The Cliffs holiday rentals

We found 103 holiday rentals — enter your dates for availability

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February 2026

March 2026

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Find the best place to stay - The Cliffs

Premier Host

Cliffs at Princeville #3201, Beautiful Ocean-Bluff Resort, Private Lanai

Sleeps 4 · 1 bedroom · 2 bathrooms

Fantastic Oceanfront Condo at the Cliffs Resort. Great amenities & free WiFi.

1 bedroom · 2 bathrooms

Premier Host

The Cliffs at Princeville #7302, Pristine Ocean-Bluff Views, Private Lanai

2 bedrooms · 2 bathrooms

Top rated rentals - The Cliffs

Image of Very Private location. Amazing View. The Cliffs 6302, 1 Vehicle Parking Included

Premier Host

40th Anniversary

Great location and terrific hosts (both communication and property). Lovely tropical flower centerpiece welcomed us and the Concierge services were very helpful . Pool/ Bike rental were nice as well. Access to a local grocery store was a plus. Fitness center could use more space. Will definitely consider staying at the Cliffs in the future and at this unit.

Michael K.

Stayed Oct 2021

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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