Santa Maria Suites Rating: 4.0 Pearls
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 excellent value to families, couples, and groups of friends traveling together.
Eden House Rating: 3.0 Pearls
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 plain, though, with small bathrooms, simple (verging on bland) decor, and very little furniture (aside from the apartment-style rooms). This historic hotel does have a nice pool courtyard surrounded by palm trees, lovely grounds with deck areas, hammocks, and koi ponds throughout, and tons of freebies (Wi-Fi, parking, and happy hour) that make it a good value.
Southernmost Hotel Rating: 4.0 Pearls
Southernmost Hotel is a small beach hotel with a great location. It's on Duval Street, at the opposite end as all the bars and restaurants; it's only a five-minute walk from the action, yet is far enough away to provide a quiet stay. The hotel has pleasant rooms -- though some are more modern than others -- and appealing bathrooms with stall showers. Southernmost borrows its beach, pier, and one restaurant from its sister property, Southernmost on the Beach, but guests report that this does not diminish from the experience, and rates here tend to be cheaper.
The Grand Guesthouse Rating: 2.5 Pearls
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 mini-fridges and free Wi-Fi.
Angelina Guest House Rating: 2.0 Pearls
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 on nearby Duval Street. The Angelina offers a lovely lagoon-style pool, bike rentals, and homemade cinnamon rolls included in the free breakfast. Accommodations are clean and well cared for, ranging from simple rooms with shared bathrooms to efficiencies with refrigerators and microwaves; guest rooms don’t have phones, and only one has a TV.
Sheraton Suites Key West Rating: 3.5 Pearls
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, well-equipped gym, big pool with tiki bar, and business center. Downtown Key West and Duval Street are a six-minute drive away -- a hotel shuttle offers free transportation until 11 p.m. -- making this hotel a better fit for families seeking sand and sun than people looking for nearby nightlife.
Hawks Cay Resort Rating: 4.5 Pearls
Hawks Cay Resort has the feel of a small village, due to its massive size and many amenities -- the property even has its own 85-slip marina. Many guests arrive by boat, as the resort is located on Duck Key, a secluded spot far from Key West's main airport. The property largely attracts families looking for a quiet vacation, thanks in part to family-friendly features such as a dolphin experience, kids' club, and multi-bedroom villas. Plus, the beach has calm waters which appeals to families, but its secluded location gives it a bit of a romantic feel as well. Its long list of amenities, which are all gorgeous -- from the spa to the pool to the three restaurants -- and its upscale rooms with updated amenities make it a great choice. And though it is a luxury property, it offers a lot of bang for your buck.