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The 9 Best Kissimmee Gated Communities to Own a Vacation Home In

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I like 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.



The BellaVida resort in Kissimmee, FL is every bit as lovely as its Italian name.  What it lacks in amenities it makes up for in architecture, charm and location.  BellaVida vacation homes are walking distance to shops and have a unique Tuscan charm.  Bella Vida is comprised of townhouses and single family villas.  Many of the homes are brand new and also over priced however, there are some bank owned townhomes and villas in BellaVida that make it a worthy option for your Kissimmee vacation home purchase.

BellaVida Homes For Sale

Emerald Island Resort


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If you’re the kind of person who wants it all and wants it all for a good price than Emerald Island is the place for you.  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 $120,000 to over $500,000.

Emerald Island Homes For Sale


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Bring your tennis racquets to Encanda in Kissimmee.  The Encantada community is sure to be a vacation home you’ll enjoy for years to come with a guarded gate entrance, exotic community pool and clubhouse.  The architecture and colors will make you feel like your in the Caribbean somewhere and the prices of these town homes will make you feel like you just walked into a Wal-Mart rollback special.  Did I mention that some of the Encantada townhomes even have their own private pools with screened enclosures? Encantada has bank owned townhomes starting barely over $100,000.

Encantada Homes for Sale

Formosa Gardens


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Formosa gardens in Kissimmee, FL is a community unlike the rest.  These estate homes have yards and they are not packed in like sardine cans.  The community is an upscale neighborhood and is reflected in the prices of the homes.  Is Formosa Gardens right for you? Can you justify the price for the return on bookings?  My answer to these common Formosa Gardens real estate questions is simple. . . probably not.  The return you get on the bookings will be a bit higher than many of the other short term rental communities however, it’s not going to be anywhere close to where it needs to be to justify the price.  In my honest opinion, Formosa Gardens is perfect for the homeowner who wants to live there full time or the high end corporation who rents only estate style homes to celebrities and luxury travelers.  Formosa Gardens is not a smart investment for the average vacation home buyer who wants a  good deal for a good price.

Formosa Gardens Homes For Sale

Legacy Dunes Condos


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If your looking for Kissimmee condos under $50,000 you’ve come to the right place.  Legacy Dunes Condos in Kissimmee are not only the best value but the quality and amenities you get for the price of these condos will blow you away.  The Legacy Dunes Community features: Two Pools, Clubhouse, Fitness Center, Business Center, Game Room, Tiki Bar, Tots Playground, Barbeque Area, Gazebo, Tennis Courts, Basketball Courts, Golf Driving Practice Net, Lakes & Conservation Areas, Covered Parking Garages, Two Car Washing Facilities and Two Laundry Facilities.  Did I mention the condos are starting at $24,000?  Why buy a new car when you can invest in one of these Kissimmee vacation home bad boys!

Legacy Dunes Condos For Sale

Paradise Palms Resort


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If you like Encantada 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 all townhouses but they 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.  The townhomes have their own private pools and the community amenity list rivals that of Regal Palms and Reunion.  My favorite thing about Paradise Palms is their tot lot splash park.  I love the fact that the children are not forgotten in this community and did I mention the gorgeous interiors and furniture packages?  Somebody stop me before I go buy one. . .

Paradise Palms Townhouses For Sale

Sunset Lakes


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I can’t believe I am actually going to say this but here it goes, “Location, Location, Location!” It’s true about Sunset Lakes in Kissimmee, FL.  This single family home gated community is so centrally located to Disney it should be a part of the resort!  Aside from it’s perfect location it makes my list for the reason that it’s tried and true.  Sunset Lakes Homes have been going strong with bookings for over 10 years now.  They are a solid investment for the short term vacation home buyer and the price range is reasonable.  There are bank owned properties for sale in Sunset Lakes right now so you can pick up a deal. You can also pick up homes in Sunset Lakes that have transferrable bookings for 2009.

Sunset Lakes Homes For Sale

Windsor Hills


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Whether you are looking for a condo, townhouse or single family home Windsor Hills in Kissimmee has it.  This lovely gated community 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 will do it).  Windsor Hills is considered the Buckingham Palace of Kissimmee.  The homes are absolutely gorgeous, spacious and grand and you will get what you pay for.  Speaking of what you pay for, prices for Windsor Hills Pool Villas start in the low 300′s.  That’s a small price to pay for a Windsor Hills address.

Windsor Hills Homes For Sale

Windsor Palms
(formerly Wyndham Palms)

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Think of Windsor Palms in Kissimmee as the competitive big sister to Windsor Hills.  Located just on the opposite end of 429 Windsor Palms is much smaller than Windsor Hills but is very comparable in every way.  Windsor Palms offers Condos, Townhouses and Single Family Homes and the villa layouts are perfect for short term rental use.  Many have double master suites and some of the larger houses go up to 6 bedrooms for maximum booking potential.

Winsdsor Palms Homes For Sale

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