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Compare Villas in Olowalu with updated reviews, rates, and availability.

Gated 2-story beach house with big yard

10.0 out of 10, Exceptional, (47)
"Ideal location for beach and ocean lovers! Beach is only 2 minutes away. 30 minutes to other Maui destinations like Lahaina and Road to Hana.Home was beautifully decorated and nice layout. Two twin beds upstairs have a low ceiling so tall people may feel tight. Our family would definitely return to this home rental."
Gated 2-story beach house with big yard

Eco friendly modern home, gorgeous Ocean & Mt view, Indoor outdoor living

10.0 out of 10, Exceptional, (159)
"Secluded and private with a wonderful view and with everything one could ask for to feel at home Upcountry. The owner was very helpful whenever needed. Thanks for the great stay! Looking forward to our return."
The price is AED 2,332
AED 4,562 total
includes taxes & fees
14 Mar - 15 Mar
Eco friendly modern home, gorgeous Ocean & Mt view, Indoor outdoor living

EXCEPTIONAL, PRIVATE, DIRECT OCEAN FRONT VILLA! Wailea Beach Villa B102

10.0 out of 10, Exceptional, (25)
"Positive"
EXCEPTIONAL, PRIVATE, DIRECT OCEAN FRONT VILLA! Wailea Beach Villa B102

Stunning Ocean View at Kapalua Bay Villas

10.0 out of 10, Exceptional, (56)
"Great view. Wonderful place. Lots of fun."
Stunning Ocean View at Kapalua Bay Villas

~ This Is Wailea Living ~

10.0 out of 10, Exceptional, (118)
"We (wife, daughter and I) stayed two weeks. The place is as described… updated, clean and quiet. We enjoyed everything about the area including the closeness to retail shops, golf and grocery stores. Chris was an excellent host. His communications were spot on and he went above and beyond by sharing thoughts on a storm that blew in on our second day. I would not hesitate to stay here in the future. "
~ This Is Wailea Living ~

Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-4

9.6 out of 10, Exceptional, (67)
"Beautiful villa with all of the accommodations needed for a wonderful holiday. Perfectly located to get to all that Wailea offers."
Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-4

RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS

10.0 out of 10, Exceptional, (184)
"This house and location was amazing. Beach access any time of day, and usually solitude. Kids had a great time in the pool when not in the ocean. Property manager was very communicative, we had no complaints. Will book again!"
RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS

Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere

10.0 out of 10, Exceptional, (70)
"Linda’s place is beautiful! The location is great, and the condo is big, with 2 master suites plus another bedroom this condo is the perfect layout for 2 couples/ family’s. Big beautiful deck with a bbq. We loved staying there and would forsure book again! "
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere

Hula On In to Beach House Chic Style, Click the Video tour below!

10.0 out of 10, Exceptional, (129)
"We loved the condo! Really cleaning well organized. Great space, location and amenities. It has everything you need for a great get away. Groceries, restaurants and beautiful all within 5 min. Thank you for your home away from home."
Hula On In to Beach House Chic Style, Click the Video tour below!

Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei

10.0 out of 10, Exceptional, (53)
"My family and I planned this trip back in March 2024 and reserved this property in Ho'olei.Right from the initial reservation process and first payment installment, the interaction with Matthew was excellent and seamless. Matthew was responsive and very helpful.The unit at Ho'olei was remarkable, well located within the property, and most importantly, was extremely clean when we checked in. There was a small welcome gift which was appreciative. The unit was very well equipped with all we needed,...
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei

CLEAN, GREAT LOCATION, PRIVATE, Vaulted Ceilings, Lots of amenities, Oceanview!

9.6 out of 10, Exceptional, (64)
"Great stay at Tamara's condo. The location is fantastic, walking distance to the beach, shops, restaurants and the Wailea beach trail. The condo was well equipped. We easily cooked meals in the kitchen, which had everything we needed. The condo was clean and welcoming. We brought the provided beach chairs and beach towels, to Big Beach. The bathroom had sunscreen and a first aid kit, The band aids came in handy. Having a laundry allowed us to pack light. We really appreciated that Tamara left...
CLEAN, GREAT LOCATION, PRIVATE, Vaulted Ceilings, Lots of amenities, Oceanview!

Spectacular 3rd Row Villa at Ho'olei with Ocean Views

10.0 out of 10, Exceptional, (54)
"We had an amazing time. Will be coming back again! "
Spectacular 3rd Row Villa at Ho'olei with Ocean Views

OCEANFRONT gated Kapalua Bay Villa 23G1. Steps to beach!

