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Olowalu Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Olowalu holiday rentals

Blackout curtains, iron/ironing board, free WiFi
The Ocean View Residence

The Ocean View Residence

The Ocean View Residence
3.0 star property
South Kihei
10.0 out of 10, Exceptional, (1)
"Very nice condo for a longer-term stay. We loved being able to cook. "
United States
John
The price is HK$1,792
HK$7,013 total
includes taxes & fees
29 Dec - 30 Dec
The Ocean View Residence
Exterior
Signature Residences at Maui Banyan

Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
4.5 star property
South Kihei
9.6 out of 10, Exceptional, (4)
"Wonderful experience. Clean, convenient, great location, pool, hot tub, beautiful property, and safe. Had a great time."
United States
Melinda
The price is HK$617
HK$4,548 total
includes taxes & fees
1 Jan - 2 Jan 2026
Signature Residences at Maui Banyan
Beach towels
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
Kuau
9.4 out of 10, Exceptional, (196)
"Very quiet safe place. "
Canada
Monica
The price is HK$1,438
HK$3,416 total
includes taxes & fees
7 Jan - 8 Jan 2026
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
Exterior
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
North Kihei
10.0 out of 10, Exceptional, (267)
"Great stay"
United States
Noah C.
The price is HK$762
HK$3,046 total
includes taxes & fees
9 Jan - 10 Jan 2026
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
Exterior
Kuau Surf 2.0 Maui North Shore Locally-Owned

Kuau Surf 2.0 Maui North Shore Locally-Owned

Kuau Surf 2.0 Maui North Shore Locally-Owned
Paia
9.2 out of 10, Wonderful, (19)
"Clean and convenient"
United States
Ilya L
The price is HK$1,710
HK$2,931 total
includes taxes & fees
22 Jan - 23 Jan 2026
Kuau Surf 2.0 Maui North Shore Locally-Owned
4 outdoor pools, open 8:00 AM to 10:00 PM, pool cabanas (surcharge)
OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.0 star property
Lahaina
8.8 out of 10, Excellent, (2887)
"Wonderful stay! "
United States
Quiauna
The price is HK$3,164
HK$7,896 total
includes taxes & fees
15 Jan - 16 Jan 2026
OUTRIGGER Honua Kai Resort & Spa
Outdoor dining
Oceanfront penthouse with amazing views at Kauhale Makai

Oceanfront penthouse with amazing views at Kauhale Makai

Oceanfront penthouse with amazing views at Kauhale Makai
Central Kihei
9.8 out of 10, Exceptional, (74)
"This was our first stay in Kihei and we had a wonderful time! The location was great and we appreciated the quietness of our space. We were able to walk to a nearby shopping plaza where we found delicious food and coffee. Our host was kind and communicated promptly and efficiently. We will be back! "
United States
Paige O.
The price is HK$987
HK$4,225 total
includes taxes & fees
26 Jan - 27 Jan 2026
Oceanfront penthouse with amazing views at Kauhale Makai
Beach nearby, white sand, beach towels
Napili Village Hotel

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (145)
"Exactly what we were looking for! Close walking distance to beach and dining!"
United States
Tessa
The price is HK$2,229
HK$2,647 total
includes taxes & fees
19 Jan - 20 Jan 2026
Napili Village Hotel
Exterior
Aston Kaanapali Shores

Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (3929)
"Loved the 2 pools and 2 hot tub, staff is great…thank you!"
United States
Candida
The price is HK$2,228
HK$2,874 total
includes taxes & fees
1 Jan - 2 Jan 2026
Aston Kaanapali Shores
Exterior
Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Lahaina
8.8 out of 10, Excellent, (2522)
"We enjoyed the property "
United States
Therese
The price is HK$2,448
HK$3,593 total
includes taxes & fees
1 Jan - 2 Jan 2026
Aston Maui Kaanapali Villas
Aerial view
Kuleana Club - 306

Kuleana Club - 306

Kuleana Club - 306
3.0 star property
Lahaina
The price is HK$2,168
HK$5,783 total
includes taxes & fees
8 Jan - 9 Jan 2026
Kuleana Club - 306
Exterior
The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (329)
"Amazing resort second time being here will definitely be back next year "
United States
David
The price is HK$2,591
HK$5,917 total
includes taxes & fees
27 Jan - 28 Jan 2026
The Whaler Resort Kaanapali Beach
Property grounds
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC

OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC

OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC
Wailuku
9.6 out of 10, Exceptional, (160)
"Everything was great. Kitchen well stocked, beautiful view. "
United States
Eric S.
The price is HK$1,935
HK$4,251 total
includes taxes & fees
24 Jan - 25 Jan 2026
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC
Property grounds
This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!

This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!

This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!
North Kihei
10.0 out of 10, Exceptional, (31)
"we really enjoyed our stay here. It is clean and maintained well and close to the beach."
United States
stuti s.
The price is HK$1,034
HK$3,562 total
includes taxes & fees
29 Dec - 30 Dec
This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!
Property grounds
Enjoy Ocean Views From Lanai, Living room & Bedroom, Beachfront Pool!

