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

Top guest favourite
Flat in Kihei
Barefoot Luxury at it's Finest | 3bd Villa | E-201
3 bedrooms, 5 beds, 3.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Molokini
2 bedrooms, 2 king beds, 2 bathrooms
17–22 Jul
4.94 out of 5 average rating, 327 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
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
Top guest favourite
Apartment in Wailea
*Fully Remodeled* Modern Island Style*
2 bedrooms, 3 beds, 2 bathrooms
9–14 Jul
4.99 out of 5 average rating, 148 reviews
Guest favourite
Flat in Wailea
Wailea Ekahi 24C, Summer in Paradise in Style!
2 bedrooms, 6 beds, 2 bathrooms
2–7 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Curved Slab
2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
4.95 out of 5 average rating, 354 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
Flat in Wailea
Wailea Escape/Golf Views, Beaches & Family Comfort
2 bedrooms, 4 beds, 2 bathrooms
28 Jul – 2 Aug
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Apartment in Wailea
Grand Champions 169 Beautiful 3 BR on the Fairway!
3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
4.98 out of 5 average rating, 189 reviews
Flat in Wailea
* Wailea Elua 806 *
3 bedrooms, 3 beds, 2 bathrooms
6–11 Jul
Top guest favourite
Apartment in Kihei
Ekahi 22C Toes in the Sand in Under 2 Minutes
2 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
4.95 out of 5 average rating, 99 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
4.96 out of 5 average rating, 99 reviews
Superhost
Flat in Wailea
Ocean View w/AC - Wailea Elua 306
2 bedrooms, 2 beds, 2 bathrooms
6–11 Jul
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Wailea
Spacious 3BR/2BA Condo in Wailea
3 bedrooms, 3 beds, 2 bathrooms
3–8 Jul
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Apartment in Wailea
21A Grand Champions 1 Bed - Ulua & Mokapu beaches
1 bedroom, 2 beds, 1 bathroom
26–31 Jul
4.93 out of 5 average rating, 91 reviews
Guest favourite
Apartment in Kihei
Your Maui Luxury Escape - Wailea Beach Villas K107
2 bedrooms, 4 beds, 2 bathrooms
28 Aug – 3 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Room in Kihei
Garden Room, private bathroom, separate entrance
1 queen bed, 1 bathroom
25–30 Jul
4.95 out of 5 average rating, 456 reviews