Oyster Pearl Rating

  • Award-Winning

Point of Interest

from
    See More

    What's Your Style?

      See More

      Locations

        See More

        Amenities

          See More

          Key West Hotels

            74 Hotels Found
            1. Casa Marina Key West, A Waldorf Astoria Resort
              Key West, Florida Keys, Florida
              • Beachfront
              • Luxury
              • Resort
              • Romantic
              The 311 rooms of the Casa Marina Resort have a light, sophisticated, but still island-y feel, with neutral tones, sheer curtains, and sleek hardwood or tiled floors. The resort also offers great in-room amenities, including free Wi-Fi, flat-screen TVs, and espresso machines. Although bathrooms grand…
            2. Sunset Key Cottages
              Key West, Florida Keys, Florida
              • Beachfront
              • Boutique
              • Kid-Friendly
              • Romantic
              This 27-room resort caters to the upscale traveler with luxurious, beach-chic cottages and high-end amenities. It is located on Sunset Key, a residential island off Key West, and is affiliated to the Margaritaville Key West Resort and Marina, with which it shares some features. The hotel itself has…
            3. Southernmost Beach Resort
              Key West, Florida Keys, Florida
              • Beachfront
              • Kid-Friendly
              • Luxury
              • Romantic
              The 124-room Southernmost on the Beach is an upscale property located on the beach in southern Key West. Spacious rooms offer a host of modern comforts including Nespresso machines, and many have lovely, private balconies, some with spectacular ocean views. Highlights here include the beautiful, a a…
            4. The Reach Key West, A Waldorf Astoria Resort
              Key West, Florida Keys, Florida
              • Beachfront
              • Luxury
              • Resort
              • Romantic
              The Reach offers respite from rowdy, gaudy Key West with its brand of relaxed sophistication and its beachfront location. Its 150 rooms are what you would expect from the Waldorf Astoria crowd: spacious, modern and clean, with generic high-end furnishings and comfortable beds outfitted in crisp They…
            5. Marquesa Hotel
              Key West, Florida Keys, Florida
              • Boutique
              • Historic
              • Romantic
              Refurbished from 1884 conch houses, the Marquesa Hotel is a compound of four buildings surrounding lovely interior gardens and two pools. A narrow staircase off the lobby leads to the individually decorated rooms. Light and airy rooms feature flat-screen TVs, mini-fridges, and cozy sitting areas are…
            6. Margaritaville Key West Resort & Marina
              Key West, Florida Keys, Florida
              • Kid-Friendly
              • Luxury
              • Resort
              • Romantic
              This 178-room waterfront hotel in Old Town Key West is a real resort, with dozens of features, including boat rentals, shops, a fitness center, and a marina. However, it’s not quite up to the standards of other luxury properties, with somewhat bare contemporary rooms, cramped bathrooms, a pool a bit…
            7. Pier House Resort & Spa
              Key West, Florida Keys, Florida
              • Beachfront
              • Historic
              • Luxury
              • Romantic
              A full-service, four-pearl hotel in a town filled with B&Bs, this property differentiates itself from the competition by providing more rooms and more amenities -- including an on-site spa, pool, restaurant/bar, and beach access -- in a convenient downtown location. Rooms are simple and comfy with A…
            8. Ocean Key Resort & Spa
              Key West, Florida Keys, Florida
              • Boutique
              • Luxury
              • Resort
              • Romantic
              The 100-room Ocean Key Resort is an upscale waterfront property with an elegant atmosphere that captures the artistic whimsy of Key West. Contemporary rooms have large, comfortable beds, whirlpool tubs, and minibars, plus feature a cheerful, island-flavored design. There are two restaurants on-site…
            9. Havana Cabana at Key West
              Key West, Florida Keys, Florida
              • Kid-Friendly
              • Romantic
              Havana Cabana Key West will reopen April 2018. Havana Cabana Key West is a 106-room, upper-middle range hotel that overlooks the Gulf of Mexico and features a tropical-style pool with tiki bar in the center of the property. Popular Duval Street is not located within walking distance, but given Key a…