9.8 out of 10, Exceptional, (53)
"we love this area, home was awesome can’t wait to get back to Maui!!"
The price is AED 944
AED 3,495 total
includes taxes & fees
22 Mar - 23 Mar
OCEANFRONT gated Kapalua Bay Villa 23G1. Steps to beach!

Spectacular Ka'anapali Villa 3/3, AC, pool, Ocean and Island views

9.8 out of 10, Exceptional, (50)
"Enough space for both my kiddos to stretch out and an amazing view from both lanais. We had a minor issue with the oven the first night and they had maintenance come first thing the next morning to fix the issue. We can't wait to go back to the island. "
Spectacular Ka'anapali Villa 3/3, AC, pool, Ocean and Island views

Marriott's Maui Ocean Club, Lāhainā (2BR)

The price is AED 3,669
AED 4,215 total
includes taxes & fees
13 Mar - 14 Mar
Marriott's Maui Ocean Club, Lāhainā (2BR)

OCEANVIEW, 1 bed/1 bath condo at the exclusive gated Kapalua Bay Villa 32G4!

9.8 out of 10, Exceptional, (44)
"wonderful, relaxing near privacy - not front row yet calming"
The price is AED 944
AED 3,495 total
includes taxes & fees
21 Mar - 22 Mar
OCEANVIEW, 1 bed/1 bath condo at the exclusive gated Kapalua Bay Villa 32G4!

WHITE LOTUS🏝️ Brand New Euro Luxury 3BR 3BTH Golf Villa, Steps to Beach & 4th Tee

10.0 out of 10, Exceptional, (20)
"family vacation at the this February was exceptional. Easy access to Kapalua Bay. Positioned ideally, the villa offered stunning views of the ocean, golf course, and mountains. The host was friendly, attentive, and provided convenient amenities that ensured our comfort throughout the trip. Top-choice destination for our family, highly recommend it to those seeking a serene and fulfilling Maui escape."
WHITE LOTUS🏝️ Brand New Euro Luxury 3BR 3BTH Golf Villa, Steps to Beach & 4th Tee

One of our best! (3/27- 4/6) Open ~ Must See OCEAN FRONT Villa ~ March & April Availability

10.0 out of 10, Exceptional, (67)
"We thoroughly enjoyed our stay at this beautiful villa. We usually stay at The Ritz, however, this was very nearby and allowed us the best of both properties and then some!"
One of our best! (3/27- 4/6) Open ~ Must See OCEAN FRONT Villa ~ March & April Availability

5 Star Ocean View, Beach House Chic, Click the Video tour below!

10.0 out of 10, Exceptional, (85)
"While I would love to keep this property my little secret, that wouldn’t be fair. Absolutely excellent property, quality, cleanliness, communication and location. Wonderfully supplied kitchen and activities items. WiFi great, TV selections very good. I would select this property everytime. Owners were super friendly and communicative. Thank you!!"
5 Star Ocean View, Beach House Chic, Click the Video tour below!

Luana Villa 7B at Honua Kai w/ Private BBQ & Lanai ~ Ground-Floor Maui Paradise

10.0 out of 10, Exceptional, (12)
"Party of 6, including teenagers and elders, above age 70. My husband and I, early 50s, had an amazingly relaxing vacation!"
Luana Villa 7B at Honua Kai w/ Private BBQ & Lanai ~ Ground-Floor Maui Paradise
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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Other property types in Olowalu

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3479)
"Thank you! Loved it!"
The price is AED 918
AED 1,191 total
includes taxes & fees
14 Mar - 15 Mar
Aston Kaanapali Shores

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2718)
"Great location. Easy access to multiple pools and beach. Outstanding for family. "
The price is AED 1,216
AED 3,380 total
includes taxes & fees
4 Apr - 5 Apr
OUTRIGGER Honua Kai Resort & Spa

Aston Maui Kaanapali Villas

3.0 star property
8.6 out of 10, Excellent, (2359)
"It's a beautiful location, near easily walkable spots and perfect for people with small children. The pool could be bigger, but if you have a child younger than 3 years old, it's a perfect size. Lots of other wonderful guests to hang out with."
The price is AED 900
AED 1,386 total
includes taxes & fees
12 Mar - 13 Mar
Aston Maui Kaanapali Villas
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.

Frequently asked questions

How much do villas in Olowalu cost?
Prices for villas in Olowalu range between and per night. Whatever your budget, you’ll find someplace that fits the bill on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Olowalu?
Pick from villas in Olowalu. Whether you’re vacationing with the family or planning a weekend escape with your buddies, Expedia will help you find the perfect space for your entire crew.
Why book your villa in Olowalu with Expedia?
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How can I find cheap villas in Olowalu?
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