South Maui holiday homes

We found 5,171 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – South Maui

Showing deals for:18 Dec - 25 Dec

Living area
Outdoor dining
Pool
Exterior
Exceptional
(177 reviews)

Remodeled Quiet Oceanfront Corner Unit on 3rd Floor at Sugar Beach Resort

Kihei

7% off
NZ$5,003
for 7 nights, 1 apartment
NZ$715 per night
includes taxes & fees
Remodeled Quiet Oceanfront Corner Unit on 3rd Floor at Sugar Beach Resort
Freds South Shore Cantina.. Terrific Taco Tuesday Specials!! Sunsets are GREAT
Surrounded by lush tropical scenery and serenity! Small Peek-a-Boo View
Kitchen fully updated
Living area to kitchen and entry
Excellent
(92 reviews)

Privacy in Paradise! 2nd Flr, updated,across from Beach! Smaller 6 unit complex

Kihei

7% off
NZ$4,550
for 7 nights, 1 apartment
NZ$650 per night
includes taxes & fees
Privacy in Paradise! 2nd Flr, updated,across from Beach! Smaller 6 unit complex
Dining area, kitchen
Granite countertop, living area
Living area looks out to lanai and lush landscaping
Living area, dining, and kitchen
Exceptional
(140 reviews)

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

Kihei

7% off
NZ$3,528
for 7 nights, 1 apartment
NZ$504 per night
includes taxes & fees
Kihei, Maui Ground Floor Tropical Getaway - Across street from beach
Living area with beautiful views from the lanai
Try your golf game and one of Maui's terrific Golf Courses
Beautiful Lanai view
Experience the Hawaiian Culture at the Luau while on island. Concierge Available
Wonderful
(22 reviews)

Pool View from the 2nd floor with the Great Values this Season!!

Kihei

7% off
NZ$3,655
for 7 nights, 1 apartment
NZ$522 per night
includes taxes & fees
Pool View from the 2nd floor with the Great Values this Season!!
2023 new sofa bed living room
Living area
Lanai with Table and 4 Chairs Ocean View
Pool Area
Exceptional
(42 reviews)

Modern, remodeled, ocean views, comfortable and convenient 580 sf

Kihei

7% off
NZ$4,375
for 7 nights, 1 apartment
NZ$625 per night
includes taxes & fees
Modern, remodeled, ocean views, comfortable and convenient 580 sf
Private kitchen
Property grounds
Dining
Living area
Exceptional
(168 reviews)

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

Kihei

7% off
NZ$8,624
for 7 nights, 1 apartment
NZ$1,232 per night
includes taxes & fees
Kamaole Sands Remodeled 1 Bed 2 bathroom, Split AC, king bed
View from the lanai at sunset
Grand Champions Entrance with Waterfall feature
Entrance to the condo
Renovated kitchen with built in bar
Exceptional
(110 reviews)

Escape to Paradise – Your Dream Wailea Getaway Awaits!

Kihei

7% off
NZ$8,436
for 7 nights, 1 apartment
NZ$1,205 per night
includes taxes & fees
Escape to Paradise – Your Dream Wailea Getaway Awaits!
Living Room from Master Bedroom Railing
Lower Swimming Pool
Living Room
New Kitchen
Exceptional
(95 reviews)

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

Kihei

5% off
NZ$6,201
for 7 nights, 1 apartment
NZ$886 per night
includes taxes & fees
D211 Quiet & Private 2br2ba near Wailea 2026 Discount 10% 7 nts or more.
Interior
Pool
Private kitchen
Terrace/patio
Exceptional
(143 reviews)

Luxurious 1 BR, 2 BA Wailea- Remodeled Bathrooms.

Kihei

7% off
NZ$6,414
for 7 nights, 1 apartment
NZ$916 per night
includes taxes & fees
Luxurious 1 BR, 2 BA Wailea- Remodeled Bathrooms.
Our 3 turtles welcome you
Living area
Dresser Drawers in bedroom. AC cabinet to the right of TV.
Interior
Exceptional
(50 reviews)

Beachfront 1-bedroom corner condo on Kameole Beach II, with two ocean views.

Kihei

7% off
NZ$7,066
for 7 nights, 1 apartment
NZ$1,009 per night
includes taxes & fees
Beachfront 1-bedroom corner condo on Kameole Beach II, with two ocean views.
Property grounds
Pool
Outdoor dining
Interior
Exceptional
(175 reviews)

Tropical garden setting minutes from the beach! Not a high rise!

