Season is gearing up for another wave of swooning partners and sunset seekers as we enter the romance tinged month of February. With an incredibly diverse offering of warm and high end accommodations, sumptuous wine bars, and sensational restaurants, here is a look at seven dreamy choices for a romantic rendezvous.

La Mer & Dewey House Luxury Ocean View

Part of the Southernmost Beach Resort, this hidden gem is described “like a bed & breakfast — but elevated.” This restored turn-of-the-century Victorian home offers exclusive concierge level amenities, a private balcony, and a daily breakfast prepared by the in-house chef. With stunning views of the sunrise and walking distance to major downtown attractions, the beautiful premises will make you fall in love with the island all over again. 

508 South Street

La Crêperie French Cafe

Sweet or savory? Start your morning at this super charming enclosed French eatery — complete with a petite shaded patio reminiscent of the charming cafes of Paris. We recommend La Red Velvet, The Famous. This crêpe is an explosion of berries coulis, chocolate ganache, strawberries, and ice cream on a galette. Pair it with a dedicated selection of bubbles, reds, and whites conveniently kept on hand. Skip the morning pillow talk and dig into a fantastic breakfast.

300 Petronia Street

Besame Mucho 

Just off of Duval Street and nestled in the heart of Bahama Village, the atmosphere of charm and old-world connections is sure to encourage a sense of escape. Cozy fashions, antique jewelry, botanical mists, and eclectic home designs all coalesce to sweep you off your feet in an absolutely surreal shopping experience. Nothing says I love you quite like a sapphire purchased in paradise. 

315 Petronia Street

Classic Harbor Line, Schooner America 2.0

Sail into the sunset this Valentine’s aboard the Schooner America 2.0. This Champagne and Aphrodisiacs Pairing Sunset Sail caters to your taste buds and thirst to catch the ever elusive flash of green as you sail off of the coast on a fun and romantic evening on the water. This intimate affair promises to create a unique ambience fitting for both first time visitors to the island and veterans of Key West’s stunning ocean views. 

202 William Street

Gardens Hotel 

This beautiful oasis of lush garden flora and easy breezy poolside vibes is a sophisticated retreat a block away from Duval. With weekly jazz, cabaret, and live entertainment coupled with the on site Divine Wine Gallery, this fantastic discovery is a gem of an experience after a day out and about. Dubbed “The Prettiest Hotel in Key West,” guests have a choice of master suites, cottages, and individual boutique rooms that comprise this green-certified compound that also boasts a heated pool, complimentary breakfast, and a bird aviary for you to explore with your significant other.

526 Angela Street


The Mermaid & The Alligator Bed & Breakfast

This winner of the 2018 Experts’ Choice Awards and 1904 Queen Anne Victorian mansion hosts lush gardens that enclose a beautiful plunge pool. Its outdoor pavilion is a wonderful space to mingle with other guests, couples, and singles while enjoying the complimentary breakfast or early evening wine. Each room is described as encapsulating its own “distinct personality” with such warm and quirky options as the Treetop Suite, Key Lime Room, and Royal Poinciana, which are perfect for the stylish couple looking for original design and decor. As an added bonus, the bed & breakfast provides several romantic “enhancements” upon request to add that unforgettable surprise to your significant other’s experience in paradise. 

729 Truman Avenue