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Search results; Over 1,000 homes in Wailea, Wailea-Makena
Over 1,000 homes in Wailea, Wailea-Makena
Photo 1 of 29
Top guest favourite
Guest favourite
Apartment in Wailea
Ocean View! Pool! Ho'okipa @ Wailea Ekolu Village!
1 bedroom
,
·
1 bed
,
·
2 private bathrooms
25–30 Oct
25–30 Oct
£1,959 total
Show price breakdown
£1,959 total
,
·
5.0 out of 5 average rating, 75 reviews
5.0 (75)
Photo 1 of 29
Top guest favourite
Guest favourite
Villa in Kihei
Barefoot Luxury at it's Finest | 3bd Villa | E-201
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
3.5 bathrooms
3.5 bathrooms
2–7 Dec
2–7 Dec
£8,137 total
Show price breakdown
£8,137 total
Free cancellation
5.0 out of 5 average rating, 16 reviews
5.0 (16)
Photo 1 of 20
Top guest favourite
Guest favourite
Apartment in Wailea
Wailea Resort studio suite
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
4–9 Nov
4–9 Nov
£811 total
Show price breakdown
£811 total
Free cancellation
4.96 out of 5 average rating, 682 reviews
4.96 (682)
Photo 1 of 29
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
30 Sept – 5 Oct
30 Sept – 5 Oct
£1,799
£1,257 total
Show price breakdown
5.0 out of 5 average rating, 145 reviews
5.0 (145)
Photo 1 of 29
Top guest favourite
Guest favourite
Flat in Wailea
Great Location! Chic Wailea Getaway (1st floor)
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
19–24 Sept
19–24 Sept
£1,015 total
Show price breakdown
£1,015 total
4.98 out of 5 average rating, 60 reviews
4.98 (60)
Photo 1 of 29
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
12–17 Nov
12–17 Nov
£2,754 total
Show price breakdown
£2,754 total
4.94 out of 5 average rating, 335 reviews
4.94 (335)
Photo 1 of 29
Luxe
Luxe
Apartment in Wailea
Wailea Elua condo - Ocean Views | Gym | Pickleball
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
4–9 Oct
4–9 Oct
£4,676
£4,298 total
Show price breakdown
5.0 out of 5 average rating, 27 reviews
5.0 (27)
Photo 1 of 29
Top guest favourite
Guest favourite
Apartment in Wailea
A.R.A Retreats: Big Blue Pacific
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
11–16 Oct
11–16 Oct
£1,851
£1,661 total
Show price breakdown
4.96 out of 5 average rating, 185 reviews
4.96 (185)
Photo 1 of 29
Guest favourite
Guest favourite
Apartment in Wailea
Best Location, Panoramic Ocean View Remodel WE1508
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
11–16 Nov
11–16 Nov
£2,233 total
Show price breakdown
£2,233 total
Free cancellation
5.0 out of 5 average rating, 17 reviews
5.0 (17)
Photo 1 of 29
Top guest favourite
Guest favourite
Apartment in Wailea
Wailea Ekolu Village 2/2 with stunning ocean view!
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
10–15 Oct
10–15 Oct
£1,922
£1,628 total
Show price breakdown
4.94 out of 5 average rating, 199 reviews
4.94 (199)
Photo 1 of 29
Top guest favourite
Guest favourite
Apartment in Kihei
Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
24–29 Nov
24–29 Nov
£3,903
£3,516 total
Show price breakdown
Free cancellation
4.99 out of 5 average rating, 232 reviews
4.99 (232)
Photo 1 of 29
Guest favourite
Guest favourite
Flat in Wailea
Fabulous Ocean Views - Luxury 2br/2ba Penthouse
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
20–25 Sept
20–25 Sept
£6,978
£5,820 total
Show price breakdown
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Photo 1 of 29
Guest favourite
Guest favourite
Apartment in Wailea
Luxurious Tropical Retreat with Oceanview
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
17–22 Feb
17–22 Feb
£1,828 total
Show price breakdown
£1,828 total
4.92 out of 5 average rating, 48 reviews
4.92 (48)
Photo 1 of 29
Top guest favourite
Guest favourite
Apartment in Kihei
Mana Kai Palms Oceanfront Condo: Keawakapu Beach
2 bedrooms
2 bedrooms
,
·
2 king beds
2 king beds
,
·
2 bathrooms
2 bathrooms
19–24 Sept
19–24 Sept
£2,849
£2,504 total
Show price breakdown
4.97 out of 5 average rating, 106 reviews
4.97 (106)
Photo 1 of 29
Top guest favourite
Guest favourite
Apartment in Wailea
Palms 902 - Private Luxury Partial Ocean View
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
1–6 Oct
1–6 Oct
£1,448 total
Show price breakdown
£1,448 total
5.0 out of 5 average rating, 11 reviews
5.0 (11)
Photo 1 of 26
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
26 Sept – 1 Oct
26 Sept – 1 Oct
£1,146
£1,015 total
Show price breakdown
4.96 out of 5 average rating, 70 reviews
4.96 (70)
Photo 1 of 29
Top guest favourite
Guest favourite
Apartment in Kihei
Romantic, Luxury Retreat - Couples Only
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
2 bathrooms
2 bathrooms
27 Nov – 2 Dec
27 Nov – 2 Dec
£2,167
£1,949 total
Show price breakdown
Free cancellation
4.98 out of 5 average rating, 241 reviews
4.98 (241)
Photo 1 of 29
Top guest favourite
Guest favourite
Villa in Kihei
HO'OLEI DESIGNER VILLA24-4 AC WIFI BEACH POOL WALK
3 bedrooms
3 bedrooms
,
·
3 king beds
3 king beds
,
·
3.5 bathrooms
3.5 bathrooms
26 Sept – 1 Oct
26 Sept – 1 Oct
£6,580
£5,268 total
Show price breakdown
4.94 out of 5 average rating, 127 reviews
4.94 (127)
Photo 1 of 29
Top guest favourite
Guest favourite
Apartment in Kihei
Wailea Beachfront Direct Ocean Views 4 Bd/3 Ba
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
£8,172
£7,519 total
Show price breakdown
4.98 out of 5 average rating, 61 reviews
4.98 (61)
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