Wailea family rentals
We found 1,434 family rentals — enter your dates for availability
Find the best place to stay - Wailea

Breathtaking Ocean Views! Beach Front Luxury Penthouse, Polo Beach 2 Bed/2 Bath
Sleeps 5 · 2 bedrooms · 2 bathrooms
10 out of 10
exceptional
(15 reviews)
Top rated rentals - Wailea

Incredible Stay
10 out of 10
exceptional
(83 reviews)
The host was wonderful, the place was clean - full of amenities (so cool to have beach chairs, snorkels, and umbrellas) - and very family friendly. I really enjoyed BBQ'ing on the lanai, what an amazing view from there - the pictures do not do it justice!
We couldn't fault the place at all - a lovely place to stay for our 10 year wedding anniversary (with 2 kids in tow!)
Kevin A.
Stayed Apr 2023
Find spaces that suit your style
House
Condo/Apartment
- 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






