A long-term stay makes an ideal couples retreat

Live Like Locals Through Historic Key West Vacation Rentals. 

This February, imagine waking up to the soft rustle of palm trees, savoring coffee on your private veranda and embracing island life as if it were your own. Couples seeking a deeper connection to each other should look no further than an extended stay in Key West. At Historic Key West Vacation Rentals, we pride ourselves in offering a unique experience with our portfolio of gorgeous restored historic homes.

With an extended stay, consider becoming digital nomads — bring along the laptops and work remotely for a month or longer while trying out an immersive experience in paradise. Retirees chasing a change of scenery, or partners looking to enrich their relationship can experience the local lifestyle and become a part of the community by spending a month or more in this fabulous tropical paradise. Why not turn Valentine’s Day into the adventure of a lifetime. Historic Key West Vacation Rentals is standing by to help you realize your Valentine’s Day dreams.

Choose a long-term stay

Here are just a few reasons to consider an extended Valentine’s Day stay in Key West with Historic Key West Vacation Rentals:

A laid-back lifestyle

Key West’s easygoing “come as you are” attitude makes it an inviting escape from a crazy world. Here, time seems to slow down, offering a chance to savor simple pleasures — a romantic sunset stroll, gentle ocean breezes, and the freedom to focus on each other.

A remote worker’s dream

Go ahead and extend your long Valentine’s Day weekend to a month-long adventure by becoming a digital nomad. For those working remotely, Key West provides the ultimate office upgrade. Picture virtual meetings on a sunlit porch or a brainstorm session on the beach. All our rentals offer reliable Wi-Fi, so you can seamlessly balance work and play.

Activities for every couple

From snorkeling in crystal-clear waters to touring art galleries, museums and historic neighborhoods, Key West offers endless opportunities for couples to bond. With an extended stay, you’ll have the time to try new experiences together. Take a sailing lesson or a cooking class that features local flavors. You’ll be creating memories you’ll treasure for a lifetime.

A supportive community

Staying for 30 days or more in a Historic Key West Vacation Rental property allows you to immerse yourself in a tight-knit community. Get to know friendly locals, become a regular at the local farmers markets, and participate in events that make you feel like part of the island family.

Why stay with us?

Long-term stays deserve accommodations that feel like home. When you stay for a month or more, you can unpack, break out your flip-flops and take a deep breath. At Historic Key West Vacation Rentals, our lovingly restored and curated properties offer the ultimate balance of comfort, charm and convenience for couples settling in for an extended time.

Fully equipped

Check out our list of long-term rental properties that provide everything you need to make yourselves feel perfectly at home. From gourmet kitchens to comfortable indoor and outdoor living spaces, you’ll find the ideal base for your island life.

Privacy and serenity

Our charming historic homes are designed to offer peace and tranquility. Many include private pools, lush tropical gardens, and outdoor spaces where you can unwind and reconnect with each other.

A balance of work and play

Our properties feature work-friendly amenities, including dedicated office spaces and high-speed internet, so you can keep up with work, if necessary, while enjoying your surroundings. When the workday ends, the island awaits you, just steps outside your door.

Proximity to adventure

Situated in some of the most desirable areas of Key West, our beautiful homes allow easy access to everything the island has to offer. Walk to the beach, bike through Old Town or enjoy fresh seafood at local restaurants — you’ll enjoy convenient locations to access all the excitement of Key West.

Enrich your relationship

Spending a month or more together in Key West offers a unique opportunity to focus on your relationship. Cook meals together with fresh local ingredients, create new traditions like morning walks along the beach followed by coffee at your favorite café, or simply enjoy relaxing in each other’s company without distractions. The island’s romantic ambiance naturally encourages a deeper connection.

Plan your extended stay today

A long-term stay in Key West isn’t just a vacation — it’s a chance to live a dream life, even if just for a while. You can settle in and forget the stress of travel because you’ll be living the local lifestyle. Strike a balance of work-life harmony, local charm and romantic moments, and you’ll leave with stronger bonds and unforgettable memories. Ready to embrace the island lifestyle this February? Explore our collection of long-term rental properties at Historic Key West Vacation Rentals and begin planning your stay in paradise today. Here are a few selections from our portfolio to inspire your extended stay:

• Blue Haven: Just beyond the bougainvillea-adorned front gate, this spectacular 4BR, 3BA home away from home beckons with an allure of privacy and luxury. A large living room with Italian leather sofa looks out through French doors to the tropical paradise out back, and an updated kitchen features granite countertops, gleaming stainless steel appliances and an adjacent wet bar. You’ll find lots of space to relax outside, such as a pool with deluxe water features, an outdoor shower, sunshades, loungers, dining table and fire pit. Here at Blue Haven, you’re within walking or biking distance to wonderful Higgs Beach and many of the island’s most important landmarks and attractions.

• Copa Cabana: You won’t believe your luck when you check into fabulous Copa Cabana for an extended vacation stay. This 2BR, 2BA home’s location in Bahama Village, south of Truman Ave., features historic cottages and peaceful tree-lined streets. Your welcome begins with a white picket fence and homey rocking chair on the front porch of this 1923 shotgun home, a traditional architectural style in Key West. You’ll find a built-in work station just off the open concept living room, and ceiling fans and hardwood floors add to the cool ambience. Celebrate happy hour in your private jetted cocktail pool, and feel free to cook up the catch of the day on the gas grill.

• Sunny Daze Cottage: Settle in for a month or more in this newly constructed 2BR, 2BA home, featuring a beautiful open concept family room flooded with natural light and upscale decor. Sunny Daze Cottage boasts a pristine design aesthetic with a soothing color palette. You’ll find a spacious king bedroom with an ensuite bath and a beautiful modern kitchen. Out back, you’ll relax on a sectional sofa and dine under the stars surrounded by a lush tropical landscape. From this quiet residential neighborhood, you’re just steps away from vibrant Old Town Key West.