Leeward Coast rentals with pool

We found 2,334 rentals with pool — enter your dates for availability

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September 2025

October 2025

Explore Leeward Coast rentals with pools

GOLFERS DREAM - Located On The Famous Ko Olina #2 Fairway

Sleeps 6 · 3 bedrooms · 2+ bathrooms

Enjoy Breathtaking Views of the Ocean and Gorgeous Mountains!!! Newly Renovated!

Sleeps 3 · 1 bedroom · 1 bathroom

Top rated rentals with pools - Leeward Coast

Premier Host

Stunning

Bueatiful place right on beach with everything you need. stunning beach.

Kevin G.

Stayed Nov 2024

World Class Oceanfront Ko Olina Beach Villa Resort view from 7th floor lanai

Premier Host

Fantastic stay with perfect rooms for a family group

We travelled as a family group and the apartment was so well set up for us with each room very separate from each other and fantastic big bathrooms. The view was beautiful and the resort has such great pools for the whole family. We’d love to come back someday.

Gabrielle F.

Stayed Jan 2024

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