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Highwood rentals with pool
We found 52 rentals with pool — enter your dates for availability
Explore Highwood rentals with pools

The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All!
Sleeps 99 · 3 bedrooms · 2+ bathrooms
Find spaces that suit your style
House
Condo/Apartment
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value