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

Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Molokini
2 bedrooms, 3 beds, 2 private bathrooms
2–7 Aug
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4.94 out of 5 average rating, 329 reviews
Top guest favourite
Apartment in Kihei
Luxe 2bed Wailea, 5-min walk to beach, ocean view,
2 bedrooms, 3 beds
19–24 Sept
5.0 out of 5 average rating, 82 reviews
Top guest favourite
Villa in Wailea
Luxury Oceanview Wailea Retreat with Sunset Views
3 bedrooms, 6 beds
25–30 Oct
5.0 out of 5 average rating, 41 reviews
Top guest favourite
Flat in Kihei
Barefoot Luxury at it's Finest | 3bd Villa | E-201
3 bedrooms, 5 beds
7–12 Nov
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Apartment in Wailea
Grand Champions 169 Beautiful 3 BR on the Fairway!
3 bedrooms, 4 beds
22–27 Aug
4.98 out of 5 average rating, 191 reviews
Top guest favourite
Apartment in Kihei
Stunning Luxury Remodel I Wailea Beach Villas J206
2 bedrooms, 3 beds
7–12 Aug
4.98 out of 5 average rating, 139 reviews
Guest favourite
Home in Kihei
Private S. Maui home w/ocean views, pool, hot tub
3 bedrooms, 4 beds
8–13 Aug
4.93 out of 5 average rating, 100 reviews
Top guest favourite
Apartment in Kihei
Wailea Beachfront Direct Ocean Views 4 Bd/3 Ba
4 bedrooms, 4 beds
28 Jul – 2 Aug
4.98 out of 5 average rating, 60 reviews
Luxe
Apartment in Wailea
Wailea Elua condo - Ocean Views | Gym | Pickleball
2 bedrooms, 4 beds
12–17 Aug
5.0 out of 5 average rating, 22 reviews
Guest favourite
Apartment in Wailea
A.R.A Retreats: The Townhouse
2 bedrooms, 4 beds
2–7 Aug
4.9 out of 5 average rating, 356 reviews
Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Waterfall
2 bedrooms, 3 beds
6–11 Aug
4.94 out of 5 average rating, 262 reviews
Top guest favourite
Apartment in Wailea
*Fully Remodeled* Modern Island Style*
2 bedrooms, 3 beds
5–10 Oct
4.99 out of 5 average rating, 149 reviews
Top guest favourite
Apartment in Kihei
Refined Resort Wailea Oceanview Vistas
2 bedrooms, 3 beds
14–19 Jul
5.0 out of 5 average rating, 30 reviews
Guest favourite
Apartment in Wailea
The BEST Condo in Wailea: Elua Resort 1002
2 bedrooms, 2 king beds
21–26 Jul
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Apartment in Wailea
Stunning Wailea 2/2, AC, Upper Fl, walk to beach
2 bedrooms, 3 beds
29 Aug – 3 Sept
4.94 out of 5 average rating, 63 reviews
Guest favourite
Flat in Wailea
Wailea Ekahi 24C, Summer in Paradise in Style!
2 bedrooms, 6 beds
5–10 Aug
5.0 out of 5 average rating, 8 reviews
Superhost
Flat in Wailea
Wailea Oceanfront Luxury Front Row Escape
2 bedrooms, 3 beds
19–24 Jul
5.0 out of 5 average rating, 4 reviews
Flat in Kihei
Wailea Beachfront Escape — A One-of-a-Kind Retreat
1 bedroom, 1 bed
16–21 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Apartment in Wailea
21A Grand Champions 1 Bed - Ulua & Mokapu beaches
1 bedroom, 2 beds
26–31 Jul
4.93 out of 5 average rating, 92 reviews