Discover a selection of 1,000 vacation rentals in Historic Seaport, Key West that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $159 per night, and houses and condos are popular options for a stay in Historic Seaport. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Historic Seaport
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What are the top vacation rentals in or near Historic Seaport?

Whether you're seeking a cozy retreat for you and your love or a sprawling house to fit family and friends, you'll find some top vacation rentals in and around Historic Seaport. Here are a couple we think you'll like:

  • Around 1 mile from the center of Historic Seaport, you'll find it hard to resist "Key West Oasis, Seperate Cottage". It has 2 bedrooms and a host of amenities including a desk chair and off-street parking options.
  • Alternatively, get comfortable at "Cloud 9 ~ It's Heaven On Earth In This 3b". Around 0.1 miles from the heart of Historic Seaport, it has 3 bedrooms and features tennis and WiFi.

For even more great options, use the search bar at the top of the page to find the perfect Historic Seaport vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Historic Seaport?

If you're longing to relax and completely switch off for a day or two, you'll find a range of fabulous weekend getaways in and near Historic Seaport. Take a well-deserved break at one of these top options:

  • Book a few nights or longer at "Casa Cove Beautiful Tropical Decorated 3 King Suites Pool 2 Mi Beach", around 4 miles to the east of Historic Seaport, and you've got yourself the best kind of weekend escape. You'll have nature hotspots like Simonton Beach and Key West Golf Club nearby and conveniences like a balcony and heating at your fingertips.
  • Another appealing option is "Starfish - Sunny Townhome In Quiet Truman Annex Two Blocks From Duval St", which is around 1 mile south of Historic Seaport. When you're not relaxing in your rental making use of an oven and a nearby marina, be sure to visit Looe Key National Marine Sanctuary and Key West Garden Club.

Can I find studio apartments for rent in and around Historic Seaport?

Studio apartments are tough to beat when it comes to character, convenience and location. Browse these studio apartments for rent in or near Historic Seaport and experience the local culture and vibe:

  • Throw your bags down at "Condo In Old Town Key West's Truman Annex". Amenities including golf and a pool help make guests feel at home here.
  • Alternatively, get into vacation mode at "Your Condo By The Beach With Ocean View", which comes with conveniences such as a nearby laundromat and an oven.

When it's time to leave your studio apartment and cross off the sights, there's loads to keep you on the move around Historic Seaport. Passionate about culture? Visit Studios of Key West and Red Barn Theater.

Can I find short term rentals in or near Historic Seaport?

Just because you only have two or three days free doesn't mean you have to spend it in a dull hotel room. Head off on vacation but still have the home comforts you need at one of these short-term rentals in or around Historic Seaport:

  • "Casa Capri Beautiful Tropical Style House With 3 King Suites Pool 2 Mi To Beach" is near the heart of Historic Seaport, which means there are loads of things to keep you entertained. Discover cool sights like Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens when you're not making the most of your cozy rental.
  • Sleep, eat and explore from "Villa Josine ~ 4 B/4. 5 Ba Large Designer Home With Pool In A Great Location", another popular option. Smathers Beach and Southernmost Point should be on your to-do list when it's time to see the sights.

What are the best romantic weekend getaways in or near Historic Seaport?

Nothing says "I love you" like planning a romantic weekend together. If you're eager to spend a couple of relaxing evenings away with your partner, we've got some romantic getaways in and around Historic Seaport that will set your heart aflutter:

  • Around 1 mile from Historic Seaport, "Key West Oasis, Seperate Cottage" is an ideal place for lovestruck couples. Beauty services and outdoor furniture are just some of the many amenities you'll find here.
  • Another place where you can enjoy a few glorious days together is "Cloud 9 ~ It's Heaven On Earth In This 3b". Located around 0.1 miles from Historic Seaport, air conditioning and a swimming pool add to the atmosphere here.

Are there mansions for rent in or near Historic Seaport?