Enjoy Ocean Views From Lanai, Living room & Bedroom, Beachfront Pool!

Enjoy Ocean Views From Lanai, Living room & Bedroom, Beachfront Pool!
Central Kihei
9.4 out of 10, Exceptional, (84)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Beautiful condo, great views and location"
United States
Pam B.
The price is HK$1,213
HK$4,500 total
includes taxes & fees
12 Jan - 13 Jan 2026
Enjoy Ocean Views From Lanai, Living room & Bedroom, Beachfront Pool!
Exterior
Oceanfront condo with pool & balcony - walk to dining, activities, and more

Oceanfront condo with pool & balcony - walk to dining, activities, and more

Oceanfront condo with pool & balcony - walk to dining, activities, and more
Wailuku
9.4 out of 10, Exceptional, (131)
"The view is amazing"
United States
Carlos A.
The price is HK$1,804
HK$5,290 total
includes taxes & fees
19 Jan - 20 Jan 2026
Oceanfront condo with pool & balcony - walk to dining, activities, and more
Beach nearby, sun-loungers, beach towels
Pacific Shores 2bd 2bth Kihei MAUI Condo Kamaole Beach HAWAII Vacation Rental

Pacific Shores 2bd 2bth Kihei MAUI Condo Kamaole Beach HAWAII Vacation Rental

Pacific Shores 2bd 2bth Kihei MAUI Condo Kamaole Beach HAWAII Vacation Rental
4.0 star property
South Kihei
9.6 out of 10, Exceptional, (48)
"Good location near beach with AC in each room, many beds were good for a larger group."
Canada
Daniel C.
The price is HK$1,546
HK$4,137 total
includes taxes & fees
2 Jan - 3 Jan 2026
Pacific Shores 2bd 2bth Kihei MAUI Condo Kamaole Beach HAWAII Vacation Rental
Pool
Romantic Beachfront Getaway

Romantic Beachfront Getaway

Romantic Beachfront Getaway
Maalaea Bay
9.6 out of 10, Exceptional, (39)
"We were rarely there except to sleep but the apartment has everything we needed. It’s walking distance to the harbor and ocean center. The beach is literally steps outside. The owner was very quickly responsive to our questions."
United States
Amy S.
The price is HK$1,438
HK$3,909 total
includes taxes & fees
1 Jan - 2 Jan 2026
Romantic Beachfront Getaway
A heated pool
Island Sands 401 Oceanfront Condo with Ocean View. Enjoy the saltwater oceanfront swimming pool.

Island Sands 401 Oceanfront Condo with Ocean View. Enjoy the saltwater oceanfront swimming pool.

Island Sands 401 Oceanfront Condo with Ocean View. Enjoy the saltwater oceanfront swimming pool.
Wailuku
9.4 out of 10, Exceptional, (45)
"Island sands is my favorite Condos"
United States
michelle p.
The price is HK$1,127
HK$5,030 total
includes taxes & fees
31 Dec - 1 Jan 2026
Island Sands 401 Oceanfront Condo with Ocean View. Enjoy the saltwater oceanfront swimming pool.
On the beach
Oceanside condo, full kitchen, ocean view. Fully renovated 2023

Oceanside condo, full kitchen, ocean view. Fully renovated 2023

Oceanside condo, full kitchen, ocean view. Fully renovated 2023
Central Kihei
9.4 out of 10, Exceptional, (56)
"Check in was very easy and this is a perfect location for ocean access. "
Canada
Tracy C.
The price is HK$979
HK$2,872 total
includes taxes & fees
4 Jan - 5 Jan 2026
Oceanside condo, full kitchen, ocean view. Fully renovated 2023
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Olowalu Hotel Reviews

Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

10/10 Excellent
"Room was spacious and staff were very helpful."
Lisa 2-night trip
Posted 9 hours ago
Royal Lahaina Resort & Bungalows

Find out more about Olowalu

Search for holiday rentals in Olowalu on Expedia! You can easily find your home rentals, villas, holiday apartments in Olowalu using one of the methods below:

  • View our selection of featured holiday rentals in Olowalu
  • Use the map to find apartments and other holiday homes in the Olowalu neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Olowalu while they last

Look no further and take a look at our great range of rental properties in Olowalu!

Frequently asked questions

Are there holiday rentals in Olowalu?

Yes, there are holiday rentals close to the most popular sights in Olowalu, or you can select a more secluded option if you're looking for a relaxing stay. Olowalu is known for its shopping and restaurants. Make sure you have time to check out the beaches while you're in the area.

What are some of the best holiday rentals that Olowalu has to offer?

Kaiholo Hale: This holiday home rental outside of Olowalu is by the ocean, and equipped with free WiFi and a TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave.

What’s there to see and do in Olowalu?

Explore the area and family-friendly sights such as Hawaiian Islands Humpback Whale National Marine Sanctuary Headquarters, or get out into nature at a spot like Mile Marker 14 Beach. Kaanapali Beach and Wailea Beach are other popular places to visit in the area.

What’s a holiday rental in Olowalu like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Olowalu. Holiday rentals feature extras such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for a small group gathering.