South Kihei vacation rentals

We found 2,587 vacation rentals — enter your dates for availability
Select from 37 houses, 1829 condos, and other vacation rentals to find the perfect place for your stay in South Kihei. Vacation rentals offer the amenities you expect for your family, friends, or furry companion, such as a garden and pool. You'll be sure to find a rental that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - South Kihei

Showing deals for:Nov 20 - Nov 27

Kitchen Area - Island Bar
Living Room Area
Unwind after beach days with peaceful outdoor living and island breezes
Private Wailea/Kihei retreat just minutes from Maui’s most beautiful beaches
Exceptional
(103 reviews)

Luxury 3BR Wailea Kihei Retreat. Walk to Beaches, Private Lanai, Newly Remodeled

Kihei

8% off
$707
$4,946 for 7 nights
All fees included
Luxury 3BR Wailea Kihei Retreat. Walk to Beaches, Private Lanai, Newly Remodeled
Kihei Akahi is a beautiful complex and is in the middle of South Kihei.
Golfing in Paradise
Kihei Akahi Grounds are well maintained and tropical
Private bedroom with queen bed and closet space for your clothing
Excellent
(42 reviews)

~Amazing Ocean View on 3rd flr~ MAUI AWAITS YOU!!

Kihei

9% off
$199
$1,395 for 7 nights
All fees included
~Amazing Ocean View on 3rd flr~ MAUI AWAITS YOU!!
Sparkling Pool Area
BBQ areas at the Maui Vista
Wailea Golf Course, get your game on!
Maui Vista is popular in affordability and comfort comfortable
Wonderful
(51 reviews)

Escape to Paradise at the Maui Vista "3rd Bld 1b/1b"

Kihei

9% off
$178
$1,245 for 7 nights
All fees included
Escape to Paradise at the Maui Vista "3rd Bld 1b/1b"
Living Room Sofa/bed
Lower Swimming Pool
Entry Sign by Kihei Rd
Living Room from Master Bedroom Railing
Exceptional
(95 reviews)

D211 Quiet & Private 2br2ba near Wailea 2026 Discount 10% 7 nts or more.

Kihei

6% off
$444
$3,106 for 7 nights
All fees included
D211 Quiet & Private 2br2ba near Wailea 2026 Discount 10% 7 nts or more.
Pool area looking towards ocean
View from lanai before sunrise coming up over Haleakala
Sectional sofa can turn into extra queen bed
View from lanai towards ocean
Exceptional
(92 reviews)

Unbeatable Location at Kamaole III Beach - Kam Sands Bldg. 1

Kihei

8% off
$578
$4,049 for 7 nights
All fees included
Unbeatable Location at Kamaole III Beach - Kam Sands Bldg. 1
Living area
Exterior
Lanai view
Living area
Exceptional
(110 reviews)

Oceanview Top Floor Condo, with Internet Access.

Kihei

8% off
$213
$1,492 for 7 nights
All fees included
Oceanview Top Floor Condo, with Internet Access.
Private kitchen
Beach
Terrace/patio
Property grounds
Exceptional
(65 reviews)

Hotel Zoned! Steps to the Beach, Dining and Shopping! Summer Specials! Inquire

Kihei

8% off
$222
$1,554 for 7 nights
All fees included
Hotel Zoned! Steps to the Beach, Dining and Shopping! Summer Specials! Inquire
Dining area, kitchen
Granite countertop, living area
Living area, dining, and kitchen
Community swimming pool on property
Exceptional
(140 reviews)

Kihei, Maui Ground Floor Tropical Getaway - Across street from beach

Kihei

8% off
$219
$1,532 for 7 nights
All fees included
Kihei, Maui Ground Floor Tropical Getaway - Across street from beach
Enjoy 2 couches and two chairs, one a recliner
Lush landscaping provides shade or sun and a waterfall.
You'll  love the lanai which is right near the sunken pool area, creating quiet
Bring your rackets!
Exceptional
(49 reviews)

S. Kihei spacious garden condo, 2 lanais

Kihei

8% off
$291
$2,038 for 7 nights
All fees included
S. Kihei spacious garden condo, 2 lanais
Parking at the Maui Banyan is convenient and covered
Maui Tropical Plantation.
Beautiful view to the pool
Just one of Maui's great golf courses to test you skills.
Exceptional
(29 reviews)

TROPICAL MAUI!!! Visit and stay in Comfort and Style...1b/2b

Kihei

9% off
$213
$1,489 for 7 nights
All fees included
TROPICAL MAUI!!! Visit and stay in Comfort and Style...1b/2b
Pool
Relax in your private lanai and enjoy the ocean view. This is paradise!
Feel right at home in this fully-equipped kitchen with granite countertops.
Kamaole Sands resort amenities include pools, hot tubs, gym and tennis.
Exceptional
(89 reviews)

Maui Escape - Oceanview 70 Yds to Beach, GND Flr, Bldg10 - Everything You Need!

