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Private pool at our Encore Club vacation rental

Move over tiny studio apartments and awkward key exchanges with home owners there’s a better game in town when it comes to vacation rentals for travellers, especially if that town is Kissimmee, Florida.

Kissimmee is one of those places that is known more for its proximity to other attractions in Florida than for its own, and that’s okay. In fact, Kissimmee touts the fact that it is a stone’s throw from Orlando’s theme parks, an hour’s drive from either coast, and close to plenty of outdoor activities and adventures. Which makes it the ideal place to base yourself if you are planning a visit to central Florida and want a more cost-effective option for lodging than those pricey themed resort hotels. (you know the ones I’m talking about!)

A Kissimmee Vacation Rental Property for Everyone

One of the best options if you are travelling with a group, or even just another couple, is to look at staying in one of Kissimmee’s vacation rental properties ? of which there are literally thousands! I had no idea that these kinds of communities even existed, where entire ‘subdivisions’ of private homes are constructed on resort-like properties, but when not in use by their owners, are rented out to visitors. These homes run the gamut from 2-bedroom condos to detached homes to enormous luxury mansions (one even has its own bowling alley and Turkish bath!).


This luxurious mansion offers its own bowling alley, Turkish Spa, games room and more! *Photo Jeeves website

But unlike most of the AirBnBs in the world, the rental process is looked after by property management companies who take care of all the details for both the owners and the visitors. One of these companies is Jeeves Florida Rentals.

“Thank you, Jeeves!”

On a recent visit to Kissimmee this November, I stayed with 5 other guests in one of the Encore Club properties managed by Jeeves Florida Rentals, and like the name suggests, Jeeves provided the kind of ‘butler service’ you typically only get at high-end resorts. Because in addition to making sure our home was equipped with everything we needed right down to a bottle opener, Jeeves can provide a range of other services to make your stay feel like the vacation it should.

What kind of services does Jeeves offer?

Jeeves can arrange everything from grocery delivery, to ticket sourcing, to transportation assistance, to the services of a private chef who will come to your home and prepare a meal for the entire group. We were actually treated to a dinner prepared by Elijah Durham, Executive Chef at Elemental Chef Inc, who came to our home, served a delicious meal, and even packaged up the leftovers for us to enjoy the next day.


Chef Elijah Durham of Elemental Chef Inc.


Bruschetta appetizers prepared for us by Chef Elijah

Deluxe Accommodations


Great room with one of 10 TVs in the house

The property itself is key to the experience, of course, and our particular home offered a large great room for lounging, cooking and dining, and 8 bedrooms (most with ensuite or private baths and each with their own TV).


One of 8 bedrooms and baths, all tastefully decorated, spacious and comfy

There was a pool table on the second floor, and a media room with stadium-style seating, a giant Netflix-enabled giant TV and even a PlayStation for any guests who may be avid gamers.


The media room came equipped with Netflix and stadium seating

And of course, a private pool meant there was no need to even leave the property if we wanted to go for a dip, although Encore Club also has its own full-on water slide as part of its central resort-like pool complex. (There’s also a bar, gym, tennis courts and games room here, all available free of charge!)


Encore Club offers resort-like amenities including a water slide, all of which are free for guests. *Photo Jeeves website

Luxury for Less


Nothing says ‘Welcome Home!’ like a glass of Pinot Grigio chilled in your own gourmet kitchen!

If this all seems to good to be true, this ought to seal the deal: all this space, and all these amenities came at a really reasonable price: $360/night. That’s per night, not per person, for the entire house. I’ll leave it to you to do the math, because even if you only fill half of the 8 bedrooms, this is a steal for this calibre of accommodation.

I’m a big fan of accommodations that make me feel ‘at home’ when I’m travelling, so if you are one of these people too, and are thinking of heading south to the Orlando area, check out a vacation rental in Kissimmee. Based on my experience with Jeeves, they do it right.

Special thanks to Experience Kissimmee, and Jeeves Florida Rentals, who hosted me during my visit to Florida and showed me how to do vacation rentals right.

Jane with Hat Tanzania

Jane Canapini is a member of the Travel Media Association of Canada and the North American Travel Journalists Association. She established in 2014 to share information and tips based on personal experience so her readers could get the most out of their travels.

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