Kihei

7% off
NZ$3,491
for 7 nights, 1 apartment
NZ$499 per night
includes taxes & fees
Tropical garden setting minutes from the beach! Not a high rise!
Private kitchen
Outdoor dining
Room
The villa is nestled in the middle of world class golf courses
Exceptional
(71 reviews)

Luxury Wailea Villa l Remodeled l Perfect for Couples l Only 5 Star Reviews

Kihei

7% off
NZ$8,924
for 7 nights, 1 apartment
NZ$1,275 per night
includes taxes & fees
Luxury Wailea Villa l Remodeled l Perfect for Couples l Only 5 Star Reviews
Private kitchen
Living area
Outdoor dining
Exterior detail
Exceptional
(126 reviews)

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

Kihei

8% off
NZ$14,822
for 7 nights, 1 apartment
NZ$2,117 per night
includes taxes & fees
Artistic Top-Floor Tropical Penthouse – Steps to Maui’s Best Beach
Rest and rejuvenate
Property grounds
60 foot "L"-shaped Swimming Pool 81-84ºF  & Hot Tub 102ºF all year long
Pool and hot tub are nestled behind greenery on our lush 5.5 acres
Exceptional
(144 reviews)

🌺Lush Oceanfront Penthouse with Pool, Hot Tub, Mountain Sunrises, Ocean Sunsets

Kihei

7% off
NZ$6,058
for 7 nights, 1 apartment
NZ$865 per night
includes taxes & fees
🌺Lush Oceanfront Penthouse with Pool, Hot Tub, Mountain Sunrises, Ocean Sunsets
Kitchen
Clubhouse pool and hot tub
Common Garden area
Kitchen bar view
Exceptional
(10 reviews)

Fully Remodeled Modern Island Style!

Kihei

7% off
NZ$13,312
for 7 nights, 1 apartment
NZ$1,902 per night
includes taxes & fees
Fully Remodeled Modern Island Style!
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

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

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your South Maui getaway

Learn about the unique charm of South Maui with a stay in a holiday home rental. This city has something for everyone. Wailea Beach and Haleakala National Park are just a couple of the must-see attractions in the area. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in South Maui

Are you hoping to find attractions to visit while you're in the area? Venture out of your cosy holiday rental and experience everything that makes South Maui a one-of-a-kind holiday spot. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Wailea Blue Golf Course (1.5 mi / 2.4 km)
  • Wailea Emerald Golf Course (2.1 mi / 3.3 km)
  • Wailea Gold Golf Course (2.1 mi / 3.4 km)
  • Maui Nui Golf Club (3.7 mi / 6 km)
  • Maui Spa Retreat (12.6 mi / 20.2 km)
  • Kaanapali Golf Courses (22.5 mi / 36.3 km)

Exploring the natural landscape of South Maui

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, South Maui is a great place to spend some time outside. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Kaanapali Beach (22.8 mi / 36.7 km)
  • Wailea Beach (1.1 mi / 1.8 km)
  • Haleakala National Park (17.8 mi / 28.7 km)
  • Ulua Beach (0.7 mi / 1.1 km)
  • Keawakapu Beach North (0.9 mi / 1.4 km)
  • Kamaole Beach Park 3 (1.4 mi / 2.2 km)

Frequently asked questions

What is the best area to stay in South Maui when booking a holiday home?
Wailea is among the most well-liked locations to book a holiday home in South Maui. Searching for some awesome things to do in this destination? Take time to visit Wailea Beach and Keawakapu Beach North.
What is the most popular type of holiday home accommodation in South Maui?
Condos are the most popular kind of holiday home in South Maui, according to our data. Even if you have something a little different in mind, Bookabach has properties in loads of shapes and sizes. Take a look at our options to find your perfect pad.
How much does it cost to rent a holiday home in South Maui?
Several things influence how much you pay for a holiday home in South Maui, including the time of year, length of stay and property type. Still, all of our holiday homes have something in common — amazing value. Simply enter your travel dates to find your ideal match.
How much does it cost to rent a beach house in South Maui?
The average price for a holiday home near the beach in South Maui depends on when you're visiting the area and the size and style of property you're searching for. You can find prices easily and quickly on Bookabach by entering your travel dates. Then use our filter tool to select the number of bedrooms and amenities that you need, like a pool, air conditioning and WiFi.
What are popular home amenities in South Maui?
Some of the most popular home amenities people are searching for in South Maui are a stovetop, a microwave oven and a fridge. Whether you're on a trip with your besties, family or even pets, Bookabach holiday homes include the best amenities for beginning new traditions with the people that matter most.
Are there large group holiday homes in South Maui?
With 35 holiday homes that can host 10 or more guests in South Maui, you won't have to keep anyone off the invite list. From family holidays to special events like Christmas and birthday parties, Bookabach will help you find a large group home to suit the occasion.
What are the top attractions for families in South Maui?
You'll find lots of amazing things to do and see with the family in South Maui, such as:
  • Wailea Beach
  • Makena State Park Beach
  • Kamaole Beach Park
Can I find two-bedroom holiday homes in South Maui?
South Maui has 1,580 two-bedroom properties for you to select from. Experience a holiday home with all the privacy and comfort you need at an attractive price on Bookabach.
Are there holiday homes with WiFi in South Maui?
Whether you'd like to stay in touch with world events, send a few emails or post a pic to social media, there are 1,979 holiday homes with WiFi in South Maui. Check the "WiFi" box when searching on Bookabach and stay connected on your getaway.
How old do you have to be to rent a holiday home in South Maui?
The minimum required age is generally 16, 18 or 21. It can differ from one property to another on Bookabach, so look at the rules of your chosen South Maui stay before booking your trip.
How long can I rent a holiday home in South Maui for?
How long you can rent a holiday home in South Maui differs according to the property. Simply enter your chosen travel dates to look at a list of options offering extended stays. With plenty of creature comforts such as laundries and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to get somewhere just right to call your home away from home in South Maui.

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