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Key West Time
October 16th
11:14pm · 81°F

A Key West Vacation Rental Story: "Renting in Key West? A Win-Win!"


If there is a common denominator for Chris Sexton’s family vacations, it is seeking out local experiences in new places. So, when he decided to give Key West a whirl on the advice of a business associate, it felt easy to take another leap of faith and rent a vacation home for the very first time.

Not ‘Just Another Vacation’

“Some friends of ours said, ‘If you stay in a hotel, it’s just another vacation. But, if you rent a house, it’ll be a special vacation,’” Chris says. “I thought, I’m going to give it a try.”


While searching the Internet for a place large enough for him, his wife, Tammy, and their 21-year-old son, Brock, as well as extended family visiting from Texas, Chris kept returning to Vacation Homes of Key West. He finally settled on Tropical Tranquility, a home with four bedrooms, including one in a private guest cottage.

Sweet Seclusion

The gated entrance to this resort-style property – which started life as a humble "shotgun" cottage – is set back off an artist’s lane in the heart of Old Town Key West. It is so secluded that Chris, who drove his family down from Miami in a rented van, almost missed it.

“You could drive right by this house, because of the foliage, plants and trees around it,” he says. “Once we went in, we were absolutely elated. We thought, ‘How are they hiding all of this back here?’” Just beyond the front gate, a brick path meanders through the manicured garden to a lagoon-style pool with a waterfall. Just beyond, the path widens into a courtyard, flanked by fragrant trees and flowers.


“The pool was a huge hit. It was quiet and felt absolutely secluded from everything else. You would not have known there was a major street a half block away,” Chris says.


Loving the Rental Lifestyle

Chris took to the vacation rental lifestyle from the start. He loved cooking a big breakfast for everyone each morning and the families stayed in for dinner three nights during the week. They loved having comfortable common areas where they could spend time together, as well as privacy whenever they wanted it.


Chris attributes the positive experience to VHKW. “Obviously, they’ve done this before,” he laughs. “They knew the types of things that you would have questions about and they answered them on the front side, so there were no communication issues. I would recommend them to anyone, period.”

During the day, the families took in the sights. They loved the Old Town Trolley and the aquarium. One afternoon, they ferried out to a place where they could go parasailing, scuba diving and jet skiing.


Listening to Locals

Rather than stick to a guidebook, Chris preferred to follow up on recommendations from locals – taxi drivers and bartenders.


“I’ve always felt like that if you have a preconceived agenda and it doesn’t meet your high expectations, you’re let down,” Chris says. “We approach it this way as a family: we have a few things we say we want to do and we make sure we do those things. But, the gaps in between we fill with local establishments and experiences.”

Will they be back? “Oh, there’s no doubt!” Chris says. “Without question, I would go right back to the same house. The pool, the layout and the proximity to Old Town would just be ideal for a friends retreat.”


Favorite Things


Renting Scooters

We all rented scooters and rode them all over the island. Some people say, ‘Really? Just riding a scooter was fun?’ It was absolutely fun! Going down the narrow streets and seeing different areas, going where you want to go and parking nearly anywhere you want to park. It was a home run.”

Soaking In the Spirit of Key West

“You don’t have to do anything – it’s all there for you, if you’re willing to take a short stroll down and stand and listen and observe and enjoy.”




Celebrating Sunsets

“The fanfare that goes on at sunset celebrations, it didn’t get old. We went back again and again to listen to our favorite blues performer.”

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