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Search results; Over 1,000 homes in Wailea-Makena

Top guest favourite
Apartment in Wailea
Ocean/Golf Course Views, Tropical Resort in Wailea
1 bedroom, 2 beds, 2 private bathrooms
1–6 Aug
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4.98 out of 5 average rating, 203 reviews
Guest favourite
Flat in Wailea
A.R.A Retreats: Birds Eye View
2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
4.97 out of 5 average rating, 101 reviews
Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Molokini
2 bedrooms, 2 king beds, 2 bathrooms
2–7 Aug
4.94 out of 5 average rating, 327 reviews
Top guest favourite
Apartment in Kihei
Luxe 2bed Wailea, 5-min walk to beach, ocean view,
2 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 81 reviews
Top guest favourite
Apartment in Wailea
Stunning Wailea 2/2, AC, Upper Fl, walk to beach
2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
4.94 out of 5 average rating, 62 reviews
Top guest favourite
Home in Kihei
Private S. Maui home w/ocean views, pool, hot tub
3 bedrooms, 4 beds, 3 bathrooms
8–13 Aug
4.93 out of 5 average rating, 100 reviews
Luxe
Apartment in Kihei
Wailea Ekolu – Oceanview in the Heart of Wailea
1 bedroom, 2 beds, 2 bathrooms
27 Jul – 1 Aug
4.98 out of 5 average rating, 60 reviews
Guest favourite
Flat in Wailea
Fabulous Ocean Views- Luxury 2 Bed 2 Bath
2 bedrooms, 3 beds, 2 bathrooms
10–15 Jul
5.0 out of 5 average rating, 7 reviews
Superhost
Apartment in Wailea
Wailea Elua 401 | Ocean Views | Pool | Hot Tub
2 bedrooms, 4 beds, 2 bathrooms
14–19 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Apartment in Kihei
Wailea Ekahi 12A | Ocean Views & Walk-Out Patio
1 bedroom, 2 beds, 1.5 bathrooms
22–27 Jul
5.0 out of 5 average rating, 5 reviews
Guest favourite
Flat in Kihei
Wailea Luxury Resort Vista
1 bedroom, 2 beds, 2 bathrooms
6–11 Aug
4.92 out of 5 average rating, 53 reviews
Top guest favourite
Flat in Wailea
Amazing location! Chic Maui Getaway (ground floor)
1 bedroom, 2 beds, 2 bathrooms
7–12 Jul
4.98 out of 5 average rating, 56 reviews
Top guest favourite
Apartment in Wailea
Boathouse Studio Condo in Wailea, Hawaii
1 bedroom, 1 queen bed, 1 bathroom
29 Jul – 3 Aug
4.98 out of 5 average rating, 476 reviews
Top guest favourite
Apartment in Wailea
*Fully Remodeled* Modern Island Style*
2 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
4.99 out of 5 average rating, 149 reviews
Guest favourite
Apartment in Wailea
Wailea Elua condo - Ocean Views | Gym | Pickleball
2 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 21 reviews
Home in Wailea
The Butterfly Home Maui
4 bedrooms, 5 beds, 3.5 bathrooms
26–31 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Apartment in Wailea
Luxurious Tropical Retreat with Oceanview
1 bedroom, 2 beds, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Villa in Wailea
Luxury Oceanview Wailea Retreat with Sunset Views
3 bedrooms, 6 beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 40 reviews
Top guest favourite
Apartment in Wailea
Modern Renovated Palms at Wailea Condo!
1 bedroom, 2 beds, 2 bathrooms
26–31 Jul
4.97 out of 5 average rating, 109 reviews