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About South Maui/Southshore Vacation Rental Homes.
The second largest of Hawaii’s stunning eight islands, Maui is a mouth-watering, exotic resort with plenty to see and do throughout your stay. Similarly if a quiet, restful vacation rental is your preferred choice, then this too can be arranged.
The beautiful Southshore of Maui boasts two or three charming destinations. The town of Kihei is both well located and functional, one of the hottest places to stay in Maui as it avoids the breeze in comparison to other parts of the island and has a selection of holiday villas to choose from.
Sprawling coastline and dramatic scenery can be found south of Kihei in Wailea - a luxury resort with plenty of holiday villas and vacation rentals and trendy entertainment on offer. Take a stroll along the Wailea Beach Walk, with its stretching coastline providing the ideal viewing spot for whales.

Featured Vacation Rentals

South Maui/Southshore Vacation Rentals
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99 Rentals found
Beds: 2
Baths: 2
Sleeps: 4-5
Privacy in Paradise!
Surrounded by 3 fairways on "Old Blue Golf Course" with Golf, Ocean and Volcano Views.
$190
Day
Beds: 1
Baths: 1
Sleeps: 2-2
MAUI--Direct Oceanfront-- 1Bd/1Ba.Nice!.
DIRECT OCEANFRONT CONDO 1 Bdr/1 Bath.Upscale fully furnished, panoramic views.FREE HiSpeed Internet,Views!
$118
Day
Beds: 5
Baths: 2
Sleeps: 10-10
5 Bd Home Newly Remodeled Great Location
Maui Vacation Home, Great Location, Walk to beach, shops & restaurants. All the amenties of home provided.
$300
Day
Beds: 1
Baths: 1
Sleeps: 2-4
Luxury Ocean View - Remodeled, Updated
Wailea Ekahi, on Keawakapu Beach, surrounded by world class golf courses - close to fabulous dining & shopping
$195
Day
Beds: 2
Baths: 2
Sleeps: 4-4
Luxurious Oceanfront with private alev.
Impressive Oceanfront with private elevator 1,500sf with 300sf of covered lanai
$249
Day
Beds: 2
Baths: 2
Sleeps: 6-6
Condo Rental
Waiohului Beach Hale A101, Gorgeous 2 bedroom, 2 bath, Oceanview, Beach Front Condo.
$165
Day
Beds: 1
Baths: 1
Sleeps: 2-2
OCEANFRONT condo- Kihei Sands
Luxury oceanfront unit that is perfect for honeymooners or couples just wanting a romantic getaway.
$171
Day
Beds: 2
Baths: 2
Sleeps: 4-4
Ocean Views Every Room "Penthouse" A402
This is the top floor Penthouse in the front Ocean Facing building with.... 'Ocean Views from Every Room'
$135
Day
Beds: 4
Baths: 5
Sleeps: 6-8
Maui Meadows Guesthouse
Located in Wailea-Makena, Hawaii, USA
$599
Day
Beds: 1
Baths: 1
Sleeps: 2-4
BEACH FRONT BUILDING
ONE BEDROOM UNIT, IN A BEACH FRONT BUILDING,.AVAILABLE FOR SHORT & LONG TERM.
$75
Day
Beds: 1
Baths: 2
Sleeps: 2-4
Ekolu 107, Ekolu Village, Wailea
Amazing Oceanview Luxury Condo in Wailea's Ekolu Village, Air-Conditioned. NEW LOWER RATES!
$160
Day
Beds: 2
Baths: 2
Sleeps: 4-6
The Shores of Maui, Kihei
Oceanview 2/2 Top Floor, Pool, Spa, Tennis, Wifi, Walk to All!
$145
Day
Beds: 1
Baths: 1
Sleeps: 2-4
Oooh! Oooh! Pick Us!! Maui Vista
Renovated Ground Unit-Steps to the beach
$99
Day
Beds: 1
Baths: 2
Sleeps: 4-4
Kamaole Sands Inter Courtyard
Building 1. Close to the Beach and Pool
$115
Day
Beds: 2
Baths: 2
Sleeps: 4-4
Ocean Breeze Hideaway Bed & Breakfast
Oceanview bed & breakfast in sunny Kihei, Maui, up the hill overlooking Maalaea Bay, 10 minute walk to beach.
$560
Week
Beds: 3
Baths: 4
Sleeps: 8-10
Luxury Ocean View Villa at Wailea Beach
Ho'olei Luxury Villa - 3400 SQFT luxury Villa across from Grand Wailea Resort. Closest to Pool, Sleeps 10
$595
Day
Beds: 2
Baths: 2
Sleeps: 4-8
Affordable Luxury in Wailea
2 Bedroom Luxury condo in the best location on Maui.
$220
Day
Beds: 1
Baths: 1
Sleeps: 2-4
Oceanfront ...Awesome Penthouse View
Deluxe 1 Bedroom Top Floor Condo
$110
Day
Beds: 2
Baths: 2
Sleeps: 4-6
Spectacular Ocean Front Condo
60 feet off the ocean unobstructed view of Maalaea Bay and Haleakala Volcano.
$139
Day
Beds: 1
Baths: 1
Sleeps: 2-4
Kihei Akahi C-108
The resort of Kihei Akahi is located just across the street from Kamaole II beach in Kihei, Hawaii.
$630
Week
Beds: 1
Baths: 1
Sleeps: 2-4
Hono Kai Resort ,Maalaea Bay
Quiet, private ground level beachfront condo with fenced patio, steps from 5 mile long Sugar Beach
$145
Day
Beds: 2
Baths: 2
Sleeps: 4-6
Prime Beach front
Beautiful 2 bedroom beach front apartment
$295
Day
Beds: 2
Baths: 2
Sleeps: 4-4
Water and Pool Front Property
Delightful and relaxing condominium with marvelous view to whale watch.
$975
Week
Beds: 1
Baths: 2
Sleeps: 2-4
Ekahi Village, Wailea
Perfect Ekahi unit, quality renovation just completed! Air conditioning installed. Sleeps 4 with 2 full baths.
$275
Day
Beds: 1
Baths: 2
Sleeps: 2-4
Kamaole Sands resort, views, Inner Court
Our condo #1-204 at the Kamaole Sands resort is on the INNER COURTYARD with beautiful views; Bldg #1 unit #204
$125
Day


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