Your Key West Vacation Starts Here

Dreaming of a sun-soaked getaway where you can experience the best of island life? Look no further than Key West, a picturesque island that offers everything from stunning sunsets to rich history and exciting activities. Nestled at the southernmost point of the United States, Key West promises a vacation experience unlike any other.

At Historic Key West Vacation Rentals, we provide premium accommodations that make you feel right at home while enjoying the charm and beauty of this tropical paradise. Whether you’re visiting for a romantic retreat, a family vacation, or a group getaway, we have the perfect home for you.

Stay in the Heart of Key West’s Historic District

The best way to truly experience Key West is by staying in Key West's Historic District, also known as Old Town. This area, located on the western side of the island, boasts charming, pastel-colored homes and quaint streets lined with lush tropical foliage.

At Historic Key West Vacation Rentals, we offer a carefully curated selection of vacation homes, cottages, and condos, all situated in this iconic neighborhood. Imagine staying in a beautifully restored Conch house, complete with modern amenities while being just steps away from Key West's famous attractions like Duval Street, the Ernest Hemingway Home, and the Southernmost Point.

Our vacation rentals range from cozy one-bedroom cottages to expansive six-bedroom homes, ensuring that no matter the size of your group, we have the ideal accommodation for your Key West vacation. With open and spacious interiors, chef’s kitchens, and private outdoor spaces, our homes provide the perfect blend of comfort and luxury. For those working remotely, our properties are equipped with high-speed internet and quiet workspaces, so you can extend your vacation without missing a beat.

Key West Vacation: Where Local Life and Island Fun Meet

What sets Key West apart from other vacation destinations in the Florida keys is its unique blend of laid-back island living and vibrant local culture. When you stay with Historic Key West Vacation Rentals, you’re not just visiting—you’re living like a local.

Our vacation homes are located in walkable neighborhoods where you can easily explore the island’s many attractions on foot or by bike. Stroll down the iconic streets of Old Town, lined with colorful homes, quaint shops, and lively cafes, or head to the water for a day of adventure. Key West is known for its world-class fishing, snorkeling, and diving spots, offering endless opportunities to explore the vibrant coral reefs and marine life that surround the island.

And when the sun goes down, Key West comes alive with a vibrant nightlife scene. From the nightly sunset celebration at Mallory Square to the lively bars and restaurants on Duval Street, there’s always something happening in this island paradise. Whether you’re looking for a quiet evening under the stars or a night of live music and dancing, Key West offers something for everyone.

Extended Stays and Flexible Options

At Historic Key West Vacation Rentals, we understand that every vacation is unique, which is why we offer flexible options to suit your needs. Whether you’re planning a short getaway or an extended stay, our collection includes nightly, weekly, and monthly rental options.

During most of the year, our minimum stay requirements range from three to five nights, giving you plenty of flexibility to plan your perfect Key West vacation. However, for special events like New Year's, Fantasy Fest , or popular holiday weekends, a seven-night minimum may apply.

Planning an extended stay? Our monthly rentals are the perfect option for those looking to fully immerse themselves in the Key West lifestyle. Stay for 28 nights or more and enjoy the island at your own pace. With our spacious homes and comfortable amenities, you’ll feel like a true local by the end of your stay.

For more information on long-term stays, visit our Monthly Rentals Page.

Traveling with Pets? No Problem!

Key West is one of the most pet-friendly vacation spots in the country, making it an ideal destination if you’re traveling with your four-legged friend. With dog-friendly beaches, parks, and even restaurants, your pet will feel just as welcome on the island as you do.

At Historic Key West Vacation Rentals, we offer a selection of pet-friendly homes that are perfect for you and your pup. Simply let us know when booking, and we’ll ensure your furry companion has everything they need for a comfortable stay.

Before booking, please review our pet policies, as we allow one dog under 25 pounds per rental. You can learn more by visiting our Pet-Friendly Rentals Page.

Cool Off in Your Private Pool

One of the best parts of a Key West vacation is enjoying the warm tropical weather, and what better way to do that than by lounging by your own private pool? Many of our vacation rentals include private pools, where you can cool off after a day of exploring the island or simply relax with a good book in the sun.

Whether you're floating in the pool or dining al fresco by the water, the privacy and convenience of your own pool add a touch of luxury to your Key West vacation.

For those visiting during the cooler months, select rentals offer seasonally heated pools for an additional fee, ensuring you can enjoy the water year-round. If a private pool isn’t a necessity, we also offer rentals with access to community pools, providing a perfect blend of socializing and relaxation. Explore our collection of Vacation Rentals with Private Pools for more options.

Group Vacations and Special Events

Planning a wedding, family reunion, or group getaway? Our collection of vacation rentals includes properties that are ideal for group travel. Some of our homes are located within private compounds, featuring shared amenities like pools and outdoor decks, perfect for gathering together. Each property within the compound can be rented individually or as a whole, allowing you to enjoy your privacy while still being close to your group.

Our group-friendly rentals are also perfect for special events. If you’re hosting a wedding in Key West, our properties provide comfortable and convenient accommodations for your guests. With plenty of space, luxurious amenities, and a location in the heart of Old Town, your wedding party will be able to relax and enjoy the island’s beauty.

Discover the Best of Key West

Key West is a destination that offers something for everyone, from history buffs and foodies to adventure seekers and beach lovers. During your stay, make sure to explore some of the island’s top attractions:

• Mallory Square: Don’t miss the nightly sunset celebration, where locals and visitors gather to watch the sun dip below the horizon while enjoying live music, street performances, and food vendors.
• Ernest Hemingway Home and Museum: Step back in time and visit the famous author’s Key West residence, complete with lush gardens and six-toed cats.
• Duval Street: This lively street is the heart of Key West’s nightlife and dining scene. Enjoy a meal at one of the many restaurants or dance the night away at a local bar.
• Fort Zachary Taylor State Park: Known for its beautiful beaches and historic fort, this park is a must-visit for those looking to soak up some sun and explore Key West’s history.

For more ideas, visit our Events in Key West page.

Plan Your Key West Vacation Today

There’s no better time to plan your dream Key West vacation. Whether you’re seeking a quiet retreat or an adventure-filled getaway, Historic Key West Vacation Rentals has the perfect home for you. Our experienced and friendly local team is here to help you every step of the way, from choosing the right rental to recommending the best activities and restaurants on the island.

Call us today at 305-296-1010, Option 1, or email us at bookings@historickw.com to start planning your unforgettable Key West vacation.