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

Guest favourite
Apartment in Wailea
Wailea Gem-Remodeled Ocean View
1 bedroom, 2 beds, 2 private bathrooms
8–13 Oct
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4.96 out of 5 average rating, 202 reviews
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, 33 reviews
Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Curved Slab
2 bedrooms, 3 beds, 2 bathrooms
19–24 Sept
4.95 out of 5 average rating, 362 reviews
Top guest favourite
Apartment in Kihei
Groovy bright condo 2 bed / 2 bath South Kihei
2 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.93 out of 5 average rating, 205 reviews
Top guest favourite
Flat in Kihei
Sea Suite: Ocean View · Walk to Beach & Food · AC
2 bedrooms, 2 king beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 6 reviews
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
Guest favourite
Home in Kihei
Private S. Maui home w/ocean views, pool, hot tub
3 bedrooms, 4 beds, 3 bathrooms
17–22 Oct
4.93 out of 5 average rating, 104 reviews
Top guest favourite
Flat in Wailea
Great Location! Chic Wailea Getaway (1st floor)
1 bedroom, 2 beds, 2 bathrooms
19–24 Sept
4.98 out of 5 average rating, 60 reviews
Top guest favourite
Apartment in Kihei
Very Comfortable Kamaole Sands Condo Sleeps 4
1 bedroom, 2 beds, 2 bathrooms
17–22 Sept
4.99 out of 5 average rating, 150 reviews
Top guest favourite
Apartment in Kihei
Luxury Vacationing Modern Condo Sept Specials
2 bedrooms, 2 king beds, 2 bathrooms
15–20 Oct
4.96 out of 5 average rating, 182 reviews
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, 97 reviews
Top guest favourite
Apartment in Kihei
Spacious 3bd on Golf Course I Grand Champions 105
3 bedrooms, 4 beds, 2 bathrooms
14–19 Nov
4.93 out of 5 average rating, 127 reviews
Top guest favourite
Flat in Wailea
Wailea Escape/Golf Views, Beaches & Family Comfort
2 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 27 reviews
Luxe
Apartment in Wailea
Wailea Elua condo - Ocean Views | Gym | Pickleball
2 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 27 reviews
Guest favourite
Flat in Wailea
Spacious 3BR/2BA Condo in Wailea
3 bedrooms, 3 beds, 2 bathrooms
22–27 Sept
4.92 out of 5 average rating, 13 reviews
Guest favourite
Flat in Kihei
Wailea Beachfront Escape — A One-of-a-Kind Retreat
1 bedroom, 1 king bed, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 8 reviews
Superhost
Flat in Wailea
* Wailea Elua 806 *
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 3 reviews
Guest favourite
Apartment in Kihei
Wailea Blue Golf Course Condo-Walk to Shops, Beach
2 bedrooms, 3 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 5 reviews
Guest favourite
Flat in Wailea
Fabulous Ocean Views - Luxury 2br/2ba Penthouse
2 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 9 reviews