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Post Updated for 2016

I like Kissimmee gated communities, I like them because they do a good job of keeping solicitors away and even though people can still get in, they just have the effect of making me feel safe at night.  This post is The Flamingo Ode to the best Kissimmee gated communities near Disney.  I hope you find it helpful in your search for an Orlando vacation home property.

BellaVida ResortBELLAVIDA_RESORT_CSS_7_420X3902The BellaVida resort is one of the Kissimmee gated communities that really stands out. It’s every bit as lovely as its Italian name.  What it lacks in amenities it makes up for in architecture, charm and location.  BellaVida resort vacation homes are walking distance to shops, right up the street from Wal-Mart and have a unique Tuscan charm.  The Bellavida resort is comprised of townhouses and single family villas.  There are still some brand new homes left and we do offer an exclusive $10,000 closing cost credit on any new purchase (check here for details)!! The Bellavida resort offers townhomes and single family villas, all beautiful in their own unique way. This community was developed by Park Square and is a very popular vacation rental destination for travelers from all over the world. This Kissimmee gated community is better suited for vacation rental owners than full time residence because of how transient it is.

BellaVida Homes For Sale

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Emerald_Island_resortEmerald Island Resort: If you’re the kind of person who wants it all and wants it all for a good price than Emerald Island is going to be one of your favorite Kissimmee gated communities.  The Emerald Island Resort features a Community Heated Pool, Fitness Center, Parks, Tiki Bar and Rec Building.  The gate is manned and the entrance makes you feel like your at a world class resort, not a Kissimmee Residential Neighborhood.  The community is comprised of Single Family Homes and Townhomes ranging from the mid $100,000 to over $500,000. There are two community pools, one for the townhouse section and one main one for the Single Family Villa section. The location is also fabulous, it’s right in the popular Formosa Gardens area which is basically the center of everything in the Kissimmee resort area.

Check out all the Emerald Island Homes For Sale

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Encantada Resort KissimmeeEncantada: Bring your tennis racquets because this is one of the Kissimmee gated Communities that has lots to do on site! The Encantada resort community is sure to be a vacation home you’ll enjoy for years to come with a guarded gate entrance, exotic community pools and clubhouse.  The architecture and colors will make you feel like your in the Caribbean somewhere (not to mention all the beautiful bougenvillas that are planted all around) and the prices of these town homes will make your jaw drop. Compared to all the local new construction going up, these are a huge bargain!  Did I mention that some of the Encantada townhomes even have their own private pools with screened enclosures? There are tons of great deals to be had in this Kissimmee Gated community. You can search all of the Encantada townhomes for Sale here.

Read Also: 4 Kissimmee Resort Communities with Private Waterparks


Kissimmee Gated CommunitiesWindsor at Westside: Windsor at Westside is one of the newest Kissimmee gated communities to enter the vacation rental market. Pulte started construction just over a year ago and it’s already proving to be one of the most sought after vacation rental neighborhoods in the West Kissimmee area. There is a manned gate however until the community is closer to completion there won’t be a guard in there full time. The community boasts a beautiful private waterpark with it’s very own lazy river, water playground, onsite restaurant and resort clubhouse. There is also a beautiful lake in the center of the community with a dock. The Windsor at Westside resort offers single family and townhouses. We are currently offering a very exclusive closing cost credit of $10,000 to help pay for your closing expenses on any new home. Check out the details here.

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Encore at ReunionEncore Club at Reunion: Stop and drop everything you’re doing right now, you’ve just landed on one of the most fabulous Kissimmee gated communities in Orlando. I could spend days going on about how incredible this resort is but somehow I have to figure out how to do this in a few sentences. Lets start with the water park. It’s insane. It has three enormous water slides and an epic pool. It also has a gorgeous clubhouse with an onsite restaurant. There is also additional restaurants, golf courses and pools on the Reunion side that you can access. Here is the kicker, Encore is being built in two phases. The side that is next to the clubhouse and the side that is across the street. The better side is the one that is next to the clubhouse but they are selling out quick. It’s a new community (the Encore side, Reunion has been around for a while) so we’re offering an exclusive $10,000 cash rebate towards your closing costs on any new purchase!

