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Windsor Park family rentals

We found 20 family rentals — enter your dates for availability

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September 2025

13

October 2025

Find the best place to stay - Windsor Park

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NEW “Sunset Cottage”minutes to beaches and more!

Sleeps 4 · 1 bedroom · 1 bathroom

Steps to downtown, short walk to waterfront, beaches close by. Your spacious and private getaway awaits.

No Hurricane Damage Walk to Downtown Dunedin and Waterfront Private Home for 8

Sleeps 8 · 3 bedrooms · 2+ bathrooms

Find spaces that suit your style

Holiday Rental options in Windsor Park

Holiday rentals with pool in Windsor Park

Ski holiday rentals in Windsor Park

Holiday rentals with spa pool in Windsor Park

Lake holiday rentals in Windsor Park

Mountain holiday rentals in Windsor Park

Pet-friendly holiday rentals in Windsor Park

Beach holiday rentals in Windsor Park

Oceanfront holiday rentals in Windsor Park

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