Hotel, motel, Holiday Inn? It’s hard to discern where to stay, when hotels, rental homes, and bed and breakfasts are around every corner! So we’ve slept our way around town (no it’s not what you’re thinking, but) to compile a list of the best places to rest your head upon your next Key West vacay!

Want a Bed & Breakfast? Try The Mermaid & the Alligator

Elegant, warm, island-sophisticated, The Mermaid and The Alligator is a 1904 Victorian Home, located in the heart of Old Town Key West. A stay in one of their rooms tucked away in paradise includes all the niceties and hospitalities of a B&B from a delicious breakfast every morning to a complimentary glass of wine each evening while you contemplate your dinner plans.  Their motto, “let our home be your Key West home” keeps their loyal guests returning year after year. The best news is, a stay with them is only 4 blocks from the start of the Southernmost Food Tour!

Or The Speakeasy Inn!

Right on the 1100 block of Duval you’ll find this historic gem. Built in 1889, The Speakeasy Inn is easy to miss, but hard to forget! Owner and cigar selector from Gato Cigar Factory, Raul Vasquez, has made his mark in Key West as both a Inn owner and Rumrunner! This quaint and casual roost has a magnetic, laid-back atmosphere that will keep you at their door step by enticing with specialty rum flights and Caribbean cocktails mixed by their friendly and colorful bartenders inside the lobby Rum Bar. The Southernmost Food Tour stops here briefly to grab Rum Runners to-go and get a look around. The breezy porch just outside the bar overlooks Duval–perfect for people-watching the afternoon away. It’s guaranteed you’ll loose track of time, so you’ve been warned!

Photo // Yolorum

Want a Vacation Rental Home?
Try Vacasa

Crafted, catered, curated. Vacasa manages and brokers a wide variety of adorable to lavish Key West rental properties that are perfect for any sized group that wishes to stay in more private accommodations. Their website is streamlined and user-friendly, but their helpful staff would be just as happy guiding through finding your perfect rental on the phone.

Or Truman Annex!

A Navy base from 1906-1970’s, Truman Annex is now the premier neighborhood in Key West, without question. It’s peaceful and tranquil fenced-in parcel is a respite from the raucous mayhem that lies just beyond it’s Presidential gates. You can’t deny the location–it’s literally a stones throw from Duval Street and Front Street making it “The” place to be. The Truman Little White House, a vacation-home-turned-museum, is the tourist cherry on top as a fabulous morning or afternoon tour. Face it, if it’s good enough for a president, it’s good enough for you.

Want a hotel?
Try The Saint Hotel

The Saint Hotel is true Key West heritage. Built in 1830’s, it was originally The Southern Cross.  The New Orleans Saint Hotel owner purchased and remodeled the 37 rooms in 2014, and you’ll love what they’ve done with it. A proud part of the Marriott Autograph Collection, it’s home to a richly decorated interior. Velvets, leathers, fur…it’s a texture fetish paradise. We recommend heading into the Pilar Bar for a signature rum drink and some tantalizing happy hour bar menu items that bring even the locals to the tables.

Or La Concha!

Boasting of marble floors, private baths, luxurious décor, an elevator, and sweeping ocean views, the La Concha hotel was considered to be the height of elegance and modern convenience for 1926.  Developer Carl Aubuchon’s luxury hotel was the first of its kind on Key West. Many famous guests have stayed at the centrally-located landmark over the years, including literary legends and dignitaries like Ernest Hemingway, Tennessee Williams and Harry Truman. Now days, the only way to access their breathtaking sunset views from the top level is to book a spa treatment. Oh, darn. haha.