            10. Southernmost House
              Key West, Florida Keys, Florida
              • Adults-Only
              • Beachfront
              • Bed and Breakfast/Inn
              • Boutique
              • Historic
              • Romantic
              The Southernmost House is an adult-only property in an historic Victorian home directly on the ocean and just off popular Duval Street. This 18-room, mid-range inn feels sophisticated but laid-back, and has hosted the likes of Hemingway and Capote. Its genteel sitting porches, antique furnishings, a…
            11. Santa Maria Suites Hotel
              Key West, Florida Keys, Florida
              • Kid-Friendly
              • Value
              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 an afternoon wine hour with snacks, poolside smoothies and ice-cream bars, and bottled water and fresh at…
            12. Hyatt Centric Key West Resort and Spa
              Key West, Florida Keys, Florida
              • Beachfront
              • Business
              • Kid-Friendly
              • Luxury
              • Resort
              • Romantic
              The Hyatt Key West Resort & Spa underwent a multi-million dollar renovation in 2007. The result is a modern tropical resort right on the water's edge. All 118 rooms have a soothing beach-inspired feel and are complete with private balconies. Bathrooms are spacious and modern with funky elevated and…
            13. Sheraton Suites Key West
              Key West, Florida Keys, Florida
              • Kid-Friendly
              • Value
              The Sheraton Suites is a mid-sized, all-suite hotel that's across a busy street from Smathers Beach. Suites are spacious with a cozy living area separate from the bedroom, and bathrooms have big marble showers. The hotel is well maintained and amenities are numerous, including a bright, gym, big and…
            14. The Gardens Hotel
              Key West, Florida Keys, Florida
              • Adults-Only
              • Boutique
              • Historic
              • Luxury
              • Romantic
              Once Key West's largest private estate, the four-pearl Gardens Hotel is an intimate, 20-room boutique that caters to vacationers seeking romantic getaways. It's at the center of Old Town, a huge plus since Key West is best enjoyed on foot. The rooms range from standards with garden and courtyard to…
            15. The Paradise Inn
              Key West, Florida Keys, Florida
              • Adults-Only
              • Bed and Breakfast/Inn
              • Boutique
              The 18-room Paradise Inn is an adult-only boutique hotel with historic flair located in Key West’s Old Town close to Duval Street. The upper-middle-range inn is quaint and relaxed. Management is committed to preserving the peaceful elegance of the hotel and its restored cigar-maker cottages, and or…
            16. Ibis Bay Beach Resort
              Key West, Florida Keys, Florida
              • Beachfront
              • Kid-Friendly
              • Romantic
              • Value
              The 81-room Ibis Bay Beach Resort is a cozy, quirky, 1950s-throwback with lots of personality and plenty to do. Built in 1954, the three pearl property combines a vintage vibe with modern comforts -- plus wild animals and lots of hammocks throughout the grounds. The resort has a relaxing pool, and a…
            17. Duval Inn
              Key West, Florida Keys, Florida
              • Boutique
              • Historic
              • Kid-Friendly
              The Duval Inn is about a block away from old Key West’s shops, restaurants, and bars but is an oasis of sorts with a jungle-like courtyard and small pool. Each room is rich in character and individually decorated. Families are welcome here and can stay in adjoining rooms. Some of the rooms have full…
            18. Key West Marriott Beachside Hotel
              Key West, Florida Keys, Florida
              • Kid-Friendly
              • Romantic
              The 222-room Marriott Key West Beachside Hotel is a waterfront property located away from the party atmosphere of downtown Key West (a free shuttle takes guests to and from the action). There is a private, man-made beach along with a big, zig-zag shaped pool, and on-site fitness center with daily -…
            19. Angelina Guest House
              Key West, Florida Keys, Florida
              • Bed and Breakfast/Inn
              • Historic
              • Value
