Historic Seaport, Key West Vacation Rentals: condo and apartment rentals & more

Discover a selection of 1,000 vacation rentals in Historic Seaport, 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 $104 per night, and condos and houses are popular options for a stay in Historic Seaport. Either way, you'll find a rental for everyone's needs.

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Find the best place to stay — Historic Seaport

Search 910 vacation rentals

Stayed Jun 2021

REPLACE THE COUCH…for the love of god!!

Cons: For years now reviews have been mentioning the pullout couch and how bad it is. Well I stayed two years ago and it was horrible for another couple w us that had to sleep on a 3” thick worm out pull out w bars in their backs. Just stayed and st...

Stayed Jun 2021

Perfection

This property was perfect in almost every way! The location can’t be beat. It sits off the road, down a beautiful path, with a lush yard that provides total privacy. It’s within walking distance to Mallory Square, Duval, restaurants, bars, shops, and...

Stayed Jun 2021

Great location and very nice house for couple and two kids.

Very nice, almost ideal rental. Small rant that most rentals, including this one, want you to vacate by 10AM which is too early, especially when they don't let you arrive until after 4. Four hours to clean up should be plenty of time. Also they want ...

Stayed Jun 2021

FAMILY CELEBRATION

Perfect little place and great location to gather for a family celebration. Clean unit, fun little back yard pool area, and quaint location close to all the Duval Street fun! Accommodations just enough to spend family time in or go out every day and ...

Stayed Jun 2021

Private but near everything

Clean, comfortable historic building all to ourselves, short walk to Mallory Square, one block off Duval. We took a taxi from the airport and walked the entire week! There’s plenty of parking for a car though, are at restaurants and cooked some meals...

Stayed Jun 2021

Wonderful Location

We had a wonderful time staying in the home. Mary was very good about responding anytime we needed anything. The only downfall was that the air-conditioning went out while we were there and the repair men spent most of the day (our last day there) re...

Stayed May 2021

Perfect Stay for a Family Vacay!!

The house was beautiful and fit our family of 6 adults perfectly! It was clean and beautiful and truly had the Key West vibe we were hoping for. The pool and the landscaping were a dream. What a wonderful place to have as the setting for my husband a...

Stayed May 2021

Oh my goodness......

Ed was awesome, his condo is off the charts, lots of room, in the heart of Old Town. The roof top deck was amazing, sunsets from the deck and a view of the whole city. Close to the marina and within walking distance of Duval. This is the best place I...

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How many vacation rentals are available around Historic Seaport, Key West?

Our 2021 property listings offer a large selection of 910 vacation rentals around Historic Seaport. From 364 condo and apartment rentals to 448 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Historic Seaport?

Vrbo offers a large selection of vacation rentals near lovely places in Historic Seaport. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

Schooner Western Union: 1,834 vacation rentals
Mallory Square: 1,819 vacation rentals
The Oldest House - Key West: 1,828 vacation rentals
Audubon House and Tropical Gardens: 1,819 vacation rentals
Red Barn Theater: 1,834 vacation rentals

But there are many other points of interest around Historic Seaport 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 Condos/Apartments in Historic Seaport?

Yes, of course. Vrbo has 364 Condos/Apartments in Historic Seaport. Our other popular types of vacation rentals in Historic Seaport include:

Houses: 448 rentals available
Cottages: 66 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 Historic Seaport?

Yes, you can select your preferred vacation rental with pool among our 699 vacation rentals with pool available in Historic Seaport. Please use our search bar to access the selection of vacation rentals available.