Wailea holiday homes
We found 1,420 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:24 Oct - 31 Oct
Image gallery for Wailea Elua 702 - Beautifully Renovated, Stunning Ocean Views, Central AC, Wi-Fi

9.6 out of 10 rating
Exceptional
(13 reviews)
Wailea Elua 702 - Beautifully Renovated, Stunning Ocean Views, Central AC, Wi-Fi
Kihei, HI
7% off
Price is NZ$9,057
NZ$1,294 per night
includes taxes & fees
Image gallery for Ekahi 27A: Priceless Ocean View from a Private Lanai

9.8 out of 10 rating
Exceptional
(36 reviews)
Ekahi 27A: Priceless Ocean View from a Private Lanai
Kihei, HI
7% off
Price is NZ$7,068
NZ$1,010 per night
includes taxes & fees
Image gallery for 1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all!

10 out of 10 rating
Exceptional
(57 reviews)
1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all!
Kihei, HI
14% off
Price is NZ$7,946
NZ$1,135 per night
includes taxes & fees
Image gallery for Breath taking ocean and volcano views! Pool,Close to beaches and everything else

9.8 out of 10 rating
Exceptional
(152 reviews)
Breath taking ocean and volcano views! Pool,Close to beaches and everything else
Kihei, HI
7% off
Price is NZ$18,959
NZ$2,708 per night
includes taxes & fees
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Find the best place to stay - Wailea

Wailea Beach Villas
Sleeps 8 · 1 bathroom
9.8 out of 10
exceptional
(172 reviews)

Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
Sleeps 8 · 3 bedrooms · 3 bathrooms
10 out of 10
exceptional
(77 reviews)

Peaceful Island Escape Condo with four pools near all the best things in Maui!
Sleeps 4 · 1 bedroom · 1 bathroom
9.4 out of 10
exceptional
(113 reviews)

Direct Ocean Front Property Wailea Ekahi 42A Remodeled 2024 - 1 Bed 2 Full Bath
Sleeps 4 · 1 bedroom · 2 bathrooms
10 out of 10
exceptional
(22 reviews)
Top rated rentals - Wailea

to be done again
10 out of 10
exceptional
(92 reviews)
We recently had the pleasure of staying at a beautiful property in Wailea. The place was immaculately presented, boasting cleanliness and abundant sunshine. The views were simply breathtaking, and the amenities provided were top-notch.
The property’s location was incredibly convenient, being just a short stroll away from the beach, shops, and a variety of restaurants. Despite its central location, the place was peaceful and quiet, providing a serene retreat from the hustle and bustle.
One of the highlights of our stay was the stunning sunset views from our balcony. It was truly a sight to behold and made our evenings all the more special.
This place proved to be the perfect holiday spot for relaxation and quality time with friends and family. We couldn’t have asked for a better experience and highly recommend it to others looking for a memorable stay in Wailea.
Pablo G.
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