Nothing screams "Best. Vacation. Evvv-er." like staying in a mansion. Treat your family to an unforgettable escape at one of these mansions for rent in or near Historic Seaport:

  • Charm, style and oodles of character — "Noona's Mansion @ The Annex Grand Home And Pool + Last Key Services" has it all in abundance. Approximately 1 mile southwest of Historic Seaport and offering a swimming pool and golf, this place is difficult to beat.
  • With a swimming pool, golf and plenty of other first-class amenities, "Captiva" ~ , Historic Mansion Suite With Community Pool" will get your guests' tick of approval. This plush retreat is roughly 1 mile to the southeast of Historic Seaport.

What are the best large group vacation rentals in or near Historic Seaport?

Big groups mean huge fun. They also mean finding a place that'll comfortably fit your entire crew. Browse our large group vacation rentals in or around Historic Seaport and get everybody together under one roof:

  • Offering comfort, space and privacy, you'll get your guests' tick of approval at "New Photos: Drive To Your Getaway". Up to 12 people can stay at this retreat which has 5 bedrooms, a swimming pool and a garden. You'll find it around 1 mile to the southeast of Historic Seaport.
  • "William Skelton Home - Heart Of Key West" is another fantastic option. It's around 0.1 miles to the southwest of Historic Seaport, has 6 bedrooms and sleeps as many as 14 guests. A swimming pool and a garden are among the things designed to make your visit even more memorable.

What are the best houses for rent with a pool in or near Historic Seaport?

A pool is often an essential amenity for any unforgettable vacation. Enjoy frolicking around or simply kicking back by the water at one of these rejuvenating escapes in or near Historic Seaport:

  • Make pool day every day at "Casa Capri Beautiful Tropical Style House With 3 King Suites Pool 2 Mi To Beach". A toaster and a dishwasher are a few of the other amenities that help make this place a favorite.
  • Alternatively, stay at "Casa Cay West Beautiful Tropical House 3 Bedrooms 2 King Suites Pool 2 Mi Beach" and spend your trip poolside. Books and a living room are other things your crew will like about this rental.

What are the best large family vacation rentals in or near Historic Seaport?

Every family catch-up should be one to remember. Whether you're organizing a break with the kids or a reunion with the extended family, our large family vacation rentals in or near Historic Seaport offer a comfy home away from home with ample space for everyone:

  • Sleeping as many as 7 guests in 3 bedrooms, "Cloud 9 ~ It's Heaven On Earth In This 3b" is the perfect place for some family time. This escape is 0.1 miles to the south of Historic Seaport and has creature comforts that include a kitchen and a balcony.
  • "Casa Cove Beautiful Tropical Decorated 3 King Suites Pool 2 Mi Beach" is also popular with families. It's about 4 miles to the east of Historic Seaport, has 3 bedrooms and can accommodate up to 8 people. Useful amenities here include a garden and a stair gate.

If you'd love to sightsee, there are loads of family-friendly attractions nearby to add to your to-do list. Duval Street, Key West Aquarium and Key West Wildlife Center are excellent places to start.

Can I find family cabin rentals in or near Historic Seaport?

Cozy up with your kiddos in a family cabin rental in or near Historic Seaport and get set to make some incredible new memories together. Here's just a taste of what we've got:

  • "Cabin - Orange Blossom Suite | 1 Bedroom 1 Bath In Steps Off Duval" - Enjoy great times with your nearest and dearest at this escape, which is around 1 mile south of central Historic Seaport. A TV and a swimming pool are some of its family-friendly amenities.
  • "Cabin - Hidden Treasure - 2 Bedroom 2 Bath With Shared Pool" - This cabin is another family favorite and is around 1 mile southeast of Historic Seaport. Offering a kitchen, a fridge and more, it'll get your group's nod of approval.

For more options, use the search bar at the top of the page and adjust the filters to find the Historic Seaport vacation rental that's perfect for your needs.