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Vacation homes in Kissimmee, Florida

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
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Verified 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
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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$166
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
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$219
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5 Bedrooms, 5 Bathrooms, Sleeps 12
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$160
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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Also consider
Gorgeous 4 BDR/ 3BA Pool home, Themed Rooms
4 Bedrooms, sleeps 8
$160 / night
4 Bedroom On Lake View Plot at VillaSol
4 Bedrooms, sleeps 10
$123 - $153 / night
Brand New Executive Quality Home!
6 Bedrooms, sleeps 14
$1,226 - $1,652 / week
' The Artist House ' Only 3 Miles from Walt Disney
4 Bedrooms, sleeps 8
$970 - $1,007 / week
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$282
Per Night
5 Bedrooms, 5 Bathrooms, Sleeps 10
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$320
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5 Bedrooms, 5 Bathrooms, Sleeps 10
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$305
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6 Bedrooms, 4 Bathrooms, Sleeps 14
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$174
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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$193
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
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From
$160
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
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$120
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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$319
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 15
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$532
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6 Bedrooms, 4 Bathrooms, Sleeps 12
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$532
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6 Bedrooms, 4 Bathrooms, Sleeps 12
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$156
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
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$319
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 12
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$194
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 10
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$304
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6 Bedrooms, 5 Bathrooms, Sleeps 12
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$161
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3 Bedrooms, 3 Bathrooms, Sleeps 8
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$369
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 12
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$466
Per Night
5 Bedrooms, 5 Bathrooms, Sleeps 10
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$296
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6 Bedrooms, 5 Bathrooms, Sleeps 14
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$123
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3 Bedrooms, 3 Bathrooms, Sleeps 8
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$245
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5 Bedrooms, 5 Bathrooms, Sleeps 10
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$336
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 10
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$155
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$160
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$185
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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$384
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5 Bedrooms, 5 Bathrooms, Sleeps 10
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$226
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7 Bedrooms, 4 Bathrooms, Sleeps 14
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$330
Per Night
5 Bedrooms, 5 Bathrooms, Sleeps 10
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From
$225
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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From
$288
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 10
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From
$145
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$225
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5 Bedrooms, 5 Bathrooms, Sleeps 11
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From
$321
Per Night
5 Bedrooms, 5 Bathrooms, Sleeps 10
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From
$548
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 12
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From
$117
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
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From
$147
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 10
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From
$208
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 12
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From
$1,066
Per Night
9 Bedrooms, 12 Bathrooms, Sleeps 24
39 photos Details
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Suitability

  • Wheelchair access (533)
  • Elder access (1,505)
  • Suitable for children (2,217)
  • Pet friendly (141)
  • Smoking allowed (5)

Amenities

  • Internet (2,493)
  • Air Conditioning (2,468)
  • All pools (2,215)
  • Other outdoor space (1,599)
  • Washer/Dryer (1,534)
  • View all amenities
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Kissimmee Vacation Rentals

Don’t automatically think you need to rent a vacation home in Orlando to be close to Walt Disney World. Smart vacationers know that searching for a vacation rental in Kissimmee, Florida often gets you space, luxury and a great rate—as well as a very short commute to the parks.

Kissimmee Vacation Rentals for Families

More and more families are choosing to celebrate major events like birthdays and anniversaries with a multi-generational trip to Disney World. (It’s one of the few destinations where everyone from toddlers to seniors can have an equally great time.) And we can help you find a Kissimmee vacation rental that can handle any size family. Whether you’re interested in a one-bedroom condo rental in Kissimmee or a seven-bedroom luxury villa, our helpful vacation rental reviews make your selection easy.

Advantages of renting a vacation home in Kissimmee

Let’s be honest—while it’s great fun to spend a week visiting the Magic Kingdom, Epcot, Disney’s MGM Studios, Universal Studios and Islands of Adventure, for most of us, it’s a significant strain on our bank accounts. Staying in a hotel and eating in Orlando-area restaurants also adds up. However, we can help you find a great deal on a villa rental in Kissimmee… and even if you just take a few meals in your vacation home instead of in restaurants, your budget will thank you. You’ll even save money on baggage fees with a rental—when you’ve got your own washer and dryer, you can do a few loads of laundry and pack much less clothing.

Rent a vacation house with a pool in Kissimmee, Florida

How do you visit the Orlando theme parks and maintain your sanity? Escape the crowds in the mid-afternoon, when the heat peaks and everybody’s nerves are frazzled. By staying just a short distance away in Kissimmee, you can zip home for a refreshing dip in the pool. Little kids can nap in the comfortable A/C of your Kissimmee vacation rental. You’ll all return to WDW or Universal in a much better mood!

Rental deals in Kissimmee

Remember that Florida’s a year-round vacation destination—but it definitely has an off-season when you can snag a great deal on Kissimmee condo rentals. If you really want a bargain, plan to visit Kissimmee between Thanksgiving and Christmas. Your condo will be cheap, the parks will be less crowded, and if you’re coming from a northern climate, the weather in Kissimmee will still seem great compared to what you’d get at home.

Kissimmee and Orlando beyond Disney

Don’t forget, there’s more to this part of Florida than Mickey and Donald and friends. Animal lovers will want to spend a day at Sea World, or take a day trip to the Everglades. Shoppers should save time (and suitcase space) for bargain-hunting at outlets in Kissimmee and the nearby Orlando Premium Outlets. Just over an hour away, on Florida’s Space Coast, you’ll find the Kennedy Space Center and fantastic sandy beaches like Cocoa Beach. Taking a Disney Cruise departing from Port Canaveral? A vacation rental in Kissimmee is the perfect pre-cruise accommodation.