South Kihei vacation rentals

We found 2,580 vacation rentals — enter your dates for availability
Select from 37 houses, 1836 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 27 - Dec 4

Indoor Dining Area
Living Room Area
Kitchen Area - Island Bar
Unwind after beach days with peaceful outdoor living and island breezes
Exceptional
(104 reviews)

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

Kihei

8% off
$664
$4,647 for 7 nights
All fees included
Luxury 3BR Wailea Kihei Retreat. Walk to Beaches, Private Lanai, Newly Remodeled
Lanai for outdoor dining and with perfect view for turtle or whale watching.
Pool and ocean view from the remodeled rooftop.
Main bedroom with comfortable King bed and ocean view.
Drone shot of the Royal Mauian nestled between Kam 1 and Kam 2 beaches.
Exceptional
(49 reviews)

Breathtaking Ocean Front Views. Incredible Reviews.

Kihei

6% off
$902
$6,314 for 7 nights
All fees included
Breathtaking Ocean Front Views. Incredible Reviews.
Ocean view from the lanai, kitchen and living area
Golfing in Paradise
Kihei Akahi is a beautiful complex and is in the middle of South Kihei.
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!!
Room
Beachfront property
Exterior
Living area
Exceptional
(46 reviews)

Classic Beachfront Studio Apartment Right On Charley Young Beach

Kihei

8% off
$211
$1,475 for 7 nights
All fees included
Classic Beachfront Studio Apartment Right On Charley Young Beach
You'll  love the lanai which is right near the sunken pool area, creating quiet
Lush landscaping provides shade or sun and a waterfall.
Enjoy 2 couches and two chairs, one a recliner
Bring your rackets!
Exceptional
(49 reviews)

S. Kihei spacious garden condo, 2 lanais

Kihei

8% off
$298
$2,085 for 7 nights
All fees included
S. Kihei spacious garden condo, 2 lanais
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

7% off
$544
$3,806 for 7 nights
All fees included
Top Floor Maui Vista with Ocean View, AC, 5min Walk to Beach
Kitchen with deep SIL Granite sink.  Updated pic January 2023
Ocean for days!
Pool view from the roof
Exterior
Exceptional
(197 reviews)

Ocean Front Renovated 2 BR/BA Luxury Condo w/ A/C . 2nd Floor Unobstructed View

Kihei

8% off
$500
$3,500 for 7 nights
All fees included
Ocean Front Renovated 2 BR/BA Luxury Condo w/ A/C . 2nd Floor Unobstructed View
Dining area, kitchen
Granite countertop, living area
Living area looks out to lanai and lush landscaping
Community swimming pool on property
Exceptional
(140 reviews)

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

Kihei

8% off
$204
$1,429 for 7 nights
All fees included
Kihei, Maui Ground Floor Tropical Getaway - Across street from beach
Room
private pool
Beautiful views from rooftop terrace
ocean and west Maui mountain views from Lanai
Wonderful
(130 reviews)

Top Floor Unit ~ Endless Ocean Views

Kihei

6% off
$413
$2,890 for 7 nights
All fees included
Top Floor Unit ~ Endless Ocean Views
Exterior
Pool
Living area
Living area
Exceptional
(181 reviews)

Read our Reviews! Newly Updated Condo! Perfect Getaway Steps to Beach & Dining!

Kihei

8% off
$263
$1,838 for 7 nights
All fees included
Read our Reviews! Newly Updated Condo! Perfect Getaway Steps to Beach & Dining!
Kamaole Sands fountain
Kamaole Sands refreshing swimming pool
Living area
Kamaole Sands III beach
Exceptional
(115 reviews)

Your Hawaiian Beach Get Away, Steps From Great Beach!

Kihei

12% off
$231
$1,616 for 7 nights
All fees included
Your Hawaiian Beach Get Away, Steps From Great Beach!
Lanai view
Exterior
Living area
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.
Spectacular ocean view from this beautiful condo lanai
Maui Tropical Plantation
Golfing on Maui is one of the best
Kitchen, living area to lanai
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!
Dining
Property grounds
view from lanai over the complex grounds
Living area
Exceptional
(165 reviews)

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

Kihei

8% off
$360
$2,523 for 7 nights
All fees included
Kamaole Sands Remodeled 1 Bed 2 bathroom, Split AC, king bed
Room
Room
Interior
Exterior
Exceptional
(51 reviews)

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

Kihei

8% off
$218
$1,527 for 7 nights
All fees included
Blue Sky Escapes One bedroom Beach Steps Away! Pool Hot tub
Exterior detail
Living area
Outdoor dining
Amazing pool, hot tub, and BBQ amenities
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
Living area
Outdoor dining
Pool
Interior
Exceptional
(31 reviews)

Kihei Getaway in Paradise

Kihei

8% off
$389
$2,724 for 7 nights
All fees included
Kihei Getaway in Paradise
  • 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.