Historic Seaport vacation rentals

We found 1,134 vacation rentals — enter your dates for availability

Welcome to the enchanting island of Key West, where vibrant streets and a rich maritime heritage create an unforgettable escape. Stroll through charming neighborhoods, revel in the lively atmosphere of Duval Street, and capture breathtaking sunsets at Mallory Square. With a variety of accommodations from cozy cottages to luxurious resorts, you'll find the perfect home base for family-friendly adventures and cultural experiences. Embrace the comfort and convenience of a vacation rental, where you can relax and create lasting memories in your own island oasis.

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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.

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 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.

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