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

Discover a selection of 1,500 vacation rentals in Old Town Key West, 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 $98 per night, and houses and cottages are popular options for a stay in Old Town Key West. Either way, you'll find a rental for everyone's needs.

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Find the best place to stay — Old Town Key West

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Stayed Jun 2022

Our stay at the Heron

Easy booking, easy check in, lovely to have the store on the corner and a bar/liquor store directly across the street. Bummed about the beaches with in walking distance, bad time of year with the sea grass and smell. Great beach a little over a mile ...

Stayed May 2022

Graduation gift

My girlfriend just graduated from Rn school and a trip.to key west was her gift. It was her first time down there. The house was perfect. Walking range to all the hot spots, the beach and was great for the morning coffee. She loved the big shower and...

Stayed May 2022

Great place

Gardenia Getaway was a great place - very close to everything yet the street was very quiet. Be aware to bring plastic forks, etc with you - there are none there. Just a couple mugs & a few glasses. No plates or anything else. Otherwise this was ...

Stayed May 2022

Nice property

House and deck need a little attention but it is a nice location. Place is small but just right for the 2 of us. Be aware- if someone is using the loft room and you have any mobility issues. Loved the little pool and that grocery is across the street...

Stayed May 2022

Excellent location,very quiet!

We were very happy with our stay. The proximity to Duval Street and to the shipyard annex swimming pool was a great attribute to this location. The unit was very clean , and roomy enough for four adults to share. We are looking forward to our next tr...

Stayed May 2022

Tony’s Birthday week

We loved staying in your cottage Pam!!! So clean and had everything we could of ever asked for. Your dining suggestions were so helpful. We lover the le Creperie restaurant. We also loved Baggatele, and La Gragnite. Marquisa was good as well. We went...

Stayed May 2022

Beautiful!

Wonderful little efficiency apartment. Very clean and nice pool. We also had a ga grill for ur use. Private patio, which was nice for early morning coffee. Close to Duval. We will definitely be back.<br /> Someone local checked to see if we were enj...

Stayed May 2022

35th anniversary, our Coral, so snorkeling trip

The location of the Truman Annex is perfect. Maybe using VRBO only for advertising purposes is the way of Florida, but I wish we had gone directly through the real estate office and saved 10%. Paying 10% on the tax is obnoxious because the VRBO fee s...

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

Our 2022 property listings offer a large selection of 1,467 vacation rentals around Old Town Key West. From 663 house rentals to 66 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Old Town Key West?

Yes, of course. Vrbo has 663 Houses in Old Town Key West. Our other popular types of vacation rentals in Old Town Key West include:

Cottages: 66 rentals available
Condos/Apartments: 525 rentals available
Bungalows: 66 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 Key West?

Yes, you can select your preferred vacation rental with pool among our 1,182 vacation rentals with pool available in Old Town Key West. Please use our search bar to access the selection of vacation rentals available.