Historic Seaport vacation rentals

We found 1,151 vacation rentals — enter your dates for availability
Find the perfect place for your stay in Historic Seaport by choosing from 80 houses, 54 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 out more about Historic Seaport

Why visit Historic Seaport

  1. Scenic Harbour Walk: Enjoy a leisurely stroll along the picturesque Key West Harbour Walk, soaking in the waterfront charm and vibrant local culture.
  2. Rich History: Explore historic houses and sites that reflect the captivating history of Key West.
  3. Family-Friendly Activities: Engage in various activities suitable for all ages, highlighting the tropical atmosphere of the area.
  4. Cultural Excursions: Dive into the local culture with unique excursions throughout the Key West Historic District.
  5. Charming Accommodations: Stay in delightful vacation homes, condos, or cottages that offer a taste of Old Key West.

Popular types of accommodation around Historic Seaport

Planning a getaway to Historic Seaport? You're in for a treat! Discover a variety of popular accommodations, including houses, condos, and charming cottages. Enjoy the unique charm of Old Key West and relax in beautiful seaport properties. Most rentals offer free Wi-Fi and outdoor seating, ensuring a comfortable stay. Explore your options and find the perfect spot for your memorable vacation!

  • Houses: The top choice for visitors to Historic Seaport, offering spacious and comfortable accommodations perfect for families or groups.
  • Condos: A popular selection, condos provide modern amenities and often stunning views, ideal for a relaxed stay.
  • Cottages: These quaint and charming retreats offer a cozy atmosphere for a peaceful getaway.
  • Apartments: A convenient option for solo travellers or couples, combining comfort and accessibility.
  • Caravan Parks: A family-friendly choice for those seeking a more adventurous and budget-conscious experience.**

Top attractions around Historic Seaport

If you're planning a vacation to Historic Seaport in Key West, Florida, you'll find a perfect blend of culture and family-friendly activities. Explore historic houses, charming streets, and modern squares, all while enjoying scenic walks and boat tours. Don't miss the opportunity to dive into the local culture with excursions in the Key West Historic District. Whether travelling solo or with family, there's something for everyone at this vibrant destination.

  1. Duval Street: A vibrant thoroughfare brimming with lively bars, quirky shops, and diverse dining options. Immerse yourself in the bustling atmosphere while enjoying street performers and local artists.
  2. Mallory Square: A bustling gathering place famous for its stunning sunsets, street performers, and artisan vendors. Enjoy a lively waterfront atmosphere with live music and local food.
  3. Ernest Hemingway Home and Museum: Step into the world of one of America's greatest writers. Explore the lush gardens and historic rooms, offering a glimpse into Hemingway’s life and creativity.

Things to do recommended for families

Families visiting Historic Seaport in Key West can enjoy a refreshing day at the MLK Community Pool & Community Center, located 1.3km away. With its family-friendly atmosphere and outdoor vibes, it's a great spot for kids to swim and play together.

Things to do recommended for groups

Experience the charm of Key West by teeing off at the Key West Golf Club, just 6.4km away, or enjoy a captivating performance at the Waterfront Playhouse, located a mere 322m from the Historic Seaport. Don't forget to explore The Kite House, only 483m away!

What do I need to keep in mind when booking a vacation around Historic Seaport

When planning your trip—whether you're traveling with a group, enjoying time with family, bringing your pets, or seeking extended stays—it's essential to refine your search based on your priorities. Here are some helpful booking tips for Vrbo to assist you.

  • Traveling to Historic Seaport with a group: Think about how many bedrooms you'll require, as well as any amenities like a complete kitchen or outdoor space for group gatherings. The good news is that you can easily refine your search on Vrbo to include all of these options and more.
  • Traveling to Historic Seaport with young kids: Traveling with young children can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Historic Seaport: For many families, a vacation isn’t truly fulfilling without their furry companion by their side. If this resonates with you, we invite you to explore Vrbo listings that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Historic Seaport: If you're in search of vacation rentals that offer discounts for stays of a month or longer, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay around Historic Seaport

Exploring Historic Seaport in Key West, Florida, offers a delightful mix of adventure and romance. Stroll along the picturesque Key West Harbor Walk, where waterfront charm and vibrant local culture come alive. Discover the rich history of the area and indulge in family-friendly activities that highlight the tropical atmosphere. Whether you're seeking excursions or simply relaxing by the water, Historic Seaport promises an unforgettable experience for every traveller.