Read Also: The Chuck Norris Guide To Closing On Your Vacation Rental in 30 Days or Less


Kissimmee Gated COmmunitiesParadise Palms ResortIf you like Encantada, Windsor at Westside & Encore than you will LOVE the Paradise Palms Resort in Kissimmee.  Though not for the budget conscious it’s definitely a real estate investment that you won’t regret making in the years ahead.  The community is comprised of both townhouses and single family villas. The townhouses are more like attached single family homes as the size of them is larger than many of the detached pool villas in Kissimmee and Davenport.  Every home has it’s own private pools and the community amenity list rivals that of Regal Palms and Windsor Hills.  This is one of the few Kissimmee Gated Communities that is designed for both the young kids and adults alike. The clubhouse has a movie theater and a convenience store as well as an arcade. The pool has a grotto!  Somebody stop me before I go buy one. . . Check out all the Paradise Palms Homes For Sale Here.

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Kissimmee gated communitiesLake Berkley Resort: As far as Kissimmee gated communities go this one is definitely different than all of the rest. It does have a guard gate and the security there is some of the strictest in the area. Good luck trying to get through there without your blood type!! The reason it’s different is because the homes are much older, they’re built more like a residential community and it doesn’t have that over the top resort feel. There’s not a ton of amenities like some of the Kissimmee gated communities mentioned above however, it’s very peaceful there. The Lake Berkley resort has a beautiful lake and dock in the community. The homes have bigger lots than the newer communities and you’re more likely to find private backyards there which is important to many people looking to invest in a vacation rental. If you’re that person who’s looking for privacy, nature and a little splash of a resort than this would be an incredible choice for you. The Lake Berkley resort has both townhouses and single family villas.

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Windsor Hills Entrance Kisismmee, FLWindsor Hills: Whether you are looking for a condo, townhouse or single family home (all three of these links will take you to the current homes for sale) this is one of the Kissimmee gated communities you can find it in. The Windsor Hills resort is a lovely gated community that is only 2 miles to Disney, so technically you could ride your bike there to avoid parking fees (that was a joke but I am sure there are people who would do it). It’s also one of the closed private vacation rental resorts to Disney. Windsor Hills is considered the Buckingham Palace of Kissimmee, it has a humongous following of guests who come back every year, especially from the UK.  The homes are absolutely gorgeous, spacious and grand and you will get what you pay for.  If the name sounds familiar it’s probably because we just talked about the sister community, Windsor at Westside, above. That community spawned off this one. It was having so much success that Pulte went ahead and did it again. You will pay close  to the top of market value for a vacation rental in here but you will also generate top rental income to it balances out. We know many owners in here who own multiple homes and keep buying more.

Read Also- Through the Eyes of a Windsor Hills Vacation Rental Buyer


OOakwater Resort Poolakwater ResortAfter updating this for 2016 I actually took out the Windsor Palms Resort and put this one here instead. Why did I do that? Well it’s simple, even though Windsor Palms was a great choice, it’s started to get dated. The Oakwater Resort is also the closest private vacation rental resort to Disney. You simply can’t get closer to Disney unless you stay onsite at Disney. The location is absolutely fabulous. I also wanted to put something in here for those of you looking for a condo. Even those these are condos they are definitely not short on amenities or space. The resort is incredibly well maintained and continues to stay booked throughout the year. Most likely due to it’s awesome location and amenities! If a condo is what you’re seeking than this is one of the best Kissimmee gated communities to find that in. The prices are also very reasonable.

Check out what’s for sale in the Oakwater Resort here.

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We hope to earn the opportunity of helping you achieve your investment property goals this year. To set up a free, no obligation investment property consultation with us please use our scheduling tool or 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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