South Kihei vacation rentals

We found 2,586 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

Indoor Dining Area
Living Room Area
Private Wailea/Kihei retreat just minutes from Maui’s most beautiful beaches
Unwind after beach days with peaceful outdoor living and island breezes
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 Grounds are well maintained and tropical
Golfing in Paradise
Ocean view from the lanai, kitchen and living area
Kihei Akahi is a beautiful complex and is in the middle of South Kihei.
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!!
Terrific Maui Vista!!
BBQ areas at the Maui Vista
Wailea Golf Course, get your game on!
Sparkling Pool Area
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
Living Room
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.
Sectional sofa can turn into extra queen bed
View from lanai before sunrise coming up over Haleakala
View from lanai towards ocean
Pool area looking 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
Living area
Great bedroom with king bed
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
Exterior
Terrace/patio
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
Community swimming pool on property
Granite countertop, living area
Living area, dining, and kitchen
Living area looks out to lanai and lush landscaping
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.
Bring your rackets!
You'll  love the lanai which is right near the sunken pool area, creating quiet
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
Beautiful view to the pool
Maui Tropical Plantation.
Parking at the Maui Banyan is convenient and covered
Freds Mexican Cafe & Moose's is located just across the street from Kamaole II.
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
View of the living area from the kitchen.
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
View from our Lanai.
Circular stairs leads up to Master bedroom
Living Room looking out to lanai
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!
Room
Room
Pool
Interior
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
Lower Swimming Pool
View from Lanai
Grounds outside our Lanai
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
Wonderful BBQ areas at the complex
Many golf courses on Island! Get your game on
Living area with queen sofa sleeper
Maui Vista grounds are surrounded by tropical beauty,
Excellent
(63 reviews)

BEST RATES in Low Season!~Never a better time to make a trip to Paradise!!

Kihei

8% off
$187
$1,311 for 7 nights
All fees included
BEST RATES in Low Season!~Never a better time to make a trip to Paradise!!
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 !!
Dining
Property grounds
Living area
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!
Resort grounds
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
Dining
Outdoor dining
Living area
Interior
Exceptional
(31 reviews)

Kihei Getaway in Paradise

Kihei

8% off
$389
$2,724 for 7 nights
All fees included
Kihei Getaway in Paradise
Pool
Property grounds
Dining
Private kitchen
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
Outdoor dining
Exterior detail
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.