Photo by Claire Houston

Search Olowalu Villa Rentals from CA $2,897

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Browse Select Olowalu Villas

Gated 2-story beach house with big yard

10.0 out of 10, Exceptional, (44)
"The house is amazing, providing the perfect atmosphere for quality time with my family. All slept well, felt at home and enjoyed every moment. Thank you!"
Gated 2-story beach house with big yard

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

Maui Resort Rentals: Hyatt Residence Club – 2BR Oceanfront Middle Floor VIlla

9.6 out of 10, Exceptional, (30)
"Best villa location with views!"
Maui Resort Rentals: Hyatt Residence Club – 2BR Oceanfront Middle Floor VIlla

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

Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!

9.6 out of 10, Exceptional, (49)
"We had a wonderful vacation and this location was perfect. After visiting multiple areas in Maui, we decided we like this area best "
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!

Honua Kai Ground Floor # Luana 1B - 3 bed / 3 bath villa - front side location

10.0 out of 10, Exceptional, (62)
"This is a great location that is quiet but close to the pool and beach. Great for families as we have three boys under the age of 10. We will use this place again for our next stay in Maui."
Honua Kai Ground Floor # Luana 1B - 3 bed / 3 bath villa - front side location

Luxury Kapalua Golf Villa, Prime Location, Minutes to beach, 4 heated pools

10.0 out of 10, Exceptional, (18)
