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

Guest favourite
Apartment in Wailea
Feel the Aloha at a Luxe Beach Chic Retreat
2 bedrooms, 3 beds, 2 private bathrooms
28 Aug – 2 Sept
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4.97 out of 5 average rating, 36 reviews
Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Molokini
2 bedrooms, 2 king beds, 2 bathrooms
6–11 Sept
4.94 out of 5 average rating, 332 reviews
Top guest favourite
Apartment in Wailea
Wailea Resort studio suite
1 bedroom, 1 bed, 1 bathroom
24–29 Aug
4.96 out of 5 average rating, 677 reviews
Guest favourite
Apartment in Wailea
A.R.A Retreats: The Townhouse
2 bedrooms, 4 beds, 2.5 bathrooms
19–24 Aug
4.9 out of 5 average rating, 357 reviews
Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Hideaway
2 bedrooms, 3 beds, 2 bathrooms
28 Aug – 2 Sept
4.97 out of 5 average rating, 154 reviews
Top guest favourite
Apartment in Wailea
Luxurious Tropical Retreat with Oceanview
1 bedroom, 2 beds, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Apartment in Wailea
Aloha Moon - The Honeymoon Hideaway
1 bedroom, 1 king bed, 1 bathroom
17–22 Aug
4.94 out of 5 average rating, 66 reviews
Luxe
Apartment in Wailea
Wailea Elua condo - Ocean Views | Gym | Pickleball
2 bedrooms, 4 beds, 2 bathrooms
25–30 Aug
5.0 out of 5 average rating, 25 reviews
Guest favourite
Apartment in Kihei
Beautifully Updated Oceanview Condo in Wailea
2 bedrooms, 4 beds, 2 bathrooms
25–30 Aug
5.0 out of 5 average rating, 5 reviews
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
Superhost
Apartment in Wailea
Polo Beach Club 409 | Ocean View, Pool + Hot Tub
2 bedrooms, 3 beds, 2 bathrooms
18–23 Aug
Superhost
Apartment in Kihei
3BR Luxury Villa w/ AC Superb Views - HLR 23-3
3 bedrooms, 3 king beds, 3.5 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 4 reviews
Apartment in Wailea
Beachfront 2BR condo w/ pool and ocean views
2 bedrooms, 2 bathrooms
27 Aug – 1 Sept
Guest favourite
Apartment in Wailea
Gaze out at Panoramic Ocean Views from an Airy Coastal Oasis
1 bedroom, 2 beds, 2 bathrooms
17–22 Aug
4.91 out of 5 average rating, 55 reviews
Top guest favourite
Apartment in Wailea
Wailea Surf Shack: Beaches, Shops & Golf!
1 bedroom, 2 beds, 2 bathrooms
25–30 Aug
5.0 out of 5 average rating, 141 reviews
Top guest favourite
Apartment in Wailea
Luxury Vacation at Special Summer 2026 Rates
1 bedroom, 2 beds, 2 bathrooms
17–22 Aug
4.96 out of 5 average rating, 70 reviews
Top guest favourite
Flat in Kihei
Wailea Ocean View Escape
1 bedroom, 2 beds, 2 bathrooms
25–30 Aug
4.98 out of 5 average rating, 61 reviews
Top guest favourite
Apartment in Kihei
Newly Renovated High-end 1 bed 2 bath Wailea Condo
1 bedroom, 2 beds, 2 bathrooms
17–22 Aug
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Apartment in Wailea
Maui Oasis Retreat At The Grand Champions #53
1 bedroom, 2 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 77 reviews