House vacation rentals in Wailea, Wailea-Makena
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Top-rated house rentals in Wailea, Wailea-Makena
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Wailea, Wailea-Makena house rentals
House rentals with a pool
Home in Lahaina
4.91 out of 5 average rating, 127 reviewsKaanapali Cottage ICC 29 Indoor/Outdoor Living
Sep 20 – 27
Home in Kula
5.0 out of 5 average rating, 50 reviewsHike on Scenic Trails at a Luxury Home on 7 Acres
Apr 21 – 28
Home in Kihei
4.95 out of 5 average rating, 20 reviewsSouth Kihei Condo - steps to ocean and pool!
Jul 28 – Aug 4
Home in Kihei
4.95 out of 5 average rating, 21 reviewsGORGEOUS PRIVATE HOME WITH POOL
Dec 4 – 11
Home in Kihei
4.92 out of 5 average rating, 86 reviewsMaui Meadows Retreat B&B-3 BR-Ocean Views-AC-Pool
Aug 28 – Sep 4
Home in Kihei
5.0 out of 5 average rating, 13 reviews*PANO EPIC OCEAN VIEW*RENOVATED*Dual AC*Owner MGMT
Aug 31 – Sep 7
Home in Kihei
5.0 out of 5 average rating, 18 reviewsCentrally located and steps to the beach!
Feb 17 – 24
Home in Kihei
4.9 out of 5 average rating, 63 reviewsMaui Sunset Resort A102 - Aloha Mai, Remodel, Grou
Oct 25 – Nov 1
Weekly house rentals
Home in Wailuku
4.92 out of 5 average rating, 134 reviewsGratitude Bed and Breakfast BBWK2022/0001
Aug 9 – 16
Home in Paia
4.89 out of 5 average rating, 158 reviewsVilla Parthenope in Paia bnb #3 *****
Feb 25 – Mar 4
Home in Kihei
4.97 out of 5 average rating, 66 reviewsExclusive Beachfront Cottage, Ocean Views, WiFi/AC
Jan 31 – Feb 7
Home in Kihei
4.9 out of 5 average rating, 63 reviewsWhales and sunsets, front row seats every day!
Apr 1 – 8
Home in Makawao
5.0 out of 5 average rating, 85 reviewsPrivate Luxurious Cottage
Mar 27 – Apr 3
Home in Kihei
5.0 out of 5 average rating, 36 reviewsCute Cottage-Large Outdoor Deck
Mar 20 – 27
Home in Kihei
4.73 out of 5 average rating, 128 reviewsKihei Bungalow w/tennis court steps from beach
Dec 9 – 16
Home in Haiku-Pauwela
5.0 out of 5 average rating, 3 reviewsRomantic feel w/private bath & kitchen King bed
Apr 14 – 21
Private house rentals
Home in Paia
4.95 out of 5 average rating, 62 reviewsHale Ho'okipa Kai Cottage, County Licensed
Oct 15 – 22
Home in Kihei
4.88 out of 5 average rating, 40 reviews3 Bedroom Private House Kihei /Wailea Maui
Mar 2 – 9
Home in Paia
4.93 out of 5 average rating, 30 reviewsMilo Surf Cottage
Oct 28 – Nov 4
Home in Haiku-Pauwela
4.98 out of 5 average rating, 90 reviewsPineapple Cottage Haiku Maui Lic#BBPH2015/0011
Nov 13 – 20
Home in Kihei
4.64 out of 5 average rating, 11 reviewsChic Beachfront Condo— Newly Remodeled — 2024
Mar 12 – 19
Home in Haiku-Pauwela
5.0 out of 5 average rating, 61 reviewsHookipa Farm: County Legal 3 Bedroom Home in Haiku
Dec 7 – 14
Home in Paia
4.91 out of 5 average rating, 53 reviewsPaia Family Cottage
Jul 26 – Aug 2
Home in Kihei
4.8 out of 5 average rating, 5 reviewsLuana Kai C209
Aug 30 – Sep 6
Quick stats about house rentals in Wailea, Wailea-Makena
Total rentals
50 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Rentals with a pool
30 properties have a pool
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
1.9K reviews
Nightly prices starting at
ﺩ.ﺇ257 before taxes and fees
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