We love the Florida Keys for so many reasons: the sun, the sand, the seafood, the sunsets, the nightlife... And fortunately for most East Coasters, the Keys are easy enough to reach that a weekend getaway to the beach (that doesn't feel rushed) is totally doable. Not to say that you'll want to leave, but at least your travel time with be short enough that you'll have plenty of time to chow down on key lime pie and sip on margaritas even during a quick trip. On our recent jaunt to the Keys, we visited a slew of adorable properties and confirmed what we've believed to be true for some time -- the Florida Keys are home to some of the cutest boutique hotels EVER. From a two-room hotel on a quiet street to a luxe adults-only property on its own private island, here are our ten favorite boutique hotels in the Florida Keys, NEW on Oyster.com!
Okay, so it’s not that small. But boat rides, fishing charters, and dive trips are just some of the perks available at Casa Morada! Inspired by a laidback Caribbean lifestyle, this upscale 16-suite boutique hotel is perfect for couples looking for a romantic getaway, whether for a honeymoon or just because. Situated right next to the ocean in the middle of the Florida Keys on Islamorada, the hotel provides a peaceful and serene atmosphere with hanging hammocks and lots of fun and free activities like yoga classes, kayaking, and bicycle rentals. Compared to nearby hotels, this property offers great value with spacious and upscale rooms with water views.
Orchid Key Inn is a 24-room, upper-middle range boutique located on Duval Street in the heart of Key West’s tourist area and within walking distance of lively bars, outdoor cafes, and unique shops. Though it doesn’t look like much from the outside, the interior of the hotel is renovated, elegant, and stylish with an orchid design motif found throughout the property and chic rooms. There is a big pool with lush landscaping and one free drink during happy hour at the poolside bar, but no on-site restaurants serve lunch or dinner. Rates are competitive given the hotel’s central location and modern style.
Santa Maria Suites, with 35 spacious suites with full-size kitchens, is an upscale, four-pearl property in the southernmost part of historic Key West. Guests get lots of freebies here — such as bottled water, wine hour with snacks, smoothies, and ice-cream bars — but a mandatory resort fee is added to the bill. Santa Maria Suites is about a block from the beach and walking distance to the south end of Duval Street. This property, with its condo-style suites, can offer good value to families, couples, and groups of friends traveling together.
Reachable only by boat or seaplane, Little Palm Island Resort & Spa is located on a private island where wild key deer roam. It includes 30 luxurious suites, many with private oceanfront verandas. A favorite getaway for celebrities, it provides a secluded place to unplug from the world (use of technology is discouraged) and experience a romantic vacation in a lush, tropical environment.
With only two rooms, the Atlantis House is an exclusive and private inn owned and maintained by a couple named Steve and Kayla. Unlike traditional hotels, the owners offer unique and personal services — Steve is a licensed boat captain who takes guests on fishing excursions and Kayla is a licensed massage therapist. Both are excellent cooks. The two rooms are private and decorated in a bold and vibrant decor with wares from world travels. A long walk from the heart of Key West’s bar district, Atlantis House is more suited for a couple looking for a weekend getaway from the hustle and bustle of everyday life.
The Mermaid and The Alligator is a nine-room upscale bed and breakfast housed inside a historic Victorian estate. The owners have taken great care to renovate the home with bold and vibrant decor and updated furnishings. Located on Truman Street, three blocks from popular Duval Street, the home is a quiet and peaceful area that is steps from the heart of the entertainment district. There is a lush interior garden with hammock, lounge chairs, and plunge pool, but there are no on-site restaurants for lunch and dinner and the cancellation policy is strict.
The Almond Tree Inn is an upper-middle-range boutique, offering 22 stylish rooms decorated in yellow, green, and white tropical decor. It’s a great value compared to other nearby hotels, providing both free breakfast and a free happy hour. Property features include a serene pool courtyard with waterfalls and lush landscaping, and the location is in the heart of Old Town Key West, within walking distance of Duval Street.
Located inside a historic, late 19th-century house, the 10 rooms at the Key West Bed and Breakfast exude intimate luxury. Vibrant art and local flare converge in this Victorian-style property, which has a wide, Southern-style front porch and beautiful architecture. This charming property is a great fit for couples looking for a romantic getaway but who also want to be close to all the action on Duval Street and the sunset celebrations on Mallory Square. Rooms on the second floor share bathrooms, while rooms on the first and third floors are more spacious, and some have private sundecks.
Alexander’s Guesthouse is an intimate, 17-room bed and breakfast designed especially for the LGBT community and supporters. It’s a historic property that’s been completely renovated — including the guest rooms, living room style lobby, pool area, and kitchen. The only meal served on property is the free breakfast, but there are tons of dining choices located within walking distance on lively Duval Street. Rates are comparable to competitors and rooms tend to book fast during the busy seasons, with a strict cancellation policy and minimum stay requirement at times.
The 37-room Key Lime Inn is an intimate boutique with a heated outdoor pool and sunny terrace. Though located just blocks from popular shopping, dining, and nightlife attractions on Duval Street, this hotel manages to retain a peaceful feel. Rooms are set in cute clusters of buildings, some dating back to the 19th century. There is a free, basic continental breakfast served by the pool but there are no restaurants or bars that serve lunch or dinner and Wi-Fi can be inconsistent.
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