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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
A.R.A Retreats: Big Blue Pacific
2 bedrooms
,
·
3 beds
,
·
2 private bathrooms
11–16 Oct
11–16 Oct
£1,855
£1,664 total
Show price breakdown
,
·
4.96 out of 5 average rating, 185 reviews
4.96 (185)
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
£813 total
Show price breakdown
£813 total
Free cancellation
4.96 out of 5 average rating, 682 reviews
4.96 (682)
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
£8,182 total
Show price breakdown
£8,182 total
Free cancellation
5.0 out of 5 average rating, 16 reviews
5.0 (16)
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
£1,018 total
Show price breakdown
£1,018 total
4.98 out of 5 average rating, 60 reviews
4.98 (60)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Kihei
Private S. Maui home w/ocean views, pool, hot tub
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
17–22 Oct
17–22 Oct
£4,243 total
Show price breakdown
£4,243 total
4.93 out of 5 average rating, 104 reviews
4.93 (104)
Photo 1 of 29
Top guest favourite
Guest favourite
Apartment in Kihei
Luxe 2bed Wailea, 5-min walk to beach, ocean view,
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
28 Oct – 2 Nov
28 Oct – 2 Nov
£2,301 total
Show price breakdown
£2,301 total
Free cancellation
5.0 out of 5 average rating, 87 reviews
5.0 (87)
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
£3,897
£3,523 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
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
£2,238 total
Show price breakdown
£2,238 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
£1,926
£1,631 total
Show price breakdown
4.94 out of 5 average rating, 199 reviews
4.94 (199)
Photo 1 of 29
Superhost
Superhost
Flat in Wailea
* Wailea Elua 806 *
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
1–6 Oct
1–6 Oct
£4,116 total
Show price breakdown
£4,116 total
5.0 out of 5 average rating, 3 reviews
5.0 (3)
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
£4,685
£4,306 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 Kihei
Stunning Luxury Remodel I Wailea Beach Villas J206
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
17–22 Oct
17–22 Oct
£3,963 total
Show price breakdown
£3,963 total
4.98 out of 5 average rating, 144 reviews
4.98 (144)
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
£6,992
£5,831 total
Show price breakdown
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Photo 1 of 29
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
27 Oct – 1 Nov
27 Oct – 1 Nov
£1,407
£1,155 total
Show price breakdown
Free cancellation
4.98 out of 5 average rating, 209 reviews
4.98 (209)
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
£1,148
£1,017 total
Show price breakdown
4.96 out of 5 average rating, 70 reviews
4.96 (70)
Photo 1 of 23
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
2–7 Oct
2–7 Oct
£1,125
£945 total
Show price breakdown
4.97 out of 5 average rating, 316 reviews
4.97 (316)
Photo 1 of 29
Top guest favourite
Guest favourite
Flat in Wailea
A.R.A Retreats: Ocean Breeze
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
1–6 Oct
1–6 Oct
£1,816
£1,411 total
Show price breakdown
5.0 out of 5 average rating, 53 reviews
5.0 (53)
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
£1,425 total
Show price breakdown
£1,425 total
5.0 out of 5 average rating, 11 reviews
5.0 (11)
Photo 1 of 29
Guest favourite
Guest favourite
Apartment in Wailea
Wailea Gem-Remodeled Ocean View
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
8–13 Oct
8–13 Oct
£1,757
£1,390 total
Show price breakdown
4.96 out of 5 average rating, 202 reviews
4.96 (202)
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