Kailua rentals with pool

We found 32 rentals with pool — enter your dates for availability

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September 2025

October 2025

Explore Kailua rentals with pools

Enjoy the natural lighting from the large glass windows.

Premier Host

Serene Eco Retreat: Ocean Views, Waterfalls, and Scenic Trails!

Sleeps 2 · 1 bedroom · 1 bathroom

Premier Host

HAWAIIAN DREAM TEMPLE - w/Private Hot Tub and Shared Pool - Permit#BBPH2012-0004

Sleeps 6 · 2 bedrooms · 1 bathroom

Entrance to the Cliff House through the private garden and pool.

Premier Host

Cliff House - Stunning Private Home with Ocean View and Pool and Spa

Sleeps 4 · 1 bedroom · 1 bathroom

So many of our guests have commented that they love the feeling of "coming home"

Premier Host

★Star Honeymoon Lookout - PRIVATE HOT TUB + ACCESS TO POOL + New Central AC✔

Sleeps 4 · 1 bedroom · 1 bathroom

Top rated rentals with pools - Kailua

Premier Host

Beautiful views and lovely property

This property is lovely and tucked away amongst green Hawaiian forest. Easy a quick access from Hana Hwy. Clean house with great facilities. Breakfast provided in the morning is a great touch. Would definitely stay again.

Tim B.

Stayed July 2023

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