filters

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

Photo 1 of 6
Guest favourite
Villa in Wailea
Luxury at it's Finest, Truly a Home away from Home
2 bedrooms, 4 beds, 2 private bathrooms
1–7 Sept
,
4.96 out of 5 average rating, 102 reviews
Photo 1 of 6
Top guest favourite
Flat in Wailea
A.R.A Retreats: Ocean Breeze
2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 50 reviews
Photo 1 of 6
Top guest favourite
Apartment in Wailea
A.R.A retreats: The OG
2 bedrooms, 3 beds, 2 bathrooms
4–9 Sept
4.91 out of 5 average rating, 354 reviews
Photo 1 of 6
Top guest favourite
Apartment in Wailea
*Fully Remodeled* Modern Island Style*
2 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
4.99 out of 5 average rating, 151 reviews
Photo 1 of 6
Top guest favourite
Guest suite in Kihei
Sweeping Panoramic Ocean Views - Private Ohana
2 bedrooms, 2 beds, 2 bathrooms
3–8 Sept
4.99 out of 5 average rating, 142 reviews
Photo 1 of 6
Top guest favourite
Apartment in Kihei
Groovy bright condo 2 bed / 2 bath South Kihei
2 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
4.93 out of 5 average rating, 204 reviews
Photo 1 of 6
Guest favourite
Apartment in Wailea
21B Grand Champions Studio -Ulua & Mokapu beaches
1 king bed, 1 bathroom
5–10 Sept
4.87 out of 5 average rating, 69 reviews
Photo 1 of 6
Top guest favourite
Villa in Wailea
Luxury Oceanview Wailea Retreat with Sunset Views
3 bedrooms, 6 beds, 2 bathrooms
24–29 Nov
5.0 out of 5 average rating, 48 reviews
Photo 1 of 6
Guest favourite
Flat in Wailea
Spacious 3BR/2BA Condo in Wailea
3 bedrooms, 3 beds, 2 bathrooms
19–24 Sept
4.92 out of 5 average rating, 13 reviews
Photo 1 of 6
Top guest favourite
Apartment in Kihei
Wailea Beachfront Direct Ocean Views 4 Bd/3 Ba
4 bedrooms, 4 beds, 3 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 61 reviews
Photo 1 of 6
Top guest favourite
Apartment in Kihei
Peggy's Place - Best Beachfront Condo for Families
2 bedrooms, 3 beds, 2 bathrooms
17–22 Sept
4.98 out of 5 average rating, 85 reviews
Photo 1 of 6
Apartment in Wailea
Beachfront 2BR condo w/ pool and ocean views
2 bedrooms, 2 bathrooms
9–14 Sept
Photo 1 of 6
Superhost
Flat in Wailea
* Wailea Elua 806 *
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 3 reviews
Photo 1 of 6
Guest favourite
Apartment in Kihei
Wailea Ekolu - Gorgeous Ocean View - AC, Smart TV!
2 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
4.89 out of 5 average rating, 131 reviews
Photo 1 of 6
Top guest favourite
Flat in Wailea
A.R.A Retreats: The Grand Pacific
2 bedrooms, 4 beds, 2.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 32 reviews
Photo 1 of 6
Top guest favourite
Apartment in Wailea
21A Grand Champions 1 Bed - Ulua & Mokapu beaches
1 bedroom, 2 beds, 1 bathroom
10–15 Oct
4.94 out of 5 average rating, 95 reviews
Photo 1 of 6
Luxe
Apartment in Wailea
Wailea Elua condo - Ocean Views | Gym | Pickleball
2 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 26 reviews
Photo 1 of 6
Guest favourite
Home in Kihei
Private S. Maui home w/ocean views, pool, hot tub
3 bedrooms, 4 beds, 3 bathrooms
12–17 Oct
4.93 out of 5 average rating, 102 reviews
Photo 1 of 6
Guest favourite
Flat in Kihei
Grand Champions - Ocean & Golf View, King Bed, A/C
2 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.92 out of 5 average rating, 132 reviews