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 air conditioning. Prices start at $145 per night, and houses and condos are popular options for a stay in Old Town. Either way, you'll find a rental for everyone's needs.
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How many vacation rentals are available around Old Town, Key West?

Our 2020 property listings offer a large selection of 1,076 vacation rentals around Old Town. From 501 house rentals to 310 condo and apartment 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: 791 vacation rentals
  • Uptown - Upper Duval: 254 vacation rentals
  • Meadows: 575 vacation rentals
  • New Town: 397 vacation rentals
  • Truman Annex: 833 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: 1,513 vacation rentals
  • Custom House Museum: 1,514 vacation rentals
  • Key West Wildlife Center: 1,520 vacation rentals
  • Southernmost Point: 1,513 vacation rentals
  • Key West Harbour: 1,718 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 501 Houses in Old Town. Our other popular types of vacation rentals in Old Town include:

  • Condos/Apartments: 310 rentals available
  • Cottages: 94 rentals available
  • Bungalows: 94 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 863 vacation rentals with pool available in Old Town. Please use our search bar to access the selection of vacation rentals available.

    Explore destinations around Old Town

    Florida Keys Eco - Discovery Center
    1,513 vacation rentals
    Custom House Museum
    1,514 vacation rentals
    Key West Wildlife Center
    1,520 vacation rentals
    Southernmost Point
    1,513 vacation rentals
    Key West Harbour
    1,718 vacation rentals
    South Beach
    1,514 vacation rentals
    Florida Keys National Marine Sanctuary
    1,513 vacation rentals
    Fort Zachary Taylor Historic State Park
    1,512 vacation rentals
    Schooner Western Union
    1,514 vacation rentals
    Mallory Square
    1,514 vacation rentals
    Harry S. Truman Little White House
    1,514 vacation rentals
    Fort East Martello Museum and Gallery
    1,674 vacation rentals
    Ernest Hemingway Home and Museum
    1,514 vacation rentals
    The Oldest House - Key West
    1,514 vacation rentals
    Audubon House and Tropical Gardens
    1,514 vacation rentals
    Key West Lighthouse and Keeper's Quarters Museum
    1,514 vacation rentals
    Nancy Forrester's Secret Garden
    1,514 vacation rentals
    Red Barn Theater
    1,514 vacation rentals
    Key West Butterfly and Nature Conservatory
    1,514 vacation rentals
    Robbie's
    1,682 vacation rentals