Historic Seaport holiday lettings

We found 1,221 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Historic Seaport by choosing from 85 houses, 85 apartments and other holiday rentals. Whether you’re travelling with friends, family or even pets, holiday homes have the best amenities for spending time at your holiday home, which might include cable TV and a washer and dryer. You'll be able to choose a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Historic Seaport

Showing deals for:30 Jan - 6 Feb

Image gallery for 1 Block to Duval St | Banana's Foster Guesthouse

Plunge pool and courtyard
10 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)

1 Block to Duval St | Banana's Foster Guesthouse

Key West, FL

8% off
Price is £18,739
for 7 nights, 1 home
£2,677 per night
includes taxes & fees
1 Block to Duval St | Banana's Foster Guesthouse

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Frequently asked questions

What is the most popular type of holiday rental in Historic Seaport?
In Historic Seaport, holiday houses are the most popular rental option, with around 11 available throughout the area. These spacious properties often feature multiple bedrooms, fully equipped kitchens, and outdoor spaces that are superb for enjoying the warm Florida weather. Many are situated close to the waterfront and local attractions, providing easy access to the picturesque harbour and vibrant dining scene. Condos are also a popular choice, with about 10 on offer, typically featuring modern amenities like pools, fitness centres, and convenient locations near shopping and entertainment. Additionally, several apartments and cottages can be found, providing more intimate settings for travellers seeking a cozier experience.
Are there any beach house rentals in Historic Seaport?
In Historic Seaport, Florida, there are approximately 22 beach house rentals available, providing a charming selection of accommodations near the waterfront and vibrant local attractions. These holiday homes typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor patios or balconies that allow guests to enjoy the pleasant coastal climate. Many properties are conveniently located close to points of interest such as the Key West Historic District and the bustling marina, making it easy for visitors to explore shops, restaurants, and cultural sites.
How much does it cost to rent a holiday home in Historic Seaport?
Prices for holiday rentals in Historic Seaport vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Historic Seaport to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Historic Seaport holiday house rentals?
You can find great discounts on house rentals in Historic Seaport on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Historic Seaport?
In Historic Seaport, popular rental amenities include heated pools, patios, and shared pools, making for a relaxing stay in this charming area of Florida. Many properties also come equipped with kitchens, allowing guests to prepare their own meals.
Are there any family house rentals in Historic Seaport?
In Historic Seaport, Florida, there are numerous family-friendly house rentals available, with around twelve options to choose from. This vibrant area is known for its charming streets and proximity to the water, making it an excellent choice for families looking for a memorable getaway. Many of these properties provide spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces ideal for family activities.
Can I rent a holiday home with a pool or hot tub in Historic Seaport?
In Historic Seaport, Florida, there are plenty of holiday homes available for rent, with around 22 options that feature pools, and several that include hot tubs. This picturesque area is known for its charming waterfront views and vibrant marina atmosphere, making it a delightful choice for travellers looking to enjoy a relaxing getaway.
Are there any Historic Seaport holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Historic Seaport with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there pet-friendly holiday rentals in Historic Seaport?
In Historic Seaport, travellers can find several pet-friendly holiday rentals that cater to their needs while enjoying the charm of this unique area. Many of these properties are equipped with spacious living areas, fully stocked kitchens, and outdoor spaces, allowing pets to roam freely and families to relax comfortably.
Can I find long-stay holiday rentals in Historic Seaport?
A long-stay holiday rental in Historic Seaport is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Historic Seaport for a holiday rental?
March is the most popular time to visit Historic Seaport, attracting travellers eager to soak up the vibrant atmosphere of this charming destination. The peak season runs from January to March, when visitors flock to enjoy the warm, sunny weather and the variety of outdoor activities available. With average temperatures in the comfortable low 20s Celsius, it's an ideal time for exploring the stunning waterfront, embarking on sailing adventures, or simply lounging by the beach.

During this peak season, you'll find plenty of opportunities for sightseeing, from historic landmarks to lively local markets. The area is buzzing with energy, making it superb for those looking to engage in the community vibe and participate in seasonal events.

For those who prefer a quieter experience, consider visiting in October, when the tourist crowds have thinned out. This month offers a wonderful chance to enjoy the cooler temperatures, typically in the mid-teens Celsius, while still having access to beautiful coastal views and fewer crowds, allowing for a more relaxed pace to your holiday.
Are there any remote work holiday rentals in Historic Seaport?
In Historic Seaport, Florida, there are numerous remote work-friendly holiday rentals available, with around 24 properties suiting the needs of those working while travelling. Many of these rentals come equipped with essential amenities such as reliable Wi-Fi, dedicated workspaces including desks and chairs, and comfortable living areas to ensure productivity. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Historic Seaport holiday rental?
Book your Historic Seaport holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Historic Seaport?
In Historic Seaport, Florida, visitors can engage in a rich maritime history and vibrant culture. The area is home to the famous Key West Historic Seaport, where you can stroll along the waterfront and enjoy views of the moored boats while dining at waterfront restaurants. Nearby, the Ernest Hemingway Home and Museum offers a glimpse into the life of the famed author, surrounded by beautiful gardens and historic architecture.
Can I change or cancel my Historic Seaport home rental booking on Vrbo?
To find Historic Seaport holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Historic Seaport holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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