House vacation rentals in Wailea, Wailea-Makena

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Popular amenities for Wailea, Wailea-Makena house rentals

House rentals with a pool

Guest favorite

Home in Lahaina

4.91 out of 5 average rating, 127 reviews

Kaanapali Cottage ICC 29 Indoor/Outdoor Living

Sep 20 – 27

ﺩ.ﺇ1,489 per night
Guest favorite

Home in Kula

5.0 out of 5 average rating, 50 reviews

Hike on Scenic Trails at a Luxury Home on 7 Acres

Apr 21 – 28

ﺩ.ﺇ4,203 per night
Guest favorite

Home in Kihei

4.95 out of 5 average rating, 20 reviews

South Kihei Condo - steps to ocean and pool!

Jul 28 – Aug 4

ﺩ.ﺇ1,475 per night
Guest favorite

Home in Kihei

4.95 out of 5 average rating, 21 reviews

GORGEOUS PRIVATE HOME WITH POOL

Dec 4 – 11

ﺩ.ﺇ3,218 per night
Guest favorite

Home in Kihei

4.92 out of 5 average rating, 86 reviews

Maui Meadows Retreat B&B-3 BR-Ocean Views-AC-Pool

Aug 28 – Sep 4

ﺩ.ﺇ3,720 per night
Guest favorite

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

ﺩ.ﺇ995 per night
Guest favorite

Home in Kihei

5.0 out of 5 average rating, 18 reviews

Centrally located and steps to the beach!

Feb 17 – 24

ﺩ.ﺇ1,166 per night
Superhost

Home in Kihei

4.9 out of 5 average rating, 63 reviews

Maui Sunset Resort A102 - Aloha Mai, Remodel, Grou

Oct 25 – Nov 1

ﺩ.ﺇ1,101 per night

Weekly house rentals

Guest favorite

Home in Wailuku

4.92 out of 5 average rating, 134 reviews

Gratitude Bed and Breakfast BBWK2022/0001

Aug 9 – 16

ﺩ.ﺇ954 per night
Guest favorite

Home in Paia

4.89 out of 5 average rating, 158 reviews

Villa Parthenope in Paia bnb #3 *****

Feb 25 – Mar 4

ﺩ.ﺇ1,725 per night
Superhost

Home in Kihei

4.97 out of 5 average rating, 66 reviews

Exclusive Beachfront Cottage, Ocean Views, WiFi/AC

Jan 31 – Feb 7

ﺩ.ﺇ2,274 per night
Superhost

Home in Kihei

4.9 out of 5 average rating, 63 reviews

Whales and sunsets, front row seats every day!

Apr 1 – 8

ﺩ.ﺇ3,395 per night
Guest favorite

Home in Makawao

5.0 out of 5 average rating, 85 reviews

Private Luxurious Cottage

Mar 27 – Apr 3

ﺩ.ﺇ1,526 per night
Guest favorite

Home in Kihei

5.0 out of 5 average rating, 36 reviews

Cute Cottage-Large Outdoor Deck

Mar 20 – 27

ﺩ.ﺇ1,148 per night
Guest favorite

Home in Kihei

4.73 out of 5 average rating, 128 reviews

Kihei Bungalow w/tennis court steps from beach

Dec 9 – 16

ﺩ.ﺇ2,773 per night
Superhost

Home in Haiku-Pauwela

5.0 out of 5 average rating, 3 reviews

Romantic feel w/private bath & kitchen King bed

Apr 14 – 21

ﺩ.ﺇ625 per night

Private house rentals

Guest favorite

Home in Paia

4.95 out of 5 average rating, 62 reviews

Hale Ho'okipa Kai Cottage, County Licensed

Oct 15 – 22

ﺩ.ﺇ2,627 per night
Superhost

Home in Kihei

4.88 out of 5 average rating, 40 reviews

3 Bedroom Private House Kihei /Wailea Maui

Mar 2 – 9

ﺩ.ﺇ4,015 per night
Superhost

Home in Paia

4.93 out of 5 average rating, 30 reviews

Milo Surf Cottage

Oct 28 – Nov 4

ﺩ.ﺇ3,723 per night
Guest favorite

Home in Haiku-Pauwela

4.98 out of 5 average rating, 90 reviews

Pineapple Cottage Haiku Maui Lic#BBPH2015/0011

Nov 13 – 20

ﺩ.ﺇ1,478 per night
Superhost

Home in Kihei

4.64 out of 5 average rating, 11 reviews

Chic Beachfront Condo— Newly Remodeled — 2024

Mar 12 – 19

ﺩ.ﺇ2,122 per night
Guest favorite

Home in Haiku-Pauwela

5.0 out of 5 average rating, 61 reviews

Hookipa Farm: County Legal 3 Bedroom Home in Haiku

Dec 7 – 14

ﺩ.ﺇ2,653 per night
Superhost

Home in Paia

4.91 out of 5 average rating, 53 reviews

Paia Family Cottage

Jul 26 – Aug 2

ﺩ.ﺇ2,253 per night
Guest favorite

Home in Kihei

4.8 out of 5 average rating, 5 reviews

Luana Kai C209

Aug 30 – Sep 6

ﺩ.ﺇ981 per night

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

Destinations to explore

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  2. United States
  3. Hawaii
  4. Maui County
  5. Wailea-Makena
  6. Wailea
  7. House rentals