Historic Seaport vacation rentals

We found 1,230 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Historic Seaport by choosing from 86 houses, 86 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

  • Picturesque Waterfront: Enjoy stunning views and stroll along the vibrant waterfront, perfect for relaxation and sightseeing.
  • Rich History: Explore historic houses and charming streets that showcase the area's unique past.
  • Exciting Water Excursions: Embark on thrilling boating adventures and water activities available in the area.
  • Family-Friendly Attractions: Visit the Key West Aquarium and other attractions that cater to all ages.
  • Romantic Sunsets: Don't miss the breathtaking sunsets that create a magical atmosphere for couples.

Popular types of accommodation around Historic Seaport

Discover the charm of Historic Seaport with Vrbo's selection of vacation rentals. Whether you prefer a private vacation home, a cozy cottage, or a modern condo, there’s something for everyone. Enjoy a waterfront destination with plenty of parking options, including at the nearby Hyatt Centric Key West Resort. Your perfect getaway awaits.

  • Houses: The top choice for visitors to Historic Seaport, these homes offer spacious and comfortable settings for families or groups seeking a unique stay.
  • Condos: A popular option, condos provide a blend of convenience and amenities, perfect for those wanting a more modern experience.
  • Cottages: Charming and quaint, cottages are ideal for travelers seeking a cozy retreat near the water.
  • Apartments: These versatile rentals offer a home-like feel, perfect for solo travelers or couples exploring the area.
  • Villas: Luxurious and spacious, villas cater to those looking for an upscale experience in Historic Seaport.**

Top attractions near Historic Seaport

Historic Seaport in Key West, Florida, is ideal for city-themed, family, or business vacations. Visitors can explore historic houses, charming streets, and modern squares while enjoying a vibrant culture and outdoor experiences. Don't miss the picturesque waterfront, water excursions, and the Key West Aquarium to enhance your visit. This charming area offers a delightful mix of attractions that cater to all types of travelers looking to soak in the local history and scenery.

  • Duval Street: A vibrant and bustling street, Duval Street is famous for its lively atmosphere, filled with shops, bars, and restaurants. It is the perfect place to experience the local nightlife and enjoy the laid-back island vibe.
  • Mallory Square: Known for its stunning sunset views, Mallory Square is a gathering place for street performers and local artisans. The lively atmosphere makes it an ideal spot to relax and soak in the energy of Key West.
  • Ernest Hemingway Home and Museum: Step into the world of the legendary author at his former residence. The museum showcases Hemingway's life, works, and beautiful gardens, offering a glimpse into the culture and history of the area.

Things to do recommended for couples

Planning a romantic getaway in Key West? Explore the charming Historic Seaport with a sunset sail, savor a candlelit dinner at a waterfront restaurant, or take a leisurely stroll along the vibrant streets. Don’t forget to capture the stunning sunset at Mallory Square for a perfect ending.

Things to do recommended for families

Families can take a refreshing dip at the MLK Community Pool & Community Center, located 0.8 miles from Historic Seaport. With its family-friendly atmosphere and outdoor sports options, it's a perfect spot for relaxation and fun after exploring the vibrant local area.

Things to do recommended for groups

Groups visiting Historic Seaport can enjoy a round of golf at the nearby Key West Golf Club, take in a show at the Waterfront Playhouse, or shop for unique souvenirs at The Kite House, all while soaking up the vibrant local culture and atmosphere.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

When traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your filters effectively. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Historic Seaport with a group: Think about how many bedrooms you’ll require, along with features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Historic Seaport with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, keeping in mind your closeness to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Historic Seaport: For many families, a vacation isn’t truly fulfilling without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Many of these 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 offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Historic Seaport

Exploring Historic Seaport in Key West, Florida, promises a delightful blend of tropical charm and rich history. Whether you’re strolling along the vibrant waterfront or indulging in family-friendly activities, this area offers a unique Key West experience. Don’t miss the chance to enjoy romantic sunsets, embark on exciting excursions, and soak in the local culture. With its captivating atmosphere, Historic Seaport is the perfect starting point for your unforgettable trip to Key West.

  • Key West: As the southernmost city in the continental United States, Key West is renowned for its vibrant atmosphere and stunning natural beauty. The Historic Seaport serves as its focal point, where visitors can enjoy a variety of family-friendly activities, from sailing and fishing to shopping in unique boutiques. The city's laid-back vibe is perfect for those wanting to relax on the beach or explore the lively streets filled with bars and restaurants. Don't miss the iconic sunset celebrations at Mallory Square, where street performers and local artisans come together to create a festive ambiance.
  • Old Town Key West: Located a mere 0.6 miles from the Historic Seaport, Old Town Key West is a charming neighborhood that captures the essence of island living. Known for its picturesque streets and historic architecture, this area is perfect for strolling and discovering local shops and cafes. Families and business travelers alike will appreciate the relaxed atmosphere, with nearby attractions such as beaches and parks. Be sure to visit the famous Ernest Hemingway Home and Museum to delve into the literary history of the area and enjoy the lush gardens that surround it.
  • Key West Historic District: Just 0.4 miles from the Historic Seaport, the Key West Historic District offers a glimpse into the island's rich history. This neighborhood is characterized by its well-preserved 19th-century architecture and vibrant streets filled with art galleries and boutique shops. Visitors can immerse themselves in the local culture by exploring the nearby beaches and enjoying family-friendly activities. The area is also home to several historical landmarks, including the Key West Lighthouse and the Harry S. Truman Little White House, making it a must-visit for history buffs.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 a breeze

