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

Top guest favourite
Apartment in Wailea
Stunning Wailea 2/2, AC, Upper Fl, walk to beach
2 bedrooms, 3 beds, 2 private bathrooms
2–7 Oct
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4.94 out of 5 average rating, 66 reviews
Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Curved Slab
2 bedrooms, 3 beds
25–30 Sept
4.95 out of 5 average rating, 363 reviews
Top guest favourite
Villa in Wailea
Luxury Oceanview Wailea Retreat with Sunset Views
3 bedrooms, 6 beds
8–13 Dec
4.98 out of 5 average rating, 50 reviews
Apartment in Wailea
Beachfront 2BR condo w/ pool and ocean views
2 bedrooms
28 Sept – 3 Oct
Top guest favourite
Apartment in Kihei
Peggy's Place - Best Beachfront Condo for Families
2 bedrooms, 3 beds
18–23 Sept
4.98 out of 5 average rating, 85 reviews
Top guest favourite
Apartment in Kihei
PURE ELEGANCE*OCEANVIEW Renovated Condo in WAILEA
2 bedrooms, 3 beds
26 Sept – 1 Oct
4.99 out of 5 average rating, 83 reviews
Top guest favourite
Apartment in Kihei
Groovy bright condo 2 bed / 2 bath South Kihei
2 bedrooms, 4 beds
21–26 Sept
4.93 out of 5 average rating, 205 reviews
Top guest favourite
Flat in Wailea
A.R.A Retreats: Ocean Breeze
2 bedrooms, 3 beds
1–6 Oct
5.0 out of 5 average rating, 52 reviews
Guest favourite
Apartment in Kihei
Wailea Elua 805 - 3 Bdrm Ocean View Luxury Condo
3 bedrooms, 5 beds
15–20 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Flat in Wailea
A.R.A Retreats: The Grand Pacific
2 bedrooms, 4 beds
19–24 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Apartment in Kihei
Wailea Beachfront Direct Ocean Views 4 Bd/3 Ba
4 bedrooms, 4 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 61 reviews
Top guest favourite
Apartment in Kihei
Mana Kai Palms Oceanfront Condo: Keawakapu Beach
2 bedrooms, 2 king beds
19–24 Sept
4.97 out of 5 average rating, 106 reviews
Luxe
Apartment in Wailea
Wailea Elua condo - Ocean Views | Gym | Pickleball
2 bedrooms, 4 beds
4–9 Oct
5.0 out of 5 average rating, 27 reviews
Guest favourite
Apartment in Wailea
Relaxing Wailea Condo Near Beaches
2 bedrooms, 4 beds
6–11 Oct
4.96 out of 5 average rating, 56 reviews
Top guest favourite
Guest suite in Kihei
Sweeping Panoramic Ocean Views - Private Ohana
2 bedrooms, 2 beds
9–14 Nov
4.99 out of 5 average rating, 143 reviews
Guest favourite
Flat in Wailea
Fabulous Ocean Views - Luxury 2br/2ba Penthouse
2 bedrooms, 3 beds
20–25 Sept
5.0 out of 5 average rating, 9 reviews
Luxe
Apartment in Wailea
*Fully Remodeled* Modern Island Style*
2 bedrooms, 3 beds
3–8 Nov
4.99 out of 5 average rating, 152 reviews
Guest favourite
Rooms in Kihei
Maui Hill 2BR Ocean View + Pool Near Wailea
2 bedrooms, 3 beds
24–29 Sept
4.85 out of 5 average rating, 13 reviews
Top guest favourite
Apartment in Kihei
Large 2 Bedroom 2 Bath Ground Unit Maui Parkshore
2 bedrooms, 4 beds
6–11 Oct
4.85 out of 5 average rating, 168 reviews