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Vacation Rentals in Windsor Hills Resort, Kissimmee

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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

DEAL!! Luxury New 6BR/Pool/Spa/Lanai/Game villa, 1.5Mile to Disney
Kissimmee Villa Rental Picture
  • Villa Rental Deals and Discounts $30 off = $170 per night
  • bedrooms 6
  • community Windsor Hills Resort
  • rental type Villa
  • sleeps 13
  • baths 4
  • rates (USD) $160 - $285 /nt
    $1,120 - $1,995 /wk
 
 
 
 
 

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Windsor Hills Pool View Condo - Windsor Hills resort
Kissimmee Condo Rental Picture
  • bedrooms 3
  • community Windsor Hills Resort
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $79 - $169 /nt
 
 
 
 
 

118 reviews write a review

Executive Home - Pool - Close to Disney
Kissimmee House Rental Picture
  • bedrooms 6
  • community Windsor Hills Resort
  • rental type House
  • owner badgeowner badge
  • sleeps 14
  • baths 4
  • rates (USD) $200 - $250 /nt
    $1,400 - $1,750 /wk
 
 
 
 
 

50 reviews write a review

5 Star Resort- Closest to Disney
Kissimmee Townhome Rental Picture
  • bedrooms 3
  • community Windsor Hills Resort
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $125 - $149 /nt
    $875 - $1,043 /wk
    $3,750 /mth
 
 
 
 
 

69 reviews write a review

Luxury Villa Windsor Hills 3 miles to Disney S. Facing pool
Kissimmee House Rental Picture
  • bedrooms 6
  • community Windsor Hills Resort
  • rental type House
  • owner badgeowner badge
  • sleeps 14
  • baths 4
  • rates (USD) $180 - $300 /nt
    $1,295 - $2,450 /wk
    $3,999 - $5,999 /mth
 
 
 
 
 

15 reviews write a review

Windsor Hills Luxury Condos Close to Disney
Kissimmee Condo Rental Picture
  • bedrooms 3
  • community Windsor Hills Resort
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $39 - $135 /nt
    $273 - $945 /wk
 
 
 
 
 

26 reviews write a review

Windsor Hills Condo 3 bed w/lake view April 2014 - $95. NT
Kissimmee Condo Rental Picture
  • bedrooms 3
  • community Windsor Hills Resort
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $90 - $135 /nt
    $650 - $800 /wk
 
 
 
 
 

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New Windsor Hills Resort~Perfect for families!
Kissimmee House Rental Picture
  • bedrooms 3
  • community Windsor Hills Resort
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $575 - $750 /wk
 
 
 
 
 

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Fall Special, Up to 20% off! Luxury 3/2 Condo
Kissimmee Condo Rental Picture
  • bedrooms 3
  • community Windsor Hills Resort
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $89 - $155 /nt
    $623 - $1,085 /wk
 
 
 
 
 

4 reviews write a review

Exceptional Pool Home 2 Miles to Disney, Game Room, Internet
Kissimmee House Rental Picture
  • bedrooms 6
  • community Windsor Hills Resort
  • rental type House
  • sleeps 15
  • baths 4
  • rates (USD) $199 - $369 /nt
    $1,400 - $2,100 /wk
    $5,000 - $6,000 /mth
 
 
 
 
 

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