Find rentals with pool near The Skyline Trail

We found 2,971 rentals with pool — enter your dates for availability

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September 2025

October 2025

Explore The Skyline Trail rentals with pools

Premier Host

Waterfall House - Private House Overlooking the Ocean!

Sleeps 4 · 1 bedroom · 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

Premier Host

★Jump Start The Road to Hana at The Lookout House! Private Hot Tub + Pool Access

Sleeps 8 · 2 bedrooms · 2 bathrooms

Premier Host

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

Sleeps 6 · 2 bedrooms · 1 bathroom

Top rated rentals with pools - The Skyline Trail

Unsurpassed 180 degree views from our private rooftop lanai!

Premier Host

Maui Family Holiday

Great location, fantastic Penthouse, close to shops and across from the beach Couldn’t ask for a better place to stay

Ian C.

Stayed Sept 2023

Premier Host

Wonderful property couldn't ask for better

Thank you so much Mark for sharing your beautiful condo with us you couldn't ask for better everything you needed. Amazing beach at your door and swimming with the turtles every morning was a highlight for the children. We loved everything about Makena Surf and especially B-303. Hard coming back to New Zealand's cold and wet winter. Look forward to returning one day.

Sally M.

Stayed July 2016

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