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5 Kissimmee Resort Communities We Know You’ll Love!

We’ve hand selected these 5 fabulous vacation home Kissimmee resort communities that we know you’ll love. Whether you’re buying or just renting for a week these resorts will not let you down.

Kissimmee Resort Communities


Kissimmee Resort #1

Windsor Hills Resort

Clubhouse at Windsor Hills Resort

Clubhouse at Windsor Hills Resort

The Windsor Hills Resort offers something for everybody. Single family, townhouses and condos are all available in this Kissimmee Resort. If you’re looking to invest in a vacation rental and want something that is going to generate you an income after your expenses are paid, the Windsor Hills Kissimmme Resort is one of your best choices. Our owners in this Kissimmee Resort are currently seeing a positive cash flow every month on their financial statement. Some are having such great success that they keep going back to buy more homes in the Windsor Hills Resort, but why is Windsor such a money maker? Easy, the Windsor Hills Resort has a loyal client base of guests who come back each year. With most of the largest management companies focusing mainly on the Windsor Hills Resort the community is exposed to a huge group of people every month.

Check Out All The Homes For Sale in the Windsor Hills Resort Here! 

Photos of the Windsor Hills Resort in Kissimmee


Kissimmee Resort #2

Paradise Palms Resort

IMG_9814The Paradise Palms Resort was Lennar’s way of one upping all of the existing vacation rental resorts that were already completed during the boom. Single family & townhomes are available in this Kissimmee Resort. If you’re looking to invest in a vacation rental that has the newest and most sought after toys than look no further, the Paradise Palms Kissimmme Resort is one of the best options. The Paradise Palms Kissimmee resort was designed to be unique in the market. It has one of the nicest and most impressive clubhouses in the Kissimmee area, it’s only rivaled by a handful of newer resorts that were designed to one up this resort community. 

Check Out All The Homes For Sale in the Paradise Palms Resort Here! 

Photos of the Paradise Palms Resort

Kissimmee Resort # 3

Encantada Resort 

Encantada Resort KissimmeeThe Encantada resort is located in such a great spot right off the highway 192. It’s close to the 429 making it easily accessible to get just about everywhere in Orlando. Beyond it’s location it also offers visually appealing and spacious townhouses with private patios that all have in ground hot tubs and the end units have splash pools. The Kissimmee resort itself has two swimming pools and all the amenities you would expect at a five star resort. What makes the Encantada Resort such a great buy for a vacation home shoppers is that the prices are very fair for what you get and the rental rates continue to stay higher compared to other Kissimmee townhouse communities. This could be because half of the community is owned by a timeshare company and the other half are all privately owned by investors but whatever the reason, the Encantada townhomes remain a good buy even going into 2016.

Check Out All The Homes For Sale in the Encantada Resort Here! 

Kissimmee Resort #4

Oakwater Resort

Oakwater Resort PoolThe Oakwater Resort is one of the simplest decisions you’ll ever make. Location + Amenities= Cash Flow. With the prices being so affordable and the location being one of the closest privately owned resorts to Disney this resort is a MUST SEE when you come to Florida to shop for a vacation rental. The Oakwater resort is a condo community but it doesn’t feel like one. It has garages and open floorplans so they actually feel more like a townhouse when you’re in them. The location will also rock your world if you’re owning here because of Disney. It’s literally right up the street from the Disney entrance and is without a doubt one of the most booked Kissimmee Resorts by travel agencies and management companies. 

Search all Oakwater Resort Condos For Sale Here

Photos of the Oakwater Resort in Kissimmee

Kissimmee Resort #5

Windsor Palms Resort

This Kissimmee Resort makes our list because, like a well oiled machine, it keeps working and standing the test of time. The Windsor The_Best_Kissimmee_Specialty_Lodging_-_TripAdvisor 8Palms resort is the sister resort to Windsor Hills and it was the first resort to be built out of the two. It has the “Windsor” brand recognition behind it and a very loyal database of clients who stay only here and Windsor Hills every year. If you’re looking for something reliable, tried and true than you can’t go wrong with the Windsor Palms resort (formerly Wyndham Palms). It was even in Tripadvisor’s top 10 specialty resorts for 2016 when sorted by ranking. If that’s not validation enough, we don’t know what is! 

Search all homes for sale in the Windsor Palms Resort Here

Photos of the Windsor Palms Resort Kissimmee

We hope to earn the opportunity of helping you achieve your  vacation rental investment property goals this year. For a free, no obligation investment property consultation with us,  please contact us directly at 866-422-6191 and if you have enjoyed this article please consider subscribing to our blog and stay updated on future information.



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