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Kissimmee Vacation Rentals

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Management: Verified owner
Property: Rental Home
Bedrooms: 4, sleeps 10
Bathrooms: 3
Min stay:3
Stay at our very popular villa for 5 Star Luxury in the Sun! This large single story 4 bedroom, 3 bath Florida vacation home in Lindfields Estates is right ...
  • Nightly
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  • Weekly
    $809 - $975
  • Monthly
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Contact Owner
Nightly rate from
$89
Management: Verified owner
Property: Condo/Apartment
Bedrooms: 3, sleeps 8
Bathrooms: 2
Welcome to our beautiful three Bedroom, Two Bath Condominium, just a few miles from the Disney Properties, in the family paradise of Windsor Hills--the ...
  • Nightly
    $89 - $130
  • Weekly
    $623 - $875
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Contact Owner
Nightly rate from
$79
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 3, sleeps 8
Bathrooms: 2
FIVE OF THE MOST AMAZING HOMES IN DISNEY WORLD backed with a 100% money-back satisfaction guarantee! "How do you do it?" is the question we get most ...
  • Nightly
    $79 - $129
  • Weekly
    $553 - $903
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Management: Verified owner
Property: Rental Home
Bedrooms: 8, sleeps 16
Bathrooms: 9
This spectacular Villa is located at ‘The Estates Formosa Gardens’ Kissimmee, the closest community to Disney World. Formosa is renowned for its prestigious ...
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  • Weekly
    $4,950 - $6,500
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Contact Owner
Nightly rate from
$99
Management: Verified owner
Property: Rental Home
Bedrooms: 3, sleeps 6
Bathrooms: 3
Our beautifully furnished 3 bedroom townhome is located in the prestigious five-star gated resort community of Windsor Hills, just one mile (2 traffic ...
  • Nightly
    $99 - $119
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Contact Owner
Nightly rate from
$177
Management: Verified Plus owner
Property: Rental Home
Bedrooms: 5, sleeps 12
Bathrooms: 5
Closest to Disneyworld! DisneyDreamVilla is a luxury 5 bedroom / 5 bath private villa with screened pool and hot spa on an extended lanai. The villa ...
  • Nightly
    $177 - $275
  • Weekly
    $1,239 - $1,925
  • Monthly
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Contact Owner
Nightly rate from
$110
Management: Verified owner
Property: Rental Home
Bedrooms: 4, sleeps 8
Bathrooms: 3
A stunning Luxurious Vacationhome on the exclusive Bella Vida Resort. Under 6 miles from Disney and a few mins walk from Walmart. Restaraunts are all within a ...
  • Nightly
    $110 - $149
  • Weekly
    $730 - $1,040
  • Monthly
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Contact Owner
Nightly rate from
$150
Management: Verified Plus owner
Property: Rental Home
Bedrooms: 4, sleeps 10
Bathrooms: 2
Rent a pet friendly orlando vacation rental near Universal Studios or Disney World in the community of Indian Ridge Oaks in Kissimmee, Florida. You can now ...
  • Nightly
    $150
  • Weekly
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  • Monthly
    $3,500
Contact Owner
Nightly rate from
$115
Management: Verified Plus owner
Property: Rental Home
Bedrooms: 4, sleeps 10
Bathrooms: 3
Great home for traveling with another family or grandparents in one of the closest neighborhoods to Disney. Everyone will be comfortable with 2 master ...
  • Nightly
    $115 - $1,150
  • Weekly
    $165 - $1,200
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Contact Owner
Nightly rate from
$199
Management: Verified Plus owner
Property: Rental Home
Bedrooms: 6, sleeps 15
Bathrooms: 4
Gorgeous 6 Bedroom, 4 Bath home in the fabulous gated community of Windsor Hills less than 2 miles from Disney. This magnificent home sleeps 15 with 2 ...
  • Nightly
    $199 - $299
  • Weekly
    $1,393 - $2,093
  • Monthly
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Contact Owner
Nightly rate from
$69
Management: Verified owner
Property: Rental Home
Bedrooms: 3, sleeps 8
Bathrooms: 3
Located near the Disney theme parks this Kissimmee, Orlando, Florida vacation rental home is an ideal place to spend a luxury vacation. It is located in a ...
