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VRBO is part of the HomeAway family, the world leader in vacation rentals with over 950,000 listings. We offer the largest selection of properties for any travel occasion and every budget. We’re committed to helping families and friends find a perfect vacation rental to create unforgettable travel experiences together. Learn More

Windward Cay - 17 vacation rentals

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This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation

Windward Cay Travel Tips

Windward Cay Kissimmee Vacation Rentals by Owner

Kissimmee villas in the Windward Cay community are just 10 minutes from Disney, 15 minutes from Sea World Orlando, and accessible to Orlando restaurants and entertainment. You’ll love having your own private retreat at Windward Cay Kissimmee houses with lots of room for you to relax with family and friends inside or outside by the pool - many Kissimmee vacation rental houses have private swimming pools. Plan your Disney vacation and find a luxury rental house in Windward Cay Kissimmee on VRBO.

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