Vacation Homes in Historic Seaport, Key West: House Rentals & More

Find the perfect place for your stay in Historic Seaport by choosing from 165 houses, 81 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.

Vacation rentals with weekly discounts - Historic Seaport

Showing deals for:Sep 5 - Sep 12

Wonderful

(64 reviews)

ShangriLa Suite / Queen Studio / Sleeps 2

Key West, FL

8% off

per night

All fees included

Galley style kitchen, full frig, ice maker, microwave, cooktop, granite counters

Exceptional

(34 reviews)

'LA DOLCE VITA' OLD TOWN, STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!

Key West, FL

7% off

per night

All fees included

Nice size pool with plenty of sitting areas and lounge chairs.

Exceptional

(126 reviews)

Historic District-Pool View-Duval Street-Beach Nearby-No Contact Check-In

Key West, FL

8% off

per night

All fees included

Exceptional

(116 reviews)

Prime location, stunning views from 2 decks—walk or ride to explore the island!

Key West, FL

8% off

per night

All fees included

This home is one of the most photographed homes in Key West. It's a quintessential Conch house in an incredible location.

Exceptional

(8 reviews)

Just steps to Duval- Sleeps 10- Pool House

Key West, FL

9% off

per night

All fees included

Wonderful

(194 reviews)

DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!

Key West, FL

8% off

per night

All fees included

Did someone say "hot tub time?" Enjoy a space to dine, chill, or catch some sun on the sun porches and patios.

Exceptional

(16 reviews)

Near Duval: Hot Tub, Sleeps 6, Top Location

Key West, FL

9% off

per night

All fees included

Exceptional

(143 reviews)

"LA DOLCE VITA", OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!!

Key West, FL

8% off

per night

All fees included

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Historic Seaport

Mallory Square

Find the best place to stay - Historic Seaport

Underwater Cabana at Custom House Inn | Right In The Heart, On Duval!

Sleeps 4 · 1 bedroom · 1 bathroom

Grand Bahama suite-3 bedroom 2 bath, a block off Duval St w/pool, parking

Sleeps 8 · 3 bedrooms · 2 bathrooms

Top rated rentals - Historic Seaport

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Frequently asked questions

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

Apartments are the most popular type of vacation rental in Historic Seaport, according to our data. Even if you’ve got a different idea about what you want, Vrbo has vacation homes in loads of sizes and shapes. Filter our options to find your perfect Historic Seaport pad.

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

Several factors can determine what you’ll pay for your vacation rental in Historic Seaport, including the time of year, length of stay and property type. Still, all Vrbo homes have something in common — unbeatable value. Simply enter your travel dates to find your home away from home.

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 help determine the cost of your beachside stay. Enter your Historic Seaport travel dates to see all your options on Vrbo. Did someone just say “hot tub”? Use our filters to pick the amenities and features you need.

Are there pet-friendly vacation rentals in Historic Seaport?

Good news! Yes. You’ll have your pick of 249 vacation rentals that cater to pets in Historic Seaport. Plenty of our pet-friendly vacation rentals come with an area outdoors for your furry pal to have fun in, dog beds, complimentary treats and proximity to parks. Apply the “Pets allowed” filter to find a pad that’ll get tails wagging on Vrbo.

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

Dig out your swimwear and inflatable swan, because there are 205 houses with a private pool in Historic Seaport. Book a stay at one of these terrific vacation homes and every day can be a pool day. Simply enter your dates into Vrbo, then check the “pool” filter to find the ideal place for a splashing good time!

What are popular rental amenities in Historic Seaport?

Some of the most popular rental amenities guests are looking for in Historic Seaport are a lake view, a chef and a nearby waterfront. Whether you’re on a trip with family, your besties or even pets, Vrbo vacation homes come with the best amenities for ultimate relaxation with the people who matter most.

Are there large group vacation rentals in Historic Seaport?

Historic Seaport has 22 vacation rentals that can host 10 or more guests. These properties come with the space and privacy you need to share good times with loved ones.

Are there vacation rentals in Historic Seaport that welcome kids?

With 248 family-friendly vacation rentals available in Historic Seaport, now is a superb time to introduce your little ones to the magic of travel. Simply check our “Properties good for families” filter box to view stays that feature conveniences ideal for families on the move, such as full kitchens, private pools, entertainment areas and hot tubs.

Are there one-bedroom vacation rentals in Historic Seaport?

Historic Seaport has 110 one-bedroom rentals available. Often positioned in popular areas due to their compact size, a one-bedroom rental is perfect if you’re traveling with a buddy or your partner. And with home comforts like air conditioning and more privacy than a standard hotel, you’ll be able to kick back while enjoying this awesome destination.

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

Historic Seaport has 69 two-bedroom vacation rentals to pick from. Find a vacation home with all the privacy and comfort you want at a price you’ll love on Vrbo.

Are there vacation rentals with WiFi in Historic Seaport?

Pick from 78 vacation rentals with WiFi in Historic Seaport. If you’d like to disconnect from the world on your vacation, but still need to be connected to the web, these getaways are just what you need. Narrow your search by applying the WiFi filter on Vrbo.

How can I find vacation rentals with air conditioning in Historic Seaport?

Historic Seaport has 236 vacation rentals where you’ll be able to relax and recharge in air-conditioned comfort. To book a stay on Vrbo featuring this amenity, enter your preferred travel dates and use the filter tool to select the “air conditioning” box.

How old do you have to be to rent a vacation rental in Historic Seaport?

The minimum age is typically 16, 18 or 21. It can vary from property to property on Vrbo, so look at the rules of your preferred Historic Seaport stay before booking.

How long can I rent a vacation rental in Historic Seaport for?

How long you can book a vacation rental in Historic Seaport differs according to the property. Just enter your desired travel dates to look at a list of options offering extended stays. With loads of amenities such as washing machines and kitchens, as well as some offering weekly or monthly discounts, you’re sure to get a terrific place to call your home away from home in Historic Seaport.

Does Vrbo offer discounts for vacation homes in Historic Seaport?

On Vrbo, you’ll find amazing discounts and bargains for Historic Seaport. Browse our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you’re off on a weekend retreat or a much longer stay, Vrbo has lots of options for every style and budget.