              The Angelina Guest House is a former 1920s bordello and gambling den turned into a charming Key West bed-and-breakfast teeming with Southern hospitality. The 13-room budget property welcomes adults only, and maintains a quiet, peaceful atmosphere; the owners request that guests leave their partying…
            20. The Weatherstation Inn
              Key West, Florida Keys, Florida
              • Boutique
              • Historic
              • Romantic
              • Value
              This charming, eight-room property is housed in a historic building on a quiet street in Old Town Key West, within walking distance to some of the major tourist attractions, and to a couple of good beaches. Each of its rooms has a distinct character and few amenities (a flat-screen TV and little but…
            21. Coconut Mallory Resort And Marina
              Key West, Florida Keys, Florida
              • Kid-Friendly
              • Value
              The mid-range Coconut Mallory Resort and Marina is an affordable condominium-style property that’s geared toward families with a location that -- albeit removed from the excitement of Key West -- offers direct marina access and 18 boat slips. The 34-room resort has two outdoor pools, a hot tub, and…
            22. Knowles House B&B
              Key West, Florida Keys, Florida
              • Bed and Breakfast/Inn
              • Historic
              • Kid-Friendly
              • Romantic
              The Knowles House B&B is an historic conch house near Duval Street and the waterfront with eight individually decorated guest rooms. This charming, mid-range property serves homemade breakfast on a tropical patio, and offers a tiny outdoor pool, hot tub, and rooftop sun deck. Guest rooms have TVs, a…
            23. Ambrosia Key West Tropical Lodging
              Key West, Florida Keys, Florida
              • Boutique
              • Kid-Friendly
              • Romantic
              This charming mid-range bed-and-breakfast is close enough to Key West action to be considered convenient, but secluded enough to still be a relaxing retreat. With the Ambrosia within fast walking distance of Duval Street, Mallory Square, and the historic seaport, guests often venture out after the a…
            24. Merlin Guest House Key West
              Key West, Florida Keys, Florida
              • Bed and Breakfast/Inn
              • Historic
              • Romantic
              The 20-room Merlin Guesthouse is a mid-range bed-and-breakfast shaded by tropical greenery on a 1930-built property that’s one block from Duval Street. This charming retreat has a lush courtyard and breakfast terrace, a quiet outdoor pool, and a front porch with chairs for lounging. Stylish rooms or…
            25. Parrot Key Hotel and Resort
              Key West, Florida Keys, Florida
              • Luxury
              The 148-room Parrot Key Hotel & Resort is located on the Florida Bay, a bit away from Key West’s popular Duval Street and entertainment district. Though photos show lounge chairs in the sand along the water’s edge, the property isn’t technically on the beach, but there is access to water sports and…
            26. Eden House
              Key West, Florida Keys, Florida
              • Historic
              • Kid-Friendly
              • Value
              Eden House has had the same owner for nearly 40 years, and numerous loyal customers return year after year for the affordable prices and friendly vibe. Rooms can be bare-bones, especially the semi-private ones with shared bathrooms and no TVs or mini-fridges. Even the higher-level rooms are fairly a…
            27. Crowne Plaza Hotel Key West - La Concha
              Key West, Florida Keys, Florida
              • Historic
              • Romantic
              The 160-room Crowne Plaza Hotel Key West - La Concha is a historic landmark dating back to 1926, but this upper-middle-range property now appears has plenty of glitzy modern appeal. Rooms have vintage Caribbean-chic decor and feature flat-screen TVs, mini-fridges, and coffeemakers, and some have the…
            28. Orchid Key Inn
              Key West, Florida Keys, Florida
              • Boutique
              • Romantic
              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, an…
            29. Coco Plum Inn Bed and Breakfast
              Key West, Florida Keys, Florida
              • Bed and Breakfast/Inn
              • Historic
              • Romantic
