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 $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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Find the best place to stay — Old Town

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Search 1,088 vacation rentals

Stayed Nov 2020

First Time in Key West

Checking in with easy you just punch in your codes did the door and have access to the property. The room had all the amenities and comforts you would need where stay in Key West. The Linens were clean and the bathroom was very spacious. In the kitch...

Stayed Nov 2020

Pertfect Old Town Key West Gem

Quaint , clean and close to everything we want to do. We walked everywhere. All essentials were there, linens, coffee maker, toastier and just enough kitchen gadgets. The only drawback was a crappy cable company, ( difficult to use remote and change...

Stayed Oct 2020

Place is close to everything.

Although the location was great, there should be a couple of things we always had at other guest places. -there were filters, coffee maker but no coffee. All creamer was hardened and unusable. TVs didn’t work properly. I know it was a vaca but who ...

Stayed Oct 2020

Very quiet and quaint cottage

We had a bit of trouble finding it. We were going off of an old address for the check in box. But with a quick text to the property owner, she sent me the correct address and also updated her email straight away, so no one should have any problems in...

Stayed Oct 2020

Truman Annex Perfection!

The property location & quality perfect. Just blocks from all the action of Key West downtown, but far enough away to have relaxing time. Everything about the condo was A-1, beds comfortable, deck shaded & quiet, & furnishings very beachy. Keith the ...

Stayed Sep 2020

Loved the Bali Hideaway!

This was our first time visiting Key West and we fell in love. This amazing little condo certainly helped! It looks exactly like the photos. It is a calming, serene space with island vibes. The privacy is wonderful and it's literally STEPS from the m...

Stayed Sep 2020

Best location for a weekend getaway

Beautiful place, located close to the southern most point, quick walk to everything, the property is very nice, the shared pool is great and you have a privacy. The beds were really comfy and everything was really nice and clean. The automated check ...

Stayed Aug 2020

vacation

the property is located in a perfect location. it is close to the main shopping / tourist area a quick drive to all the beaches. the pool was clean and well maintained. a couple issues came up and the management was quick to respond and help us we wi...

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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.