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 $101 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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Top rated rentals — Old Town
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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 683 house rentals to 91 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: 1,536 vacation rentals
  • Custom House Museum: 1,540 vacation rentals
  • Key West Wildlife Center: 1,545 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 683 Houses in Old Town. Our other popular types of vacation rentals in Old Town include:

  • Cottages: 91 rentals available
  • Condos/Apartments: 312 rentals available
  • Bungalows: 91 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 878 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
    1,536 vacation rentals
    Custom House Museum
    1,540 vacation rentals
    Key West Wildlife Center
    1,545 vacation rentals
    Southernmost Point
    1,539 vacation rentals
    Key West Harbour
    1,749 vacation rentals
    Florida Keys National Marine Sanctuary
    1,539 vacation rentals
    Fort Zachary Taylor Historic State Park
    1,538 vacation rentals
    Schooner Western Union
    1,540 vacation rentals
    Mallory Square
    1,540 vacation rentals
    Harry S. Truman Little White House
    1,540 vacation rentals
    Fort East Martello Museum and Gallery
    1,706 vacation rentals
    Ernest Hemingway Home and Museum
    1,539 vacation rentals
    The Oldest House - Key West
    1,540 vacation rentals
    Audubon House and Tropical Gardens
    1,540 vacation rentals
    Key West Lighthouse and Keeper's Quarters Museum
    1,540 vacation rentals
    Nancy Forrester's Secret Garden
    1,540 vacation rentals
    Red Barn Theater
    1,540 vacation rentals
    Key West Butterfly and Nature Conservatory
    1,540 vacation rentals
    Robbie's
    1,714 vacation rentals
    Donkey Milk House
    1,540 vacation rentals