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 kitchens. Prices start at $133 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 1,074 vacation rentals around Old Town. From 512 house rentals to 309 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: 794 vacation rentals
  • Uptown/Upper Duval: 267 vacation rentals
  • Meadows: 571 vacation rentals
  • Midtown: 1,210 vacation rentals
  • New Town: 379 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:

  • Higgs Beach: 1,495 vacation rentals
  • Florida Keys Eco - Discovery Center: 1,489 vacation rentals
  • Custom House Museum: 1,490 vacation rentals
  • Key West Wildlife Center: 1,495 vacation rentals
  • Southernmost Point: 1,489 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 512 Houses in Old Town. Our other popular types of vacation rentals in Old Town include:

  • Condos/Apartments: 309 rentals available
  • Cottages: 93 rentals available
  • Bungalows: 93 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 860 vacation rentals with pool available in Old Town. Please use our search bar to access the selection of vacation rentals available.