The Marquesa Hotel
3.5-star hotel with two outdoor pools and fine dining.
Located right on Fleming Street and walking distance from anywhere in Key West, this charming renovated nineteenth century home-turned-hotel looks fit for a postcard. Elegant rooms feature marble baths, are decorated in light pastel colors, and sport antique furnishings. Pools are tucked in a private, quiet central courtyard where lush greenery exudes a tranquil retreat far from the noise of the daily routine. The quiet atmosphere is in part due to the guests — no children under 14 years of age are welcome and no pets are allowed. However, the hotel offers complimentary parking (making it convenient for those driving to the Keys) and a much-talked-about restaurant — Café Marquesa — is located in the property (just slip out of those sandals and into something fancy).
3.5-star hotel with two outdoor pools and fine dining.
Step out of the touristy hub of Key West and stay at Sunset Key Cottages on the secluded 27-acre island of Sunset Key. Pastel-colored wood porches lined with rocking chairs offer beachfront views while tiki huts line the perimeters of the island, which is surrounded by lush tropical vegetation. Each cottage features 1-4 rooms with garden or oceanfront views, an open living and dining area and a kitchen with stove-top if you want to cook and pre-stocked food and beverage items for purchase. The wraparound veranda with Adirondack chairs and tables make a charming breakfast spot.
4-star beachfront resort with outdoor pool.
Take in the scenic ocean views from the comfort of a hammock. The Southernmost House boasts a sprawling backyard lined with palm trees, a pool and loungers perched along the sandy beach for a front-row view of the sunset. The boutique hotel is located on the quieter end of Duval Street and is set in an enchanting three-story Victorian Home with bay windows and charming verandas. A continental breakfast can be enjoyed from the terrace dining area. Only adults 18 years and over are welcome.
Historic Beachfront Boutique Hotel in Key West, Florida.
Constructed in 1892 by the Cuban cigar manufacturer Teodoro Perez, this historic house-turned-hotel maintains a true old-world style while offering entertainment and dining. La Te Da has an in-house restaurant serving delicious seafood with a dining area by the pool, a bar, and a jazzy cabaret with show tickets costing only $26. And check out Deluxe Room 27, a 220-square-foot room that’s extra spacious and features a natural pine wall style and a private porch with a view of the pool.
Historic hotel with dining, bar and cabaret.
With its swanky modern décor and waterfall outdoor pool, the Saint Hotel is a stylish place to stay for those looking for a rest after a night of festivities. Rooms are decorated in a cool white and royal blue color palette with a private balcony overlooking the pool area. The Essera Spa offers massages in-room and a convenient Pilar Bar carries beer, wine, and champagne cocktails to unwind and relax. The property has a no-pets policy and is non-smoking, although there is a designated smoking area for a fee. Restaurants and bars are just a short walk away.
Romantic hotel with outdoor pool and spa.
Smack dab in the heart of Old Town, Key West, and across the street from the Ernest Hemingway Home and Museum, the Lighthouse Court Hotel is walking distance from all the major squares and shopping streets. The typical Key West architecture boasts open porches, French doors and a stunning courtyard with a large pool. Sip a few cocktails from the air-conditioned Mojito Bar & Café, or cozy up to a bench with a book and sit underneath the palm trees. Bedrooms are non-smoking and feature a soothing olive green and white color palette with all-new furnishings and modern amenities like Wi-Fi and a flat screen television. Free continental breakfast is included with all stays! Parking is provided for $10 USD/day.
Stylish modern Key West Boutique Hotel by Duval.
Previously the home of the Key West painter Robert Eugene Otto, the Artist House is one of the few historic buildings left on the island. Its Colonial Queen Ann style architecture boasts elegant verandas and columns, rocking chairs, and a pool. If you’re looking for a little intrigue, book the Turret Suite. Featured on the Discovery Channel’s “Would You Believe It!” program, the famed room is haunted by the ghost of Robert Otto’s wife who is seen meandering down the staircase in a wedding gown. Ghost or no ghost, the room is beautiful, with wood floors, sitting area, a queen bed, and even a sofa bed on the first floor. French doors open to a second-floor porch with wicker chairs for a relaxing sit and a staircase that leads to another room with a queen bed. The hotel is a stop at many of Key West’s historic tours. Children over the age of 5 are welcome. Veterans are offered 10% discount on bookings.
Boutique Bed & Breakfast Hotel
Explore Key West on foot or bicycle as this hotel is half a block away from Duval Street’s restaurants, art galleries, and nightlife. The adults-only (21 and up) property features continental breakfast and a heated saltwater swimming pool, all set in a tropical garden area. Each of the thirteen bedrooms are equipped with pillow-top mattress and modern amenities like a flat screen T.V. and internet access. The Driftwood room features a unique Jack and Jill-style bedroom with a twin bed on the second floor and double bed on ground floor, accommodating up to three guests. The interior of the Victorian house is furnished with antique arm chairs and a stand up piano that both exude charm from a bygone era.
Adults only, historic and charming bed and breakfast near Duval Street.
Covered in Hawaiian and Japanese orchids, palm trees and other tropical plants, the Gardens Hotel is a relaxing oasis to spend a tranquil holiday. Choose between booking a room in the main house or at the adjacent cottages with a pool and surrounding gardens. All cottages are pet friendly. Each is unique with Bahamas plantation-style furnishings. The Eyebrow cottage features a marble bath with Jacuzzi, making it the ideal honeymoon stay. Guests must be at least 16 years of age.
4-star bed & breakfast with two outdoor pools near Hemingway Home and Museum.
Enjoy a cozy stay at the quaint Olivia by Duval. The boutique hotel with 11 rooms features a narrow backyard deck with a pool, loungers, and a tiki hut enclosed in a wooden fence for privacy. Bedrooms vary, with some featuring elegant French doors that open up to a veranda with a view of the pool and others containing a kitchenette with a convenient stove and microwave.
Charming pink conch guesthouse by Key West Hospitality Inn on Olivia Street.