              Offering what is easily one of the more scrumptious breakfasts of any bed and breakfast in Key West, Coco Plum is a lovely, if slightly dated, mid-range guesthouse just a block off bustling Duval Street in the heart of old town. With made-to-order breakfasts and a small outdoor pool, it's slightly…
            30. The Conch House Heritage Inn
              Key West, Florida Keys, Florida
              • Bed and Breakfast/Inn
              • Historic
              • Romantic
              The 10-room Conch House Heritage Inn is an historic, competitively priced retreat in Old Town Key West in walking distance to Duval Street. This charming, mid-range property draws repeat guests with its warm hospitality, free homemade breakfast, daily happy hour, and tropically landscaped outdoor a…
            31. Best Western Hibiscus Motel
              Key West, Florida Keys, Florida
              • Beachfront
              • Kid-Friendly
              • Value
              The Best Western Hibiscus Motel is a 61-room, three-pearl motel-style property located within walking distance to many tourist attractions in historic Key West. Rooms are clean and comfortable with basic furnishings but don't offer amazing ocean views. The property is geared toward travelers who to…
            32. Old Town Manor
              Key West, Florida Keys, Florida
              • Adults-Only
              • Bed and Breakfast/Inn
              • Historic
              • Romantic
              The 14-room, mid-range Old Town Manor is an adult-only bed-and-breakfast set in an historic Victorian mansion, just a block from Key West's popular Duval Street. The two-house Manor is cozy and warm with tons of character, including a grand front porch with rocking chairs, and lush gardens where can…
            33. Cypress House Hotel: Key West
              Key West, Florida Keys, Florida
              • Boutique
              • Historic
              • Romantic
              One of the six properties included in Historic Key West Inns, the tastefully renovated and mid-range Cypress House, on a quiet corner in old town, has 22 spacious rooms, and a comfortable outdoor pool area. It's a block from Duval Street, the seaport, and Key West’s many shops, restaurants, and Free…
            34. Silver Palms Inn
              Key West, Florida Keys, Florida
              • Boutique
              • Romantic
              One of the only modern hotels in Key West -- ironically situated in the Historic District -- this upper-mid-range, 50-room property is an ideal vacation spot. Close to the action but far enough away to also be quiet, guests can walk to Duval Street or spend the day lounging by the hotel's lovely The…
            35. Truman Hotel
              Key West, Florida Keys, Florida
              • Boutique
              The 35-room, mid-range Truman Hotel is a trendy boutique property located in Key West’s Old Town, two blocks from Duval Street’s nightlife, restaurants, and shops. The Truman is one of Key West’s newest hotels, standing out from the many genteel Southern inns with its modern decor and bright pops of…
            36. Casa 325
              Key West, Florida Keys, Florida
              • Boutique
              • Romantic
              With an unbeatable location tucked into an alley steps from Duval Street, Casa 325 is surprisingly quiet in spite of the many bars, restaurants, and shops surrounding it. There is an outdoor pool, with plenty of lawn chairs and umbrellas for shade. Rooms come in several sizes -- from a One-Bedroom a…
            37. The Grand Guesthouse
              Key West, Florida Keys, Florida
              • Bed and Breakfast/Inn
              • Historic
              • Romantic
              • Value
              The Grand Guesthouse is a cozy, value property with 10 rooms and a quiet setting within walking distance of Duval Street. Free breakfast is served on a worn wood patio, and bike rentals and touring assistance are offered. Guest rooms are decorated with tropical flair and local artwork, and have and…
            38. Southernmost Inn
              Key West, Florida Keys, Florida
              • Adults-Only
              • Bed and Breakfast/Inn
              The 38-room, lower-middle-range Southernmost Inn was converted from a late-1800s cigar factory and renovated in 2014. The adult-only inn draws many couples, and feels like a classic Key West bed-and-breakfast, with a welcoming porch, plentiful outdoor space for lazy days, antique furniture, and two…
            39. Alexander's Gay and Lesbian Guesthouse
              Key West, Florida Keys, Florida
              • Boutique
              • Historic
              • Romantic