Kihei

8% off
$312
$2,185 for 7 nights
All fees included
Maui Escape - Oceanview 70 Yds to Beach, GND Flr, Bldg10 - Everything You Need!
Living Room looking out to lanai
View from our Lanai.
Living Room
Water fountain greets you when you first arrive
Exceptional
(73 reviews)

Highly desirable top floor unit with garden and ocean view has hot summer deals!

Kihei

8% off
$432
$3,025 for 7 nights
All fees included
Highly desirable top floor unit with garden and ocean view has hot summer deals!
Exterior
Room
Interior
Pool
Exceptional
(51 reviews)

Blue Sky Escapes One bedroom Beach Steps Away! Pool Hot tub

Kihei

8% off
$294
$2,061 for 7 nights
All fees included
Blue Sky Escapes One bedroom Beach Steps Away! Pool Hot tub
Grounds outside our Lanai
View from Lanai
New Kitchen
Lower Swimming {Pool from our Lanai
Exceptional
(59 reviews)

# 107 Lovely Grnd Flr King bed Unit, accross the street is a white sand beach

Kihei

7% off
$251
$1,759 for 7 nights
All fees included
# 107 Lovely Grnd Flr King bed Unit, accross the street is a white sand beach
Living Room with Circular Staircase
Sunset from lanai
Downstairs bedroom with king bed
Pool from lanai
Exceptional
(20 reviews)

Beautiful Kamaole Sands Oceanview Condominium !!

Kihei

9% off
$318
$2,223 for 7 nights
All fees included
Beautiful Kamaole Sands Oceanview Condominium !!
Private kitchen
Property grounds
Dining
view from lanai over the complex grounds
Exceptional
(165 reviews)

Kamaole Sands Remodeled 1 Bed 2 bathroom, Split AC, king bed

Kihei

8% off
$394
$2,760 for 7 nights
All fees included
Kamaole Sands Remodeled 1 Bed 2 bathroom, Split AC, king bed
Spectacular ocean view from this beautiful condo lanai
Maui Tropical Plantation
Shores of Maui Resort
Golfing on Maui is one of the best
Exceptional
(33 reviews)

Shores of Maui, sensational ocean view in Paradise!

Kihei

8% off
$233
$1,632 for 7 nights
All fees included
Shores of Maui, sensational ocean view in Paradise!
Pool 1
Ocean view from living room
Living room, kitchen
Building 3 grounds
Exceptional
(7 reviews)

Top Floor Maui Vista with Ocean View, AC, 5min Walk to Beach

Kihei

8% off
$562
$3,934 for 7 nights
All fees included
Top Floor Maui Vista with Ocean View, AC, 5min Walk to Beach
Living area
Outdoor dining
Dining
Pool
Exceptional
(31 reviews)

Kihei Getaway in Paradise

Kihei

8% off
$389
$2,724 for 7 nights
All fees included
Kihei Getaway in Paradise
Dining
Property grounds
Private kitchen
Interior
Very Good
(19 reviews)

Ocean View Condo Across from Best Beach in Maui (Kamaole Beach Royale 202)

Kihei

8% off
$306
$2,142 for 7 nights
All fees included
Ocean View Condo Across from Best Beach in Maui (Kamaole Beach Royale 202)
Private kitchen
Living area
Exterior detail
Outdoor dining
Exceptional
(126 reviews)

Artistic Top-Floor Tropical Penthouse – Steps to Maui’s Best Beach

Kihei

16% off
$295
$2,063 for 7 nights
All fees included
Artistic Top-Floor Tropical Penthouse – Steps to Maui’s Best Beach
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more
  • More for less

    More space, more privacy, more amenities — more value
  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Frequently asked questions

Can I find vacation rentals in South Kihei?
Yes, you can find vacation rentals close to popular points of interest in South Kihei, or you can choose a secluded option if you're looking for relaxation.
How many vacation rentals will I find in South Kihei?
Expedia has 37 vacation rentals for your stay in South Kihei.
What can I see and do in South Kihei?
Kamaole Beach Park 2 and Kamaole Beach Park 3 are a couple of lovely local spots to get outside and enjoy nature. You'll find favorite places to visit like Wailea Beach and Haleakala National Park in the larger area.
What are vacation rentals like in South Kihei?
Vacation rentals are privately owned properties you can book for a couple days or more in South Kihei. Vacation rentals feature amenities like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from shared hotel elevators and bustling concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for small groups.