The Best Boutique Hotels to Book 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
Karina Castrillo

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, all bookable with Culture Trip.

1. Simonton Court Historic Inn & Guesthouse, for unique lodgings


Swimming pool and outdoor area at the Simonton Court Historic Inn and Guesthouse in the Florida Keys
Courtesy of Simonton Court Historic Inn and Guesthouse / Expedia

This adults-only B&B offers stylish, historic stays in restored Victorian surroundings. Choose from rooms in the 90s Bahamian-style mansion; the poolside inn, a former cigar factory; cottages formerly home to factory workers; Manor House, once a shotgun house; or the two-story stucco Townhouse with courtyard-facing suites. All guests can dip into the four 24-hour pools, chill in the gardens and tuck into complimentary continental breakfast. Concierges can arrange activities from jet ski tours to dolphin watching.

2. The Cabana Inn, for a relaxed haven


A swimming pool and outdoor area at The Cabana Inn in the Florida Keys
Courtesy of The Cabana Inn / Expedia

This adults-only hotel in the Florida Keys is one block from Duval Street but remains a relaxing, tree-surrounded haven. Rest in your room or suite in the historic estate and cottages: bright and modern decor with classic wood and sky-blue accents, plus handy coffee-makers, microwaves and mini-fridges. Find peace in the sunny, bed-strewn courtyard with its lagoon-style pool and jacuzzi, and take advantage of the fee-inclusive amenities: continental breakfast, 24-hour Starbucks coffee and wine and cheese happy hour.

3. The Mermaid & Alligator, for a romantic stay


A bedroom with green and yellow decor at The Mermaid and Alligator in the Florida Keys
Courtesy of The Mermaid and Alligator / Expedia

This adults-only, three-blocks-from-Duval-Street B&B is romantic and intimate with just nine rooms. Check into the Victorian mansion featuring Dade County Pine floors – original windows and spa-style bathtubs in some – or the in-garden 1880s cottage rooms with eclectic, boutique-style furnishings. The friendly staff will serve all-inclusive poolside breakfasts: local coffee, continental options and a daily-changing hot dish from avocado toast to Belgian waffles. Relax in the lush garden’s rocking chairs and indulge in massages in the plant-surrounded cabana.

4. Oceans Edge Key West Resort, Hotel & Marina, for endless choice


Oceans Edge Resort pool area with plush lounge chairs, blue umbrellas and row of palm trees in Key West, Florida
Courtesy of Oceans Edge Resort and Marina / Expedia

Check into an ocean-view, balcony-clad room or suite to enjoy this 20-acre (8ha) resort with activities, from poolside film screenings to sunset cruises or eco boat experiences (with scientists and live animals) from the full-service marina. Visit the Old Town with complimentary bike rental and shuttles; finish days at the resort restaurant serving marina-caught seafood or your own catch and time it right for live music. You’re spoiled with six swimming pools, poolside bars and a waterfront dog park for your welcomed furry friend.

5. Little Palm Island Resort & Spa, for switching off

Resort, Spa Hotel

A birds-eye view of the green island where the Little Palm Island Resort and Spa is located
Courtesy of Little Palm Island Resort and Spa
Switch off at this adults-only, no-phones getaway – America’s only private island resort, reachable by seaplane or boat. Sunbathe at the four-acre (1.6ha) beach or ocean-view pool and enjoy complimentary kayaks, boats or paddleboards. Into wellness? Book a SUP yoga session or the spa’s sustainably-sourced seaweed body rituals. Sample the view-clad restaurant’s dishes made with island-sourced seafood and spices. You’ll stay in a thatched-roof, palm-surrounded, ocean-view bungalow with luxury living spaces. Choose a private deck and outdoor tub-included room for ultra-luxury.

6. The Southernmost House, for a boutique feel

Boutique Hotel, Bed and Breakfast

A swimming pool and sun loungers at The Southernmost House in Key West
Courtesy of the Southernmost House /

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.

7. The Saint Hotel, for chic modernity

Boutique Hotel, Hotel

Outside view of The Saint Hotel Key West with a red carpet and white decor
Courtesy of the Saint Hotel Key West

With its swanky modern decor and outdoor waterfall 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.

8. Lighthouse Hotel, for a beautiful courtyard

Boutique Hotel, Homestay, Hotel

Outdoor deck area with sofas and loungers at the Kimpton Lighthouse Hotel in Key West
Courtesy of Lighthouse Hotel / Expedia

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.

9. Marrero’s Guest Mansion, for thoughtful amenities

Boutique Hotel, Bed and Breakfast

Outside view of the Marreros Guest Mansion in Key West, Florida
Courtesy of Marrero's Guest Mansion / Expedia

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 a continental breakfast and a heated saltwater swimming pool, all set in a tropical garden area. Each of the 12 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 a double bed on the 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.

10. The Gardens Hotel, for leafy tranquility

Boutique Hotel, Bed and Breakfast

Outdoor pool area surrounded by lush foliage at the Gardens Hotel, Key West
Courtesy of the Gardens Hotel / Expedia

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 adjacent cottages with a pool and surrounding gardens. All cottages are pet-friendly. Each has Bahamas-style furnishings. The Eyebrow cottage features a marble bath with a jacuzzi, making it the ideal honeymoon stay. Guests must be at least 16 years of age.

Kim Gregory contributed additional reporting to this article.

To have everything at your fingertips, check out the top hotels or best resorts in Key West, Florida. Alternatively, check out the best beach hotels in the Florida Keys, bookable with Culture Trip.

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