houses are the most popular type of holiday rental in Downtown Key West, according to our data. Even if you have something different in mind, Vrbo has holiday homes in many sizes and shapes. Look through our options to find your perfect pad.
How much does it cost to rent a holiday rental in Downtown Key West?
The average price for a holiday home in Downtown Key West is based on a number of factors, like property type, length of stay and season. Whether you're dreaming about a sprawling villa with lots of bedrooms or a comfy cabin just enough for two, just enter your travel dates to see stays with terrific value.
How much does it cost to rent a beach house in Downtown Key West?
Prices for beach houses in Downtown Key West will vary depending on the size and type of the property and time of year you're travelling. Just enter your travel dates 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 ratings, nearby activities and more.
Are there pet-friendly holiday rentals in Downtown Key West?
Good news. There are. Take your pick of 146 holiday rentals that welcome pets in Downtown Key West on Vrbo. Our furry companions also deserve a getaway, so simply use our search function for pet-friendly holiday rentals to find a pad where your pup can join in the fun.
Can I rent a house with a pool in Downtown Key West?
Add a whole other level of fun to your adventure by booking your crew into one of the 94 houses with a private pool in Downtown Key West. Use our search filter to find the kind of property you want on Vrbo, and then spend your downtime splishing and splashing in a swimming pool that's exclusively for you.
What are popular rental amenities in Downtown Key West?
When it comes to rental amenities that guests look for in Downtown Key West, an electric car charging station, a garden and a fireplace are the most popular. With Vrbo holiday homes, there are choices to fit your taste and style, whether you're going on a trip with your partner, family members or even pets.
Are there large group holiday rentals in Downtown Key West?
With 19 holiday rentals that can host 10 guests or more in Downtown Key West, you don't have to hold back on your invites. From family holidays to events like birthday parties and weddings, Vrbo can help you find a large group rental to suit the occasion.
Are there holiday rentals in Downtown Key West that welcome kids?
Downtown Key West has 146 family-friendly holiday rentals. And booking a stay that welcomes youngsters is simple with our "Properties good for families" filter. On top of having the whole place to yourselves, you'll have access to amenities and perks like extra bedrooms, yards and private pools.
What are the top attractions for families in Downtown Key West?
Keeping the kids happy during your stay in Downtown Key West is a cinch with these leading family-friendly attractions:

  • Smathers Beach
  • South Beach
  • Higgs Beach

Are there one-bedroom holiday rentals in Downtown Key West?
Downtown Key West has 47 one-bedroom rentals on offer. Typically situated in well-regarded areas due to their compact size, a one-bedroom rental is great if you're travelling with a pal or your partner. And with comforts like laundry facilities and more privacy than a standard hotel, you'll be able to kick back and relax while exploring this top destination.
Can I find two-bedroom holiday rentals in Downtown Key West?
Downtown Key West has 42 two-bedroom holiday rentals for you to pick from. Experience a holiday home with all the privacy and space you want at a price that won't break the bank on Vrbo.
Are there holiday rentals with WiFi in Downtown Key West?
Take your pick of 43 holiday rentals with WiFi in Downtown Key West. If you'd like to disconnect from daily life during your escape, but still need to be connected to the internet, these properties are for you. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Downtown Key West?
Downtown Key West has 145 holiday rentals where you'll be able to relax in air-conditioned comfort. To find a stay on Vrbo that features 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 holiday rental in Downtown Key West?
The minimum age requirements can differ across properties on Vrbo, so look at the rules of the holiday rental in Downtown Key West you want to book. But typically, it's 16, 18 or 21.
How long can I rent a holiday rental in Downtown Key West for?
The amount of time you can stay in a Downtown Key West holiday rental for is up to the property. Just put in your dates of travel to see options offering longer term stays. They come with the things you need to make your extended getaway more enjoyable like air conditioning and kitchens. Some holiday homes may also offer weekly or monthly discounted prices, so you can stay longer for less money.

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