  • Nightly
    $69 - $89
  • Weekly
    $449 - $623
  • Monthly
    $1,500 - $1,700
Management: Verified owner
Property: Rental Home
Bedrooms: 7, sleeps 16
Bathrooms: 8
Min stay:7
This exquisite 7 bedroom plus den villa occupies a prime location in the prestigious Formosa Gardens Estates, directly on the lakefront with a south facing ...
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  • Weekly
    $5,200 - $6,800
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Contact Owner
Nightly rate from
$200
Management: Verified Plus owner
Property: Rental Home
Bedrooms: 5, sleeps 10
Bathrooms: 4
So close to Disney World you can almost touch it - Windsor Palms is the premier resort for the guest looking for all the excitement that the theme parks ...
  • Nightly
    $200
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  • Monthly
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Contact Owner
Nightly rate from
$200
Management: Verified Plus owner
Property: Rental Home
Bedrooms: 6, sleeps 12
Bathrooms: 4
Min stay:1
Welcome to our six bedroom, four bathroom, non-smoking, private vacation home in Windsor Hills Resort. You cannot find a closer resort community to Walt ...
  • Nightly
    $200 - $235
  • Weekly
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Management: Verified owner
Property: Rental Home
Bedrooms: 4, sleeps 10
Bathrooms: 2
Min stay:3
CALEDONIA is located just a few miles from Golf courses and Walt Disney World. Lots of family entertainment is available nearby, including Medieval Times ...
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  • Weekly
    $765 - $1,025
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Kissimmee Vacation Rental Advice
Posted by 1031Orlando, Nov 9, 2009
... as one of the best rental communities due ... ... if you really want a rental. You can get more space and keep the hotel/resort atmosphere by picking one the the vacation clubs or condo-hotels. Consider Hilton Vacation Club (SeaWorld or I Drive), Marriott Vacation Club (Grand Vista, Cyrpess Harbour ... more
Posted by CruisingtoRetirement, Jun 24, 2008
... I visited the Hilton Grand Vacations facility near Sea World today and was extremely impressed. It is my understanding that their two bedroom units are attached to stuido lockouts which makes three. There is a new facility under construction on Palm Parkway due to open in February that might also ... more
Posted by gammabean, Jul 2, 2009
... we will never rent a vacation villa from anyone in the Davenport/Orlando area again. We feel that staying at these remote vacation villas, especially ... ... we paid for our entire vacation; indeed it would have cost us less to arrange for the most deluxe accommodations at the Disney resort, an ... more
Posted by caylismom, Jul 17, 2009
... sorry for such an awful vacation experience!! We stayed at Solana twice. The first time was in 2005 when most of the resort was still being built. We had a good experience, although I really would not consider it a "resort", since there isn't much to do there, except ... more
Posted by Coralcaytownhome, Oct 2, 2007
... going to be renting. They also get to see all the photos of their actual rental home when booking direct with an owner. Some owners will also make small additions to their properties. Great to hear you like the townhomes on Coral Cay - the resort is in a great location ... more
Posted by toxKent, Oct 2, 2007
... pay for the actual townhouse rental (as no security deposit is required upfront). They also kindly upgraded us from the smallest townhouse floorplan to the largest anyway - as I said in the previous post, the resort was only 3% occupied (PEACE!) Please don't get me wrong, I am definately ... more
Posted by Coralcaytownhome, Mar 27, 2009
... indication of the whole resort - as this is not the case. There are many owners that are proud of their lovely homes and offer excellent customer service - we want our guests to have a really great vacation and take a personal interest rather than leave it solely to an agent ... more
Posted by theKteam, Sep 13, 2009
... are trying to find a vacation rental in ... ... nearer the Disney Parks area and miles away from downtown. Presuming that the downtown area is a decent place to stay in does anyone know a website where I can find vacation rentals specifically in this area? All advice gratefully received - thanks ... more
Posted by theKteam, Sep 14, 2009
... area if there are no rentals but wondered if you could suggest any other area (which is very near to downtown) where we might look for a vacation rental as another option? When I look at the rental sites it gets very confusing with all the names of the different ... more
Posted by CruisingtoRetirement, Sep 15, 2009
... area have changed ownership a couple of times recently and I am not sure of their current status. There is one very nice new building downtown with residences, but they are for full time residents and not available for rentals. Sorry, I wish I could give you better news. CTR ... more
Professionally managed typically means…
  • Member of the FlipKey Verified Property Manager program
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified Plus property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Verified property owner typically means…
  • Verification of owner name and address via valid credit card
  • History of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns