Wailea holiday homes
We found 1,422 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Wailea by choosing from 62 houses, 44 apartments and other holiday rentals. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll have the best amenities for spending time at your home away from home, which might include cable TV and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Wailea
Showing deals for:3 Oct - 10 Oct
Image gallery for Outstanding Location in Maui South Kihei & Wailea

9.8 out of 10 rating
Exceptional
(90 reviews)
Outstanding Location in Maui South Kihei & Wailea
Kihei, HI
7% off
Price is NZ$3,048
NZ$435 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Find properties near top attractions in Wailea
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Find the best place to stay - Wailea
Showing deals for: 2 Oct - 5 Oct
Wailea Beach Villas
Sleeps 8 · 1 bathroom
9.8 out of 10
exceptional
(172 reviews)
The current price is NZ$7,165
for 3 nights, 1 room
NZ$2,388 per night
includes taxes & fees
Top rated rentals - Wailea

Peaceful getaway
10 out of 10
exceptional
(22 reviews)
This unit is perfect for us as it’s so peaceful and the grounds are surrounded by gorgeous landscaping. We enjoyed the close vicinity to the pool. The furnishings of the condo inside and out are outstanding! Look forward to coming back again.
Anne Z.
Stayed Mar 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