Old Town, Key West Vacation Rentals: house rentals & more

Discover a selection of 1,000 vacation rentals in Old Town, Key West that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $102 per night, and houses and cottages are popular options for a stay in Old Town. Either way, you'll find a rental for everyone's needs.

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Find the best place to stay — Old Town

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Search 1,088 vacation rentals

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How many vacation rentals are available around Old Town, Key West?

Our 2020 property listings offer a large selection of 1,088 vacation rentals around Old Town. From 685 house rentals to 92 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to Old Town?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Old Town:

Historic Seaport: 802 vacation rentals
Uptown - Upper Duval: 266 vacation rentals
Meadows: 590 vacation rentals
New Town: 390 vacation rentals
Truman Annex: 850 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Old Town?

Vrbo offers a large selection of vacation rentals near lovely places in Old Town. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

Florida Keys Eco - Discovery Center: 1,539 vacation rentals
Custom House Museum: 1,540 vacation rentals
Key West Wildlife Center: 1,541 vacation rentals
Southernmost Point: 1,539 vacation rentals
Key West Harbour: 1,749 vacation rentals

But there are many other points of interest around Old Town listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Old Town?

Yes, of course. Vrbo has 685 Houses in Old Town. Our other popular types of vacation rentals in Old Town include:

Cottages: 92 rentals available
Condos/Apartments: 311 rentals available
Bungalows: 92 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Townhouses and more.

Can I find a vacation rental with pool in Old Town?

Yes, you can select your preferred vacation rental with pool among our 876 vacation rentals with pool available in Old Town. Please use our search bar to access the selection of vacation rentals available.