Sunset Key (private island)

Sunset Key Cottages

★★★★★

Sunset Key Cottages is the most exclusive stay in Key West and one of the most memorable in Florida. The resort occupies a 27-acre private island about 500 yards across the harbor from Mallory Square — close enough to see the sunset crowds, far enough that you will not hear them. There are no cars on the island; guests and their luggage cross on the resort's launch from the dock at 245 Front Street, and the island's quiet lanes are made for walking. Accommodation is in one- to four-bedroom cottages in classic Key West style, each with a veranda, ocean or garden views, a full kitchen and generous living space, and some with private pools. The island has a white-sand beach for guests, a pool and on-island dining, and the atmosphere is hushed and residential, more a private village than a hotel. It is ideal for honeymoons, anniversaries and family reunions: a four-bedroom cottage can house a multigenerational group, and the kitchens make longer stays practical. And when you want the town, the launch puts Duval Street fifteen minutes away. The trade-offs are significant: prices are among the highest in the Florida Keys, everything on the island costs a premium, the launch schedule shapes your evenings out, and the quiet that couples love can feel isolated to travelers who want nightlife on their doorstep. For a once-in-a-lifetime stay, though, nothing else on the island compares.

What makes it special is the separation. Key West is small, busy and loud in the evenings, and Sunset Key turns that into a view rather than a soundtrack: you watch the sunset from your veranda or the beach with Mallory Square's crowds silhouetted across the water, then walk home along quiet lanes lined with palms. Days revolve around the beach and pool, cooking in your own kitchen if you like, and short trips into town for museums, restaurants and boat excursions from the seaport. The cottages are well spaced and landscaped, giving a sense of privacy uncommon in Key West.

Planning: book well ahead for winter and holidays, when cottages sell out. Choose ocean-view cottages for the full sunset experience, and larger cottages for families or friends traveling together. Ask about the launch schedule and how luggage, groceries and late returns work; the crossing is short and frequent, but it is still a boat ride. Dining reservations on the island fill on busy evenings, so reserve early. Many guests stock their kitchens on arrival and save the restaurants for special nights, which also softens the cost of a longer stay. Children are welcome, and the beach and pool suit families with young kids who want space to play without traffic.

Who it suits: honeymooners and anniversary couples, families and groups who want a private cottage and kitchen, and anyone who wants Key West's beauty without its noise. Travelers on a budget or those who want to stroll home from Duval at 2 a.m. should stay in Old Town instead. Pair a stay with sunset on your veranda, a morning at the Hemingway Home across the water, and a day trip to the Dry Tortugas from the seaport.