Your Guide to Key West Long-Term Rentals

Live the Island Dream with a Long Term Rental in Key West

Imagine starting your day with the sound of swaying palm trees and ending it with a stunning sunset over the ocean. Key West long-term rentals offer more than just a getaway—they provide the opportunity to immerse yourself in island life. Whether you're a remote worker, retiree, or couple looking for an extended retreat, long-term rentals are the perfect way to embrace the laid-back charm of Key West.

At Historic Key West Vacation Rentals, we specialize in providing unique accommodations that combine historic charm with modern comfort. Here's everything you need to know to plan your ideal long-term stay.

Why Choose Long-Term Rentals in Key West?

Key West's vibrant culture and tropical beauty make it an unmatched destination for long-term stays. Here’s why staying longer is better:

Escape the Hustle and Bustle

Trade the chaos of daily life for a relaxed island lifestyle. Key West’s "come as you are" attitude encourages you to slow down and savor the moment, whether it’s a romantic sunset stroll or a bike ride through Old Town.

A Remote Worker's Paradise

Key West isn’t just for vacations—it’s perfect for digital nomads. Reliable high-speed internet, sunny porches for virtual meetings, and scenic surroundings offer the ultimate work-life balance.

Be Part of a Community

With a 30-day or longer stay, you’ll experience life as a local. From attending farmers markets to participating in community events, you’ll feel like a true Key Wester.

Top Activities to Enjoy During Your Extended Stay

An extended stay means more time to experience Key West’s best attractions and activities.

Explore Historic Old Town

Stroll through picturesque streets lined with charming homes and lush gardens. Don’t miss the Ernest Hemingway Home & Museum and other historic sites.

Dive into Adventure

From snorkeling in vibrant coral reefs to kayaking through mangroves, Key West offers endless outdoor activities. Long-term stays mean more time to try something new every week.

Indulge in Island Cuisine

Enjoy fresh seafood and Caribbean-inspired dishes at local restaurants like Blue Heaven or Louie’s Backyard. With more time, you can explore both hidden gems and iconic spots.

Why Stay with Historic Key West Vacation Rentals?

We take pride in offering long-term rentals that feel like home. Here’s what sets us apart:

Historic Charm Meets Modern Comfort

Our beautifully restored homes blend timeless Key West architecture with modern amenities. From gourmet kitchens to private pools, every detail is designed for comfort and convenience.

Fully Equipped for Extended Stays

Each property includes essentials for long-term living, such as high-speed Wi-Fi, workstations, and fully stocked kitchens. Whether you’re working or unwinding, you’ll find everything you need.

Prime Locations

Our rentals are ideally situated near beaches, restaurants, and attractions, giving you easy access to the best of Key West.

Featured Long-Term Rentals

Blue Haven

A luxurious 4BR, 3BA home with a private pool, spacious outdoor areas, and proximity to Higgs Beach. Perfect for families or couples seeking serenity and style.

Copa Cabana

This cozy 2BR, 2BA cottage features a jetted cocktail pool, built-in workstation, and a location in historic Bahama Village.

Sunny Daze Cottage

A modern 2BR, 2BA home with an open-concept design, tropical outdoor living spaces, and easy access to Old Town.

Plan Your Key West Escape Today

A long-term stay in Key West isn’t just a vacation—it’s a chance to live the island life. From immersing yourself in the community to enjoying unmatched comfort in our rentals, you’ll leave with cherished memories and a renewed connection to what truly matters. Ready to turn your dreams into reality? Browse our collection of long-term rentals at Historic Key West Vacation Rentals and start planning your stay.