Last Updated on November 20, 2022
Disclosure: Our writers only recommend vacation rentals they’ve experienced firsthand, and all opinions expressed are their own. This post may contain affiliate links that allow us to earn a small commission at no additional cost to you.
The Florida Keys beckon travelers from around the world with abundant sunshine, endless ocean and lively nightlife and festivals. For every type of traveler there is an accommodation suited for where to stay on Key West.
Whether you want to hobnob with Key West’s famous six-toed cats, or pamper yourself in refined luxury, where to stay on Key West is simply a matter of taste, there are no shortage of options.
Where to Stay in Key West FL
VRBOs for Big Groups in Key West
With 57 reviews on VRBO.com and a 4.8 rating, Waterfront at the Galleon Resort in Old Town is where to stay in Key West FL with a big group. It sleeps eight comfortably with a king bed in the master, a queen bed in the second bedroom and loft & a queen pullout in the living room.
Don’t take our word for it, here’s an actual review left in October of 2022: “This was our second time staying in this specific condo and it was all we expected. It is a wonderful unit overlooking the marina with fabulous sunrises! Communication with the unit owner was again effortless and check in was just as easy. Would definitely recommend to anyone looking for a place to stay when traveling to Key West.”
Groups keen on affordability while still wanting a premiere Key West experience should consider this Oceanfront at Smathers Beach property sleeping 7 and priced at only $265 per night.
VRBO for Family of Four(ish)
Where to stay on Key West with a family? Try Pineapple Cottage a half block from bustling Duval Street with its own PRIVATE POOL! Less spendy is this Truman Annex townhome two blocks from Duval Street and four blocks from the nightly Sunset Celebration at Mallory Square. The recently opened Truman Waterfront Park, including a free waterpark for the kids, is a short walk or two-minute drive from the property.
Luxury Resort: The Marker Key West Harbor Resort
Before any traveler embarks on an epic Florida Keys road trip, the first and most important task is to book their stay. We urge travelers to let the “Keys Disease” take over and stay by the historic seaport and catch the ultimate vibes at The Marker Key West Harbor Resort. Recently listed as the #1 resort in the Florida Keys by Condé Nast Traveler Readers’ Choice Award, guests can partake in the hotel’s daily pool area programming from Key Lime turndown service to the Reggae Sunday poolside concerts.
Ideally located on just steps from the lively Duval Street and Mallory Square, this modern, waterfront resort offers a hidden sanctuary of lush tropical grounds, three saltwater pools, an open-air restaurant and bar for al fresco dining. Each of the resort’s 96 spacious and luxuriously appointed guest rooms feature a private balcony, perfectly appointed design elements and Key West-inspired touches.
Best Hotel For Couples in Key West on a Budget
With rates starting for less than $200 per night, the Fairfield Inn & Suites Key West at the Keys Collection offers location, value, on site pool, free breakfast and wifi. This is where to stay in Key West FL for those who don’t intend to spend the majority of their vacation inside.
Florida Keys Road Trip
Half the fun of visiting Key West when driving from the mainland is getting there. Now that you know where to stay on Key West, it’s time to start planning your trip. Popular attractions, restaurants and parks line the 100 miles from Key Largo, where U.S. Highway 1 enters the Keys, all the way down to Key West.
As you begin the descent down to the Conch Republic, Key Largo holds destinations worthy of a pit stop. Sundowners is a long time local favorite restaurant serving sunsets, sandwiches, steaks and seafood on the Florida Bay. While on the back dock, visitors can feed the tarpon or sign up for parasailing with family and friends.
Just a few miles down is Pirate Cove Water Sports. Those looking for a bit of action at the start of the road trip can rent jet skis, paddle boards, kayaks and even go snorkeling to explore the marine life native to the Keys.
One last stop is the famous Blonde Giraffe Key Lime Pie Factory for all things key lime. At the Blonde Giraffe, key lime lovers can savor their famous key lime pie while relaxing in the serenity garden and also purchase key lime-flavored cookies, pecans, almonds, malted balls and more.
Next up on the road trip is Islamorada, the sport fishing capital of the world. Consisting of four islands, Islamorada is a popular destination with several eateries and local stores for all to enjoy.
The first stop is the Islamorada Fish Company, a restaurant overlooking the bayside of the Florida Gulf Coast with legendary sunsets and soft bay breezes. After a meal, patrons can walk over next door and shop at Bass Pro Shops for all things nature and nautical.
Robbie’s Marina of Islamorada is a must-visit stop in the Florida Keys. From hand-feeding the massive tarpon to stocking up on handcrafted souvenirs from the local shops, there’s an activity for everyone.
Big Pine Key
Vacationers looking to transport to a quiet oasis can pull over to Big Pine Key and take a break from the road. This area of the Florida Keys is surrounded by wildlife trails, water-borne activities and white sand beaches. The Bahia Honda State Park has some of the best views of the island strip with clear waters and breathtaking sunsets, serving as a great refuel and recharge stop from the road trip.
While in Big Pine Key keep your eyes peeled from wild deer as you step into the National Key Deer Refuge, a national park made to protect and preserve deer and other wildlife in the Keys.
RELATED: Stay in a TINY HOUSE near Big Pine Key and Bahia Honda State Park! (below)
Just outside of Key West is Stock Island, the laid-back vintage spot that authentically channels the spirit of Old Key West. For a trip before your trip, Stock Island is home to some of the best restaurants and water activities for all to enjoy.
The Hogfish Bar & Grill offers all who step foot fresh seafood with panoramic waterfront views.
Next up is Fun in the Sun boat charters and rental company, promising a good time under the Florida Keys sun with paddle boarding, kayaking, bike rentals and more.
As travelers arrive in Key West, they can escape to island time and check out historic attractions, waterfront resorts and one-of-a-kind local eateries. Just a few steps away from The Marker is the Funky Rooster, an eclectic coffee house and wine bar channeling all the island vibes with local art.
Enjoy breakfast, lunch, happy hour or dinner at Pepe’s Cafe, the oldest eatery in the Florida Keys and second in Florida.
Learn more about the fascinating history of Key Lime Pie and where else to find the best pies in the city on this podcast, a perfect companion for your Florida Keys road trip.
Finally, you can’t leave Key West without checking out one of the many historic attractions including The Hemingway House, the 1930s residence of famous author Ernest Hemingway; Little White House, former home of president Harry S. Truman; or like any good historic town, thrilling Ghost and Gravestone Tours.beachhistoric