Kailua family rentals

We found 92 family rentals — enter your dates for availability

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September 2025

October 2025

Find the best place to stay - Kailua

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

Premier Host

Maui Plantation Cottage Located Near Beach And Paia, Permitted Bbph 2017/0004

Sleeps 6 · 2 bedrooms · 2 bathrooms

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

Top rated rentals - Kailua

Premier Host

delightful quiet location

Lovely room and communal kitchen with views over the garden to the ocean. It was a good base from which to explore Maui

Veronica W.

Stayed Aug 2024

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

Premier Host

Maui North Shore Hidden Treasure

Excellent base for exploring and enjoying all that Maui has to offer. Fully equiped, very comfortable and high quality. Super helpful and friendly hosts. I would recommend this cottage to anyone wanting a great location and quality on the Maui North Shore.

Ruth G.

Stayed July 2019

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