Historic Seaport, Key West Vacation Rentals: house rentals & more

Find the perfect place for your stay in Historic Seaport by choosing from 186 houses, 89 apartments, and other vacation rentals. Whether you’re traveling with friends, family, or even pets, vacation homes have the amenities you need and want for your stay, which might include WiFi and a fireplace. You'll be able to choose a rental to meet everyone's needs, including options that are accessible or non-smoking.

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Find properties near top attractions in Historic Seaport

Mallory Square

Find the best place to stay - Historic Seaport

LA CASITA EN CIMA @ OLD TOWN Quaint Cottage By Duval + LAST KEY SERVICE...

Sleeps 6 · 2 bedrooms · 2 bathrooms

Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

Sleeps 2 · 1 bedroom · 2 bathrooms

Lazy River Pool, Enchanting Garden, Old Town Key West, Free WiFi, Bikes & Parkin

Sleeps 4 · 2 bedrooms · 2 bathrooms

Top rated rentals - Historic Seaport

Great Stay

Amazing location, close to everything but somehow still quiet. Had everything that you’d need, very tropical atmosphere. Would definitely stay again!

Brian R.

Stayed Sep 2023

Cute little cottage

This is a cute place and it is close to everything. We parked the car and then walked to everything we wanted to do. Small for 4 but was fine for a couple day stay. Would definitely stay here again!!

Amy N.

Stayed Jul 2023

Beautiful mansion

This property and room where great . It had everything you needed and was clean The location was absolutely great. Near to all restaurants and shopping. You can park your car and walk to it all or rent a scooter next door and get around town with no worries of parking. We will be back again and would recommend to anyone that wants to visit key west . Thank you for a great place

david q.

Stayed Jul 2023

Absolutely amazing

My fiancé and best friend stayed here for an entire week while celebrating a birthday. I could say 101 things about this place and the hospitality that was given while here. They accommodated everything that we needed and we were able to have a great mix of alone time and time and on the town. The experience itself is so worth it. It was relaxing and beautiful. They went out of there way each day to get us to and from the boat and would definitely stay here again. Thank you so much!

Jacob W.

Stayed Jun 2023

Best anniversary trip!

The suite was comfortable and in the absolute best location. We enjoyed the beautiful gardens and pool in the evenings after a fun day of exploring the island. We whole-heartedly recommend!

Debbie H.

Stayed Jun 2023

Quiet and relaxing stay on Fleming Street

The unit was very nice and comfortable and had all the amenities needed to have an enjoyable stay. The courtyard and pool was such a nice and relaxing area. This unit was on a very quiet street, but still very close to all the action. Everything was within walking distance. We would stay here again as well as recommend it to others.

Sara B.

Stayed May 2023

Love this condo!

This was a nice place to stay for a change from the resorts. I would highly recommend. There is no view with this unit, but the pool makes up for it. Several units share the pool but there was no one using it the whole week we were there so it felt like a personal pool to us. A little of a hassle to go pick up keys and return at different location (rental company) but they have after hours pick up and drop off if needed. If this were the only time going to Key West, I might recommend somewhere with more of a view but we go often and just wanted a change. It was perfect for what we were looking for!

Kristy J.

Stayed Apr 2023

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Frequently asked questions

How many vacation rentals are in Historic Seaport?

Our current selection of vacation homes in Historic Seaport is ${propertiesCount}. All it takes is a simple Vrbo property search to book your next villa, condo, house or whatever kind of vacation rental that suits you.

What is the most popular type of vacation rental accommodation in Historic Seaport?

Based on our data, condos are considered the most popular type of vacation property in Historic Seaport. But that goes without saying, everyone's idea of an epic stay isn't going to be the same. Vrbo has vacation rentals with every shape, size and budget in mind, and we'll help you to find the perfect fit.

How much does it cost to rent a vacation rental in Historic Seaport?

Season, property type and length of stay are some of the conditions that can affect the price of a vacation home. Simply enter your dates of travel to find your dream escape. From comfy cottages to sprawling luxury villas, all Vrbo vacation rentals provide unbeatable value.

How much does it cost to rent a beach house in Historic Seaport?

When you travel and the size and style of the property will influence the cost of your beachside stay. Type in your Historic Seaport travel dates to see your options on Vrbo. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use the filters to pick the features and amenities you want.

Are there pet-friendly vacation rentals in Historic Seaport?

Good news! Yes. You'll have your pick of 298 vacation rentals that cater to pets in Historic Seaport. Some of our pet-friendly vacation rentals even have an area outdoors for your four-legged friend to play around in, complimentary treats, doggie beds and proximity to parks and green space. Apply the 'Pets allowed' filter to find a pad that'll set tails wagging on Vrbo.

Can I rent a house with a pool in Historic Seaport?

Add an extra layer of fun to your trip by booking your group into one of the 256 houses with a private pool in Historic Seaport. Use our search filter to find the kind of property you want on Vrbo, and then spend carefree days splashing about in a swimming pool that's for your use only.

What are popular rental amenities in Historic Seaport?

The most popular rental amenities people are searching for in Historic Seaport include nearby museums, a fireplace and a barbecue grill. Whether you're hitting the road with buddies, family or even pets, Vrbo vacation homes feature the best amenities for ultimate relaxation with the people you cherish the most.

Are there large group vacation rentals in Historic Seaport?

With 32 properties that can sleep 10 or more people in Historic Seaport, you don't have to limit the invite list. From fun family vacations to events like Christmas or New Year's Eve parties, Vrbo will help you find a large group rental to match the occasion.

Are there vacation rentals in Historic Seaport that welcome kids?

Historic Seaport has 297 family-friendly vacation rentals. And booking a stay that welcomes little ones is a cinch with our "Properties good for families" filter. On top of having the entire place to yourselves, you'll get access to perks and amenities such as multiple bedrooms, kitchens and yards.

What are the top attractions for families in Historic Seaport?

Keep the kids happy at these leading family-friendly attractions in Historic Seaport:

Key West Aquarium
Mel Fisher Maritime Museum
Florida Keys Eco - Discovery Center

Are there one-bedroom vacation rentals in Historic Seaport?

There are 99 one-bedroom properties in Historic Seaport to choose from. A one-bedroom vacation rental is a wonderful option if it's only two of you or if you're traveling on your own. Toss in more convenience, privacy and space compared to a hotel, and you're sure to have an unforgettable break.

Can I find two-bedroom vacation rentals in Historic Seaport?

Historic Seaport has 90 two-bedroom vacation rentals to select from. Experience a vacation home with all the privacy and space you need at a price you'll love on Vrbo.