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We’ve gone through dozens of applications and viewed numerous homes to bring you some of the best vacation homes and owners that Orlando has to offer. We’re proud to compile this list of unique vacation homes and outside-the-box thinking owners. We think each of these homes deserves to be recognized and certainly should be at the top of your list for those of you traveling to Orlando. Check out this week’s Vacation Home of the Week!!


Platinum Key Villa










Location: Kissimmee, FL
Neighborhood: Windsor Hills Resort
Owner Booking Weeks: 40
Management Booking Weeks: 10

Why Owners Chose This Home:  “This home was strictly an investment and the numbers were the most important factor. Taking that into consideration, Windsor Hills seemed like the most obvious choice as it was pushing the standard to the next level on vacation homes. It was just an Orange Grove at the time and the home was purchased site unseen, not even built yet, but the location and amenities were what sold it it”

What Makes This Home Unique: “Platinum Key Villa has flat screen TVs in every bedroom, is professionally decorated by an interior designer and offers only the highest quality linens and towels. There is nothing low quality in this home. Many guests refer to it as home-only better”

Marketing Strategies: ” Word of mouth up in Toronto seems to be the biggest ticket for the homes but also VRBO and Homeaway have really helped. Having multiple homes is also a huge plus because you get six times the amount of inquiries and can shift them from one home to another if one is not available.”

The Pink Flamingo’s Review: John is a businessman, investor, real estate agent and now a professional vacation home owner.  He knew from day one that he was going to make this work. He owns five vacation homes in Kissimmee. All of them are in Windsor Hills except for his most recent purchase in the new community of Calabria. His business plan is only to specialize in high end vacation homes in the nicest communities in the area because the rents are so much higher on a high end home, making it possible to turn the vacation home into a very profitable investment.

Windsor Hills Resort

He purchased his first vacation home in Windsor Hills as a prototype and wanted to see how it would go. After having so much success he went on to purchase four more vacation homes and he’s not done yet! Because John does this for a business and an investment (this is in no way his full time business, this is more like his hobby!) the numbers have to work on the homes.  Being in real estate up in Toronto and understanding how property investments work, he analyzes the numbers on every property before making a purchase. His strategy of only buying new homes in upper end communities seems to be working out very well for him as all of his homes have been booked almost the entire year at top rates. When it comes up a luxury vacation home, renters don’t seem to have an issue paying more money to stay in the home as there is a market for those type of renters.

What I like about John’s marketing strategy is that, even though he owns five homes and it’s a profitable business for him, he still treats everyone of them like it’s his only home. John and his family travel to Orlando often and enjoy their luxuries of their homes. They will stay at what ever home is available at the time. Taking on their fifth home has offered them more vacation time as it’s just getting up and going and during the downtime they have been able to come down and enjoy it more. He also uses his homes for his business retreats with his business partner. Being able to vacation and write it off at the same time is such a perk!

One very smart tactic that he did to save time and marketing dollars is that he purchased two exact same homes, right next door to each other and decorated them both exactly the same way.  He did this so he can market them both under one ad and when guests inquired on one, if it’s booked he could just put them in the other without having to upsell or downsell them on a completely different home. Even the little things like the title of his website, makes you feel like your discovering something new and exciting. He could have said Keys2YOURvacation but instead he wanted to make it all about the true meaning behind owning a vacation home, enjoying someone else’s private home! He very tastefully named each of his homes after the theme of his website, “The Key”. Each home unlocks a key to a different vacation, I love that he even went as far as having a logo created for his vacation home business.

All of John’s homes are gorgeous. They are all professionally decorated by an interior designer and located on great lots within Windsor Hills.  John seems to have a knack for choosing great locations, probably because of his real estate background, and offering everything in a home that a renter could ever want. The fact that he even uses the finest linens is impressive as many people get cheap with these things.  His homes offer a luxury vacation and convenience to everything. Disney is less than 3 miles away from his homes and you can get to just about everything you would need in less than 5 minutes.  The community itself has a movie theater, game room, water slide, convenience store and the list goes on. Windsor Hills has definitely raised the bar when it comes to vacation homes.  Because they are one of the newer communities in the vacation home niche, Pulte was able to see what worked and didn’t work in their previous communities and they made sure they got it all right the last time in Windsor Hills.

John’s vacation homes are a must stay in when visiting Orlando. Nothing has been overlooked and I think you’ll find his prices to be quite reasonable for a luxury resort.

Windsor Hills Resort Vacation Homes For Sale

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