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Holiday rentals near Kaupo Bay
We found 492 holiday rentals — enter your dates for availability
Find the perfect holiday home that's near Kaupo Bay. Holiday homes provide the amenities that you need and want for your family, friends or furry companion, such as parking and a washer and dryer. Whatever you're looking for, you'll be able to choose a property to rent that has what everyone needs, including accessible or non-smoking choices.
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Top rated rentals - Kaupo Bay

Perfect
10 out of 10
exceptional
(138 reviews)
This was the perfect property and place for us to begin our Hawaiian stay. We moved away from Kailua six years ago and it was our first visit back. The view of Kailua beach and the ocean from the room's window is gorgeous. Waking to the sound of the waves crashing is wonderful. The unit was immaculate. The bed was very comfy, and the shower was also very good. Communication with the owner, Shari, is excellent. We highly recommend this beautiful little slice of heaven on earth. Aloha.
Jim and Sharon B.
Stayed Apr 2024
- 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