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Leeward Settlement cottage rentals

We found 6 cottage rentals — enter your dates for availability

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value
Holiday Rental options in Leeward Settlement
Oceanfront holiday rentals in Leeward Settlement
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Family-friendly holiday rentals in Leeward Settlement
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Ski holiday rentals in Leeward Settlement
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Beach holiday rentals in Leeward Settlement
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Holiday rentals with pool in Leeward Settlement
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Pet-friendly holiday rentals in Leeward Settlement
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Mountain holiday rentals in Leeward Settlement
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Monthly rentals in Leeward Settlement
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Holiday rentals with spa pool in Leeward Settlement
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Lake holiday rentals in Leeward Settlement
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