The Best Boutique Hotels in the Florida Keys

Stay at a charming boutique hotel in the Florida Keys for that perfect laid-back vacation
Stay at a charming boutique hotel in the Florida Keys for that perfect laid-back vacation | Courtesy of the Southernmost House Hotel / Expedia.com
Photo of Karina Castrillo
30 October 2020

Whether you’re planning a romantic honeymoon vacation or a boozy break with friends, the Florida Keys are dotted with charming boutique hotels that offer a laid-back atmosphere for that perfect holiday. Here’s a list of the best hotels on our radar now.

Sunset Key Cottages

Boutique Hotel, Resort, Cottages
Map View
Sunset Key Cottages, 245 Front St, Key West
Courtesy of Sunset Key Cottages

Step out of the touristy hub of Key West and stay at Sunset Key Cottages on the secluded 27-acre (11ha) 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 one to four rooms with garden or oceanfront views, an open living and dining area, a kitchen with a stove-top if you want to cook, and pre-stocked food and beverage items for purchase. The wraparound veranda with Adirondack chairs and tables makes for a charming breakfast spot.

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The Southernmost House

Boutique Hotel, Bed and Breakfast
Map View
The Southernmost House, Key West
Courtesy of the Southernmost House / Expedia.com

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.

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The Saint Hotel

Boutique Hotel, Hotel
Map View
The Saint Hotel Key West, Autograph Collection, Key West
Courtesy of the Saint Hotel Key West

With its swanky modern decor and waterfall outdoor pool, the Saint Hotel is a stylish place to stay for those looking for a rest after a night of festivities. Each room is decorated in a cool white and royal blue color palette with a private balcony overlooking the pool area. The Essera Spa offers in-room massages, and the convenient Burgundy Bar carries beer, wine and champagne cocktails when you want 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.

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Lighthouse Hotel

Boutique Hotel, Homestay, Hotel
Map View
Kimpton Lighthouse Hotel, Key West
Courtesy of Lighthouse Hotel / Expedia.com

Smack dab in the heart of Old Town, and across the street from the Ernest Hemingway Home and Museum, the Lighthouse 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 Isabel’s Bar, 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 wifi and a flatscreen television. Limited parking is available for $20 (£15) per day.

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Marrero’s Guest Mansion

Boutique Hotel, Bed and Breakfast
Map View
Marrero's Guest Mansion, Key West
Courtesy of Marrero's Guest Mansion / Expedia.com

Explore Key West on foot or bicycle, as this hotel is half a block away from Duval Street’s restaurants, art galleries and nightlife. This 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 13 bedrooms is equipped with a pillow-top mattress and modern amenities like a flatscreen TV 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 armchairs and a stand-up piano that exude charm from a bygone era.

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The Gardens Hotel

Boutique Hotel, Bed and Breakfast
Map View
The Gardens Hotel, Key West
Courtesy of the Gardens Hotel / Expedia.com

Covered in Hawaiian and Japanese orchids, palm trees and other tropical plants, the Gardens Hotel is a relaxing oasis in which 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-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.

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  • Olivia by Duval

    Guesthouse
    Map View

    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.

    La Te Da

    Boutique Hotel, Hotel
    Map View
    La Te Da, Key West
    Courtesy of La Te Da Hotel

    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 $33 (£25). And check out Deluxe Room 27, a 220-square-foot (20sqm) room that’s extra spacious and features a natural pine wall and a private porch with a view of the pool.

    The Artist House

    Boutique Hotel, Bed and Breakfast
    Map View

    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 Anne-style architecture boasts elegant verandas and columns, complemented by 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 purportedly haunted by the ghost of Robert Otto’s wife who can be seen meandering down the staircase in a wedding gown. Ghost or no ghost, the room is beautiful, with wood floors, a 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 five are welcome. All active military personnel are offered a 10% discount on bookings.

    About this place:

    Historic, Beach, Boutique, Relaxed, Romantic, Hidden Gem

    The Marquesa Hotel

    Boutique Hotel, Hotel
    Map View
    The Marquesa Hotel, Key West
    Courtesy of the Marquesa Hotel / Expedia.com

    Located right on Fleming Street and within walking distance of anywhere in Key West, this charming renovated 19th-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 daily life. 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 the much-talked-about restaurant – Café Marquesa – is located on the property (just slip out of those sandals and into something fancy).

    These recommendations were updated on October 30, 2020 to keep your travel plans fresh.

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