  • Old Town Key West: Located a mere 966m from Historic Seaport, Old Town Key West is a vibrant neighbourhood that captures the essence of island life. Visitors flock here for its unique blend of city charm, family-friendly activities, and business opportunities. The area is dotted with quaint shops, bustling malls, and luxurious resorts, making it a prime destination for shopping enthusiasts. Explore local landmarks including picturesque streets and family-friendly beaches, where relaxation and fun intertwine to create unforgettable memories.
  • Key West Historic District: Just 644m away from Historic Seaport, the Key West Historic District offers a rich tapestry of culture and history. This neighbourhood is an ideal stop for families and business travellers alike, with an array of shopping areas and resort options. Stroll along its historic streets, where you'll encounter beautiful architecture and fascinating stories of the past. Nearby beaches provide a serene escape, perfect for soaking up the sun or enjoying water activities with loved ones.
  • Downtown Key West: Situated 805m from Historic Seaport, Downtown Key West is the bustling heart of the island. It attracts visitors seeking a lively urban experience, family outings, and business engagements. The neighbourhood boasts a mix of shopping areas and resort facilities, ensuring a convenient stay. Wander through its lively streets, and enjoy access to nearby beaches that cater to all ages, making it an excellent choice for relaxation and recreation.

Best time to go to Historic Seaport

If you're planning a trip to Historic Seaport, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from January to March, while off-peak times, like August to October tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January71.1°F (21.7°C)No Rain (Dry)Mostly SunnySlightly HighAverage
February72.1°F (22.3°C)No Rain (Dry)Mostly SunnySlightly HighAverage
March73.4°F (23.0°C)No Rain (Dry)Mostly SunnySlightly HighSlightly High
April76.8°F (24.9°C)No Rain (Dry)Mostly SunnyAverageSlightly High
May79.3°F (26.3°C)Light RainMostly SunnyAverageAverage
June82.6°F (28.1°C)Light RainMostly SunnyAverageSlightly Low
July84.0°F (28.9°C)Light RainMostly SunnyAverageAverage
August84.4°F (29.1°C)Light RainMostly SunnySlightly LowSlightly Low
September83.7°F (28.7°C)Light RainMostly SunnySlightly LowSlightly Low
October80.8°F (27.1°C)Light RainMostly SunnySlightly LowAverage
November76.6°F (24.8°C)Light RainMostly SunnyAverageAverage
December73.9°F (23.3°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is simple

Are you hoping to save on your upcoming adventure? Being flexible with your travel dates can make a difference, as prices often fluctuate. You might also enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform where you can easily plan new trips, continue from where you last stopped, or manage your travel arrangements. You can view your saved or booked properties organized under Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Historic Seaport?
In Historic Seaport, vacation houses are the most popular type of vacation 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 vacation home in Historic Seaport?
Prices for vacation 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 travelling 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.
Are there any discounts for Historic Seaport vacation 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 vacation home with a pool or hot tub in Historic Seaport?
In Historic Seaport, Florida, there are around 13 vacation 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 vacation rentals with parking?
Vrbo offers a wide selection of vacation 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 vacation rentals in Historic Seaport?
In Historic Seaport, Florida, there are several pet-friendly vacation 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 vacation rentals in Historic Seaport?
A long-stay vacation 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 vacation 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 vacation rentals in Historic Seaport?
In Historic Seaport, Florida, there are approximately 60 remote work-friendly vacation 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 vacation rental?
Book your Historic Seaport vacation 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 vacation 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 vacation 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 vacation 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.

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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