Kailua guest houses

We found 13 guest houses — enter your dates for availability
Select from 139 houses, 34 apartments and other holiday rentals to find the perfect place for your stay in Kailua. Holiday rentals provide the best amenities for your family, friends or furry companion, such as air conditioning and Wi-Fi. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Find spaces that suit your style

Explore Kailua guest house rentals

Image of Kaneohe Bay B&B Waterfront & mountain views galore~saltwater pool

Kaneohe Bay B&B Waterfront & mountain views galore~saltwater pool

Sleeps 4 · 2 bedrooms · 2+ bathrooms
9.8 out of 10
exceptional
(148 reviews)
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Top rated guest house rentals - Kailua

Bar (on property)
Great spot in Waikiki
9.6 out of 10, Exceptional, 197 reviews
"Great new hotel... not too pushy with the time share offer, which was a welcome relief, very helpful and attentive staff, and best feature of all was the toilets (youll see what I mean if you stay here!). Fantastic pool and facilities on the 8th floor, and a perfect place to watch the Friday fireworks. Great central location, close to shop and restaurants. Highly recommend this place!"
Joshua
Joshua
Stayed Jan 2025
Marriott Vacation Club, Waikiki

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    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