Private Island in Florida Keys: Sunset Key

Sunset Key, just off of Key West, Fla.

Sometimes life is unpredictable in the best ways. The absolute best ways.

I’ll explain. Back in April, when I spontaneously went to Key West for 24 hours with my roommate Lindsay, we stood in Mallory Square watching the sunset. I pointed across the water at an island just in the distance which looked to have a bunch of cottages on it. “Imagine living over there,” I said dreamily. “Yeah, there’s a Westin over there,” Lindsay informed me, adding that she had thought about taking her mom to stay there before. “It’s a private island. The hotel rooms are basically little houses.”

The irony of this conversation is that neither of us had any idea that about a month later, we would be staying on that island.

Last month, I got the opportunity to stay at the Westin in my own cottage on my own private island. And of course, I brought my roommate with me. It was only the right thing to do, given our previous conversation. It was an I-can’t-believe-I’m-here kind of weekend.

Here’s a look at our accommodations:

It all starts with a ferry ride. The only way to get back and forth between Sunset Key and Key West is by a 10-minute boat ride. The ferry runs every half hour during the day and is on call late at night. This is where it docks.

This was the backyard of my cottage. One of my No. 1 dreams in life is to live on the beach. Like, be able to walk into my backyard and walk a few steps to the ocean. For four days, that dream came true on Sunset Key.

In fact, my bedroom wall was practically all-windows, and understandably, I kept the blinds open almost the entire time I was there so I could just stare at the endless blue. (Side note: my cottage was a 2-bedroom, 2.5-bathroom home complete with a kitchen and living area. My roommate and I each lounged on our own king beds.)

My cottage featured a wraparound porch, complete with tables and chairs, and even rocking chairs. Every morning, a picnic basket was delivered with complimentary breakfast – fruit, muffins and pastries – and the fridge was stocked with complimentary juices. Does life get any better than that?

The inside contents of my basket. The quickest way to my heart is oranges.

This was Lindsay’s favorite part: Hammocks lined the beach behind the cottages. I think she had permanent marks on her back from the hammock ropes from relaxing in them all weekend.

A must-do on the island: a sunset dinner at Latitudes. This is the table Lindsay and I sat at, watched the sunset, sipped wine and ate steak and seafood.

Lindsay, enjoying our sunset dinner.

I am all about dinner with a view, and Latitudes is where I experienced literally the best dinner view I’ve ever had. I also didn’t even edit this photo. This is legit what the sky looked like.

Of course, if you don’t want dinner with a view, you can always relax in your cottage and whip something up in the kitchen. I’m still all about view, though….

But why eat in your kitchen when you can eat just like this? The Westin has great restaurants over in Key West too. These were some yummy conch fritters at the Westin Key West’s Bistro 245, just across the water from Sunset Key.

Possibly my favorite cocktail, ever. The Westin’s Key lime coolada. I think I ordered one during every meal out, no matter how much the flavor clashed with whatever I was eating. They are just. that. good.

Me, in Sunset Key. You almost can’t even tell how ridiculously sunburnt I am. Win win.

I went to the beach every day in Sunset Key, and each time this adorable 20-something waiter would trudge through the sand in his long pants to take the orders of his guests. He was so genuinely eager to be accommodating and I immediately fell in love with his sweetness. He would always emphasize that anything we wanted, he would get for us. So the last day I was there, he offered me “anything” again, and I had an idea.

“This is going to send weird, but can you take a picture of me?” I asked him, explaining that I needed it for work. I warned him I was very picky about pictures of myself and it would probably take several shots. Without hesitation, he agreed. Then we spent the next 30 minutes taking pictures, and he instructed me to do all kinds of model poses, which I awkwardly attempted. It was a real testament to the staff as a whole at the Westin at Sunset Key, and how devoted they were to making the stay perfect, just like a private-island getaway should be. Even when I went to the spa, my aesthetician told me all of her favorite spots in Key West, giving me tons of ideas for things to check out on the island (which I’ll write about in another post). After the treatment, she went and wrote down the list, which contained at least 10 shops, restaurants and bars. The experience definitely made me realize that no matter how private a vacation may be, it’s those added little touches from contact with people that make the trip.


  1. Holly says:

    If you stayed in the Kiwi cottage that is where I stayed the week of my wedding. It is a gorgeous place and the spa is amazing

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