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

Top guest favourite
Apartment in Wailea
Aloha Moon - The Honeymoon Hideaway
1 bedroom, 1 bed, 1 private bathroom
9–14 Sept
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4.94 out of 5 average rating, 66 reviews
Top guest favourite
Apartment in Wailea
A.R.A retreats: The OG
2 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
4.91 out of 5 average rating, 355 reviews
Luxe
Apartment in Wailea
*Fully Remodeled* Modern Island Style*
2 bedrooms, 3 beds, 2 bathrooms
12–17 Oct
4.99 out of 5 average rating, 152 reviews
Top guest favourite
Flat in Wailea
A.R.A Retreats: Ocean Breeze
2 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 51 reviews
Top guest favourite
Guest suite in Kihei
Sweeping Panoramic Ocean Views - Private Ohana
2 bedrooms, 2 beds, 2 bathrooms
4–9 Oct
4.99 out of 5 average rating, 143 reviews
Top guest favourite
Apartment in Wailea
Grand Champions Villas in Wailea, Maui
2 bedrooms, 3 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Villa in Wailea
Luxury Oceanview Wailea Retreat with Sunset Views
3 bedrooms, 6 beds, 2 bathrooms
8–13 Dec
4.98 out of 5 average rating, 49 reviews
Top guest favourite
Flat in Kihei
Wailea Ocean View Escape
1 bedroom, 2 beds, 2 bathrooms
20–25 Sept
4.98 out of 5 average rating, 63 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
Apartment in Wailea
A.R.A Retreats: The Townhouse
2 bedrooms, 4 beds, 2.5 bathrooms
6–11 Sept
4.9 out of 5 average rating, 358 reviews
Top guest favourite
Apartment in Kihei
Stunning Luxury Remodel I Wailea Beach Villas J206
2 bedrooms, 4 beds, 2 bathrooms
17–22 Oct
4.98 out of 5 average rating, 142 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
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, 126 reviews
Top guest favourite
Apartment in Kihei
Romantic, Luxury Retreat w/Ocean View-Couples Only
1 bedroom, 1 king bed, 2 bathrooms
25–30 Apr
4.99 out of 5 average rating, 197 reviews
Flat in Kihei
The Best Condo in Wailea Ekahi Village!
2 bedrooms, 3 beds, 2 bathrooms
5–10 Sept
New place to stay
Guest favourite
Flat in Wailea
Spacious 3BR/2BA Condo in Wailea
3 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
4.92 out of 5 average rating, 13 reviews
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, 103 reviews
Top guest favourite
Apartment in Kihei
Luxury condo w/THE BEST view & location on Maui!
2 bedrooms, 3 beds, 2 bathrooms
5–10 Sept
5.0 out of 5 average rating, 56 reviews
Top guest favourite
Apartment in Wailea
Fairway-front 2BR, pool, walk to Wailea Beach
2 bedrooms, 3 beds, 2 bathrooms
5–10 Sept
4.95 out of 5 average rating, 168 reviews