              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…
            40. The Saint Hotel Key West, Autograph Collection
              Key West, Florida Keys, Florida
              • Boutique
              • Historic
              • Romantic
              The three-and-a-half-pearl Saint Hotel Key West emits a sexy vibe with its "play naughty, sleep saintly" slogan. Situated next to the buzzing nightlife on Duval Street and within easy walking distance of top sights, the hotel's location is one of its key features. Also a standout are the pretty fare…
            41. Key Lime Inn Key West
              Key West, Florida Keys, Florida
              • Boutique
              • Romantic
              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 a…
            42. Avalon Bed and Breakfast
              Key West, Florida Keys, Florida
              • Bed and Breakfast/Inn
              • Historic
              • Romantic
              The 19-room mid-range Avalon Bed and Breakfast is a charming historic property on the quieter end of Duval Street within walking distance of bars, restaurants, and major attractions. Rooms are elegant, with white fabrics and warm hardwood throughout. Mini-fridges are an added bonus. A free breakfast…
            43. Artist House
              Key West, Florida Keys, Florida
              • Boutique
              • Historic
              • Romantic
              Some guests might steer clear of the home of the haunted stuffed doll that inspired the movie "Chuckie," but Artist House, one of the most photographed houses in Key West, is immaculate, bright, colorful, and welcoming, with nothing spooky about it. This restored Victorian mansion serves European at…
            44. Atlantis House
              Key West, Florida Keys, Florida
              • Boutique
              • Romantic
              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…
            45. Best Western Key Ambassador Resort Inn
              Key West, Florida Keys, Florida
              • Kid-Friendly
              • Value
              Situated on the far side of the island away from Key West's main attractions but close to the airport and across the street from the beach, Best Western Key Ambassador is a mid-sized value hotel offering decent amenities for people who don't mind being away from the center of the action. With a pool…
            46. Lighthouse Court Hotel in Key West
              Key West, Florida Keys, Florida
              • Boutique
              • Historic
              • Romantic
              Part of the Historic Key West Inns chain, the Lighthouse Court consists of 40 guest rooms scattered throughout 10 conch buildings. Palm trees shade the property and the courtyard pool is flanked by the Mojito Bar and Cafe, which offers light fare and cocktails. Still, travelers may have to contend a…
            47. Chelsea House Hotel in Key West
              Key West, Florida Keys, Florida
              • Boutique
              • Historic
              • Romantic
              • Value
              Composed of two houses, one built in 1891 and the other in 1905, this beautiful, mid-range Key West property is a classic part of the Historic Key West Inns and located in the area’s historical district. Last renovated in 2005 and with 33 rooms available, the hotel has tropical, rustic decorations…
            48. Almond Tree Inn
              Key West, Florida Keys, Florida
              • Boutique
              • Kid-Friendly
              • Romantic
              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 and…
            49. Sunrise Suites Resort
              Key West, Florida Keys, Florida
              • Kid-Friendly
              • Value
              The mid-range Sunrise Suites Resort is a quiet, family-oriented condo complex near Key West International Airport, on the opposite end of the island from the bustling Historic District. It’s a solid choice for travelers seeking spacious, residential-style condos in exchange for proximity to top The…
            50. Southernmost Hotel
              Key West, Florida Keys, Florida
              • Business
              • Kid-Friendly
              • Luxury
              • Romantic
              The 118-room Southernmost Hotel is an upscale property a block away from Key West’s Southernmost Point and the beach. The convenient location is within walking distance of restaurants, bars, and several attractions, yet it’s removed enough from the action to provide a quiet stay. The hotel has chic…

            Like Us on Facebook! You'll Be Glad You Did