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner has its perks. By joining our travel rewards program, One Key, you can immediately access member discounts and earn or redeem OneKeyCash on eligible reservations. Sign up now and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board is designed to help you plan your travels with ease. Whether you're starting a new trip, refining your plans, or reviewing your existing bookings, this feature organizes your saved or booked properties into categories: Potential Trips, Upcoming Trips, and Current Trips. To dive into your Trip Boards, simply visit: https://www.vrbo.com/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 about 11 available throughout the area. These homes provide spacious rooms, often featuring multiple bedrooms, fully equipped kitchens, and outdoor spaces for enjoying the tropical climate. Additionally, there are around 10 condos available, which typically include modern amenities such as pools and fitness centers, offering a more resort-style experience. Apartments and cottages are also present, although in smaller numbers, providing travelers with more intimate and cozy options.
Are there any beach house rentals in Historic Seaport?
In Historic Seaport, Florida, there are about 22 beach house vacation rentals available. These properties are typically located near the vibrant waterfront, offering easy access to local attractions such as the Key West Historic District and the lively Duval Street. Travelers can expect amenities like spacious layouts, fully equipped kitchens, and outdoor spaces such as patios or balconies superb for enjoying the tropical climate. Many beach houses also feature private pools and easy access to the beach, making them ideal for families and groups looking to relax and unwind by the water.
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 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 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 heated pools, patios, and fully equipped kitchens, suiting travelers looking for comfort and convenience. Many rentals also feature shared pools, allowing guests to enjoy a refreshing swim while socializing with others.
Are there any family house rentals in Historic Seaport?
In Historic Seaport, Florida, there are some available family-friendly house rentals that cater to groups looking for a memorable getaway. This charming area is known for its vibrant waterfront, making it an ideal spot for families to explore. Many of the homes provide spacious living areas, full kitchens for preparing meals together, and outdoor spaces where children can play and enjoy the sunshine.

Visitors can easily access nearby attractions, including the bustling local markets and various dining options that offer fresh seafood and regional specialties. Additionally, the proximity to the scenic waterfront allows for fun activities such as boat tours and fishing excursions, enhancing the overall experience for families.
Can I rent a vacation home with a pool or hot tub in Historic Seaport?
In Historic Seaport, Florida, travelers can find a variety of vacation homes available for rent that feature both pools and hot tubs, with around 22 options to choose from. This charming area is known for its rich maritime history and vibrant atmosphere, making it a delightful destination for a getaway. Many of the rentals come equipped with private pools and hot tubs, providing guests with opportunities for relaxation after a day of exploring the local sights.

Expect amenities such as spacious outdoor areas, fully equipped kitchens, and comfortable living spaces, ideal for families or groups seeking both comfort and convenience.
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 travelers 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 vacation rentals in Historic Seaport?
In Historic Seaport, Florida, there are several pet-friendly vacation rentals available, offering a charming experience for travelers with pets. Many of these rentals come equipped with amenities such as fully stocked kitchens, outdoor spaces, and comfortable living areas, making them ideal for families or groups.

The area itself is known for its vibrant maritime culture, and visitors can enjoy close proximity to the waterfront, where scenic walks and beautiful views abound. Additionally, the nearby parks and beaches provide great spots for outdoor activities with pets, ensuring a delightful stay for both travelers and their furry companions.
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. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Historic Seaport for a vacation rental?
March is the most popular time to visit the Historic Seaport in Florida, drawing in travelers eager to bask in the beautiful weather and vibrant atmosphere. The peak season spans from January to March, characterized by pleasant temperatures and a bustling tourist scene. During this time, visitors can enjoy outdoor activities such as boating, fishing, and exploring the charming waterfront, all while surrounded by the stunning coastal views that the Seaport is known for.

In March, temperatures typically range from the mid-60s to the low 80s Fahrenheit, making it an ideal time for outdoor sightseeing and leisurely strolls along the docks. Whether you're indulging in fresh seafood at local eateries or soaking in the lively ambiance of the nearby markets and shops, the experience is sure to be memorable.

For travelers seeking a more budget-friendly option, consider visiting in October. This month offers a quieter atmosphere while still providing pleasant weather, allowing for exploration of the Seaport's historical sites and natural beauty without the high-season crowds. You can enjoy fishing, kayaking, or simply relaxing by the water, all while taking in the idyllic surroundings.

Ultimately, the best time to book a vacation rental in Historic Seaport depends on your preference for lively interactions and activities during peak season or a more tranquil experience in the shoulder months.
Are there any remote work vacation rentals in Historic Seaport?
In Historic Seaport, Florida, travelers will find a variety of remote work vacation rentals—around 24 options available in the area. Many of these properties cater to remote workers, providing essential amenities such as high-speed Wi-Fi, dedicated workspaces with desks and chairs, and comfortable office setups. This makes it convenient for those looking to blend work and leisure while enjoying the charming coastal atmosphere.

The Historic Seaport area is rich in culture and history, with easy access to local points of interest like the Key West Historic District and the waterfront. Rentals in this region often feature spacious living areas, fully equipped kitchens, and outdoor spaces where guests can unwind after a busy day. 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?
In Historic Seaport, Florida, visitors can explore several captivating attractions. The waterfront area is home to the bustling marina where you can admire a variety of boats and yachts, and it's an excellent spot for dining and nightlife. Nearby, the Ernest Hemingway Home and Museum offers a glimpse into the life of the famous author, complete with beautiful gardens and the iconic six-toed cats.

The Mel Fisher Maritime Museum is also a must-visit, showcasing fascinating artifacts from shipwrecks and providing insights into the area's rich maritime history. For those who enjoy outdoor activities, the nearby Fort Zachary Taylor Historic State Park features a sandy beach and hiking trails, superb for a day of relaxation and exploration.
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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, 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 organizing 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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