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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
$3,152 SGD
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for 5 nights
$3,152 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
16–21 Aug
16–21 Aug
$3,863 SGD
$1,670 SGD
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for 5 nights
4.94 out of 5 average rating, 331 reviews
4.94 (331)
Top guest favourite
Guest favourite
Apartment in Wailea
A.R.A retreats: The OG
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
17–22 Aug
17–22 Aug
$2,527 SGD
$1,670 SGD
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for 5 nights
4.91 out of 5 average rating, 352 reviews
4.91 (352)
Top guest favourite
Guest favourite
Apartment in Wailea
Wailea Resort studio suite
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
24–29 Aug
24–29 Aug
$1,531 SGD
$1,403 SGD
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for 5 nights
4.96 out of 5 average rating, 677 reviews
4.96 (677)
Top guest favourite
Guest favourite
Apartment in Wailea
Luxurious Tropical Retreat with Oceanview
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
26–31 Oct
26–31 Oct
$2,605 SGD
$2,413 SGD
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for 5 nights
5.0 out of 5 average rating, 45 reviews
5.0 (45)
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
$3,857 SGD
$2,840 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
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
$4,501 SGD
$3,913 SGD
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for 5 nights
4.99 out of 5 average rating, 142 reviews
4.99 (142)
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
1–6 Sept
1–6 Sept
$1,943 SGD
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for 5 nights
$1,943 SGD for 5 nights
4.93 out of 5 average rating, 124 reviews
4.93 (124)
Luxe
Luxe
Apartment in Wailea
Wailea Elua condo - Ocean Views | Gym | Pickleball
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
25–30 Aug
25–30 Aug
$6,286 SGD
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for 5 nights
$6,286 SGD for 5 nights
5.0 out of 5 average rating, 25 reviews
5.0 (25)
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
17–22 Aug
17–22 Aug
$3,981 SGD
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for 5 nights
$3,981 SGD for 5 nights
Top guest favourite
Guest favourite
Apartment in Wailea
Aloha Moon - The Honeymoon Hideaway
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
21–26 Aug
21–26 Aug
$3,067 SGD
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for 5 nights
$3,067 SGD for 5 nights
4.94 out of 5 average rating, 66 reviews
4.94 (66)
Apartment in Wailea
Beachfront 2BR condo w/ pool and ocean views
2 bedrooms
2 bedrooms
,
·
2 bathrooms
2 bathrooms
27 Aug – 1 Sept
27 Aug – 1 Sept
$4,421 SGD
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for 5 nights
$4,421 SGD for 5 nights
Top guest favourite
Guest favourite
Apartment in Wailea
Wailea Surf Shack: Beaches, Shops & Golf!
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
25–30 Aug
25–30 Aug
$2,465 SGD
$2,241 SGD
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for 5 nights
5.0 out of 5 average rating, 141 reviews
5.0 (141)
Guest favourite
Guest favourite
Apartment in Kihei
Beautifully Updated Oceanview Condo in Wailea
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
25–30 Aug
25–30 Aug
$3,000 SGD
$2,451 SGD
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for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Superhost
Superhost
Apartment in Wailea
Wailea Elua 2401 | Wrap-Around Lanai & Ocean View
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
20–25 Aug
20–25 Aug
$4,098 SGD
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for 5 nights
$4,098 SGD for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Apartment in Kihei
Renovated Coastal Retreat- Steps from the Beach
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
3–8 Dec
3–8 Dec
$2,179 SGD
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for 5 nights
$2,179 SGD for 5 nights
New place to stay
New
Guest favourite
Guest favourite
Apartment in Wailea
Gaze out at Panoramic Ocean Views from an Airy Coastal Oasis
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
16–21 Aug
16–21 Aug
$2,093 SGD
$1,909 SGD
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for 5 nights
4.91 out of 5 average rating, 55 reviews
4.91 (55)
Superhost
Superhost
Apartment in Kihei
Beachfront Condo – Location, Location, Location
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
17–22 Aug
17–22 Aug
$4,715 SGD
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for 5 nights
$4,715 SGD for 5 nights
4.83 out of 5 average rating, 6 reviews
4.83 (6)
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
16–21 Aug
16–21 Aug
$2,138 SGD
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for 5 nights
$2,138 SGD for 5 nights
4.96 out of 5 average rating, 70 reviews
4.96 (70)
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