Love Island: Romantic adventures this February in Key West

Here’s how couples can fall in love all over again this February in Key West.

Sail into the sunset

Nothing says romance like watching the sun dip into the Gulf from the deck of a sailboat. Set sail with your sweetheart on a sunset cruise, where champagne, live music, and that famously fiery Key West sky create pure magic. Looking for something extra special? Look to Historic Key West Vacation Rentals Concierge Services, our team of local experts who can help you plan and book something truly special. Whether you’re seeking excursions, charters, tours, looking for bike rides, walks, day trips, or a complete personalized vacation itinerary, our concierge team’s got you covered.

Dine under the stars

From oceanfront tables to private garden patios, Key West offers secret, private niches just made for two. Book for this Valentine’s Day, or make any day this February a time to celebrate.
●       Latitudes on Sunset Key is a must for fine dining by the water. You’ll take a romantic private ferry ride across the harbor and experience one of the best restaurants in the Keys. Offering fresh local seafood and a thoughtful wine list, you’ll enjoy fine dining and exceptional ambience and service.
●       Recommended by both locals and visitors who book year after year, Antonia’s offers an intimate dining experience and fabulous Italian fare on world-famous Duval Street. Think: a Valentine’s dinner of handmade pasta, fresh local fish, chops and steaks and a selection from the restaurant’s Wine Spectator award-winning wine list.
●       At once elegant and casual, try Louie’s Backyard, where every table faces the sea and the cocktails are as refreshing as the breeze. Enjoy an impressive wine list, as well as local craft beer and hand-crafted cocktails. Here you’ll find a selection of local classics, and your meal with feel like a little getaway in itself.

Take a romantic stroll through Old Town

Walk hand-in-hand through the fabulous pastel streets of Key West’s historic Old Town. Pop into local galleries, linger over coffee at Cuban Coffee Queen, and share a slice of Key lime pie at Blue Heaven, where chickens wander the courtyard and a funky, upbeat ambience rules.

Adventure together

Couples who play together, stay together, and your next adventure is only a bike ride away. Take a spin to the Southernmost Point, rent kayaks and explore the island’s lush mangroves, or visit the Key West Butterfly & Nature Conservatory, an enchanting and soothing spot, where hundreds of butterflies and exotic birds fly free. Don’t forget to enlist the advice of our Historic Key West Vacation Rentals Concierge Services team, who can arrange special excursions and secure reservations.

Find your Zen, island-style

Balance the excitement of your Key West holiday with a healthy dose of serenity. Join a beachfront yoga class at Higgs Beach, book a couples massage, or simply lounge by your private pool at one of our fabulously romantic vacation homes.

Stay where the romance lives

We offer accommodations that provide the perfect setting for your couple’s retreat, from cozy, Conch-style cottages to luxurious homes built for two. Each of the carefully curated homes in our portfolio is just steps from the island’s best attractions, with an eye to privacy and tranquility for quiet moments together. Start planning your romantic February getaway today! Because in Key West, love isn’t just in the air, it’s in the ocean breeze, the art, the sunsets, and every memory you’ll make together. New to our portfolio are three restored cigar maker cottages, offering guests a unique opportunity to experience a slice of Key West history firsthand. Lounge on sunny porches, breathe deep in lush gardens, and enjoy timeless architecture along what the locals call Hurricane Alley, the original lane that ran past the homes of cigar factory workers in the late 1800s. Each cottage is beautifully and lovingly restored to preserve the character of the original homes, while including modern amenities, such as renovated kitchens, private outdoor spaces, and luxurious finishes.
●       Flamingo Cottage: A 2BR, 1BA adults-only home featuring traditional Dade County pine walls, vaulted ceilings, a loft sleeping space, French doors that lead to the island sunshine, and a kitchenette suited to laid-back mornings.
●       Gardenia Cottage: Like Flamingo Cottage, this 2BR, 1BA, adults-only cottage was originally built for artisan cigar workers. It features hardwood floors, a sunny living room with a skylight, loft sleeping above, and a king bedroom leading to a private brick patio.
●       Hibiscus Cottage: This 2BR, 2BA Conch-style cottage is steeped in local history. Secluded, yet situated close to many of Key West’s most popular attractions, this exclusive deluxe cottage offers a large shared pool.

When you stay in one of these homes

When you stay in one of these homes, you’re not just close to Old Town’s galleries, restaurants, and sunsets, you’re living inside a story that began more than a century ago. You’ll be a part of the romance of Key West’s rich history. All this, and more, is waiting for you in fantastic Key West!