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Search results; Over 1,000 homes in Wailea-Makena
Over 1,000 homes in Wailea-Makena
Guest favourite
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
28 Aug – 2 Sept
$3,156 SGD
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for 5 nights
$3,156 SGD for 5 nights
,
·
4.97 out of 5 average rating, 36 reviews
4.97 (36)
Top guest favourite
Guest favourite
Apartment in Wailea
A.R.A Retreats: The Molokini
2 bedrooms
2 bedrooms
,
·
2 king beds
2 king beds
,
·
2 bathrooms
2 bathrooms
27 Aug – 1 Sept
27 Aug – 1 Sept
$3,868 SGD
$2,402 SGD
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for 5 nights
4.94 out of 5 average rating, 330 reviews
4.94 (330)
Top guest favourite
Guest favourite
Apartment in Wailea
Maui Oasis Retreat At The Grand Champions #53
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
8–13 Aug
8–13 Aug
$1,298 SGD
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for 5 nights
$1,298 SGD for 5 nights
5.0 out of 5 average rating, 77 reviews
5.0 (77)
Top guest favourite
Guest favourite
Apartment in Wailea
Ocean/Golf Course Views, Tropical Resort in Wailea
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
23–28 Aug
23–28 Aug
$2,175 SGD
$1,663 SGD
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for 5 nights
4.98 out of 5 average rating, 206 reviews
4.98 (206)
Top guest favourite
Guest favourite
Apartment in Wailea
Wailea Resort studio suite
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
10–15 Aug
10–15 Aug
$1,533 SGD
$1,405 SGD
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for 5 nights
4.96 out of 5 average rating, 676 reviews
4.96 (676)
Superhost
Superhost
Apartment in Wailea
Wailea Elua | Steps to Ulua Beach, Ocean Views
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
25–30 Aug
25–30 Aug
$5,441 SGD
$4,900 SGD
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for 5 nights
Top guest favourite
Guest favourite
Flat in Kihei
Maui Kamaole in Kihei | Ocean View, Pool, Hot Tub
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
18–23 Oct
18–23 Oct
$2,773 SGD
$2,538 SGD
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for 5 nights
Book early to save
Pay $0 today
Free cancellation
4.92 out of 5 average rating, 13 reviews
4.92 (13)
Superhost
Superhost
Apartment in Wailea
Polo Beach Club 409 | Ocean View, Pool + Hot Tub
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
15–20 Aug
15–20 Aug
$3,972 SGD
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for 5 nights
$3,972 SGD for 5 nights
Guest favourite
Guest favourite
Apartment in Wailea
A.R.A Retreats: The Townhouse
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
19–24 Aug
19–24 Aug
$3,945 SGD
$3,401 SGD
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for 5 nights
4.9 out of 5 average rating, 357 reviews
4.9 (357)
Top guest favourite
Guest favourite
Home in Kihei
South Maui Guesthouse
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
17–22 Aug
17–22 Aug
$1,702 SGD
$1,382 SGD
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for 5 nights
4.97 out of 5 average rating, 313 reviews
4.97 (313)
Top guest favourite
Guest favourite
Apartment in Wailea
Luxury Vacation at Special Summer 2026 Rates
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
7–12 Aug
7–12 Aug
$2,141 SGD
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for 5 nights
$2,141 SGD for 5 nights
4.96 out of 5 average rating, 69 reviews
4.96 (69)
Apartment in Wailea
Beachfront 2BR condo w/ pool and ocean views
2 bedrooms
2 bedrooms
,
·
2 bathrooms
2 bathrooms
8–13 Aug
8–13 Aug
$4,519 SGD
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for 5 nights
$4,519 SGD for 5 nights
Top guest favourite
Guest favourite
Guest suite in Kihei
Sweeping Panoramic Ocean Views - Private Ohana
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
3–8 Sept
3–8 Sept
$4,711 SGD
$4,122 SGD
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for 5 nights
4.99 out of 5 average rating, 142 reviews
4.99 (142)
Guest favourite
Guest favourite
Apartment in Wailea
Beach Front Wailea, Full Ocean View A/C, ELUA102
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
15–20 Aug
15–20 Aug
$4,777 SGD
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for 5 nights
$4,777 SGD for 5 nights
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Guest favourite
Guest favourite
Apartment in Kihei
Your Maui Luxury Escape - Wailea Beach Villas K107
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
28 Aug – 4 Sept
28 Aug – 4 Sept
$6,330 SGD
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for 7 nights
$6,330 SGD for 7 nights
5.0 out of 5 average rating, 11 reviews
5.0 (11)
Guest favourite
Guest favourite
Flat in Kihei
Chic Coastal Living in the Heart of Wailea
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
28 Sept – 3 Oct
28 Sept – 3 Oct
$3,286 SGD
$2,243 SGD
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for 5 nights
5.0 out of 5 average rating, 16 reviews
5.0 (16)
Superhost
Superhost
Apartment in Kihei
Whale Watch From Your Lanai
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
29 Aug – 3 Sept
29 Aug – 3 Sept
$4,772 SGD
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for 5 nights
$4,772 SGD for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Guest favourite
Guest favourite
Flat in Wailea
Wailea Oceanfront Luxury Front Row Escape
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
6–11 Aug
6–11 Aug
$9,285 SGD
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for 5 nights
$9,285 SGD for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Top guest favourite
Guest favourite
Apartment in Kihei
Spacious 3bd on Golf Course I Grand Champions 105
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
12–17 Aug
12–17 Aug
$2,261 SGD
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for 5 nights
$2,261 SGD for 5 nights
4.93 out of 5 average rating, 124 reviews
4.93 (124)
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