Hawaii Kai holiday rentals
We found 4,869 holiday rentals — enter your dates for availability
Discover a selection of 63 homes and other holiday rentals in Hawaii Kai that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the amenities that you need and want for your stay, which might include Wi-Fi and a washer and dryer. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Hawaii Kai
Showing deals for:17 Oct - 24 Oct
Image gallery for One free night with a 7 night booking. Great deals for Sept, Oct and Dec.

10 out of 10 rating
Exceptional
(11 reviews)
One free night with a 7 night booking. Great deals for Sept, Oct and Dec.
Waimanalo, HI
7% off
Price is S$39,306
S$5,615 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
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Find the best place to stay - Hawaii Kai
Showing deals for: 13 Oct - 16 Oct
Just What You Were Looking For! Sky View Unit with Kitchen, Outdoor Pool
Sleeps 4 · 1 bathroom
7.0 out of 10
good
(32 reviews)
The current price is S$893
for 3 nights, 1 home
S$298 per night
includes taxes & fees
Top rated rentals - Hawaii Kai

50th Anniversary Family Celebration
10 out of 10
exceptional
(108 reviews)
We chose Hawaii as our destination to celebrate our 50th Wedding Anniversary, with our children and grandchildren. From the moment we stepped through the welcoming front door, we knew we had chosen the perfect house for making lasting memories.
The living, family and dining rooms were spacious and bright, the kitchen was large and well equipped, with a well-stocked pantry and ample storage space for everyone’s favorite foods. The upstairs refrigerator provided plenty of space for leftovers as well.
The layout of the house was perfect for our family of 11, from the arrangement of the bedrooms to the open, easy floor plan which seamlessly accessed the outside spaces. We enjoyed gathering and eating on the spacious patio. The pool was enjoyed everyday by all, with plenty of pool floats and toys. We much appreciated the beach chairs, umbrellas, life vests, coolers and other necessities we found on hand for our trips to the beach.
The house is located in an attractive, quiet neighborhood, very convenient to shopping, dining, hiking and walks to the local beach, and within a short drive to many of the attractions that visitors to Hawaii come to experience.
Donna was a very welcoming and gracious host, and was available to answer all of our questions, and to provide us with information about the local area. We feel that we could not have picked a better location or house for our family celebration. Everyone from the 5 year old to the two 70’s enjoyed everything this house had to offer. We feel blessed to have had this experience.
A big mahalo to Donna!
John F.
Stayed Jun 2022
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value