Historic Seaport holiday lettings

We found 1,202 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Historic Seaport by choosing from 79 houses, 82 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.
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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 type of holiday rental, with around 36 available throughout the area. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces for dining or relaxation, making them ideal for families or groups wanting to enjoy the local charm. Additionally, there are about 12 condos and several apartments and cottages, providing a variety of options for different preferences.
Are there any beach house rentals in Historic Seaport?
In Historic Seaport, there are about 22 beach house rentals available, offering a charming escape near the waterfront. These properties typically feature spacious living areas, fully equipped kitchens, and outdoor spaces where guests can relax and enjoy the coastal atmosphere. Many rentals are located close to key attractions such as the bustling docks, historic sites, and local dining options.
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 fully equipped kitchens, which allow guests to prepare their own meals, and private decks or patios for enjoying the pleasant Florida weather. Many properties also feature coffee and tea makers for that morning brew, along with balconies that offer scenic views of the surrounding area. Onsite parking is a convenient option for those travelling by car.
Can I find family house rentals in Historic Seaport?
In Historic Seaport, Florida, there are around ten family-friendly house rentals available, ideal for those travelling with children. This area is renowned for its vibrant maritime atmosphere and proximity to several attractions. Many homes offer spacious living areas, full kitchens for preparing family meals, and outdoor spaces great for relaxation or play.

Visitors can enjoy easy access to nearby highlights such as the Key West Aquarium and the lively waterfront, where families can explore shops and dine at local restaurants. Furthermore, these properties typically come equipped with modern amenities like Wi-Fi and air conditioning to ensure a comfortable stay.
Can I rent a holiday home with a pool or hot tub in Historic Seaport?
In Historic Seaport, Florida, there are around 13 holiday homes available for rent that feature pools, along with several options that include hot tubs. This charming area, known for its picturesque marina and vibrant setting, offers a variety of properties to suit different preferences. Many rentals come equipped with private pools, providing a great spot for relaxation after a day of exploring the local sights.

Travellers can expect amenities such as spacious living areas, fully equipped kitchens for home-cooked meals, and outdoor spaces that often include sun decks or patios, ideal for enjoying the warm Florida weather. Some properties also feature hot tubs, great for unwinding in the evenings.
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.
Can I book pet-friendly holiday rentals in Historic Seaport?
In Historic Seaport, Florida, there are several pet-friendly holiday rentals available for those travelling with furry companions. Many of these rentals offer convenient amenities such as fully equipped kitchens, outdoor spaces for relaxation, and comfortable living areas to ensure a pleasant stay. Guests can expect properties with features like private balconies or patios, allowing pets to enjoy the warm Florida weather alongside their owners.

The area is rich in maritime charm, and visitors can explore nearby parks and waterfront spaces where pets are welcome. The scenic surroundings of the Historic Seaport make it an ideal base for enjoying both the vibrant local culture and outdoor activities with pets.
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?
The best time to visit Historic Seaport is during its peak season, which runs from January to March. This vibrant period attracts a multitude of travellers eager to experience the area's stunning waterfront and rich history. March, in particular, stands out as a popular month, offering pleasant temperatures that typically hover between 15 to 25 degrees Celsius. This makes it an ideal time for outdoor activities such as sailing, fishing, and leisurely strolls along the marina.

Visitors during this time can enjoy a host of events and festivals celebrating the local culture, all while taking in the beautiful coastal views. The warm weather invites exploration of nearby attractions, ensuring there's never a dull moment.

If you're looking for a more budget-friendly option, consider visiting in October. This month sees fewer tourists, allowing for a more relaxed atmosphere while still enjoying the picturesque scenery and local charm. The temperatures remain mild, making it comfortable for sightseeing and engaging in outdoor adventures without the usual crowds.
Are there any remote work holiday rentals in Historic Seaport?
In Historic Seaport, Florida, there are approximately 60 remote work-friendly holiday rentals available, making it an excellent choice for those looking to blend work and leisure. Many of these properties come equipped with essential amenities such as free Wi-Fi, dedicated workspaces, and comfortable desks, ensuring a productive environment while enjoying your stay.

The Historic Seaport area itself is vibrant, featuring charming waterfront views, seafood restaurants, and easy access to local attractions like the Key West Historic District. This neighbourhood offers a rich blend of history and culture, superb for unwinding after a day of remote work. 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, Florida, United States of America?
In Historic Seaport, Florida, visitors can immerse themselves in the vibrant maritime culture and history of the area. One of the top attractions is the Key West Shipwreck Museum, which offers fascinating exhibits on the shipwreck salvage industry and breathtaking views from the lookout tower. The area is also home to the iconic Mallory Square, known for its lively sunset celebrations featuring street performers and local artisans.

Adjacent to the seaport, the Ernest Hemingway Home and Museum provides insights into the life of the renowned author, set in a beautiful historic building surrounded by lush gardens and six-toed cats. For those interested in marine life, the nearby Key West Aquarium showcases a variety of sea creatures native to the Florida Keys.

Additionally, the Historic Seaport offers easy access to the beautiful waterfront, where visitors can enjoy activities such as boating, fishing, and dining at waterfront restaurants that highlight fresh seafood and local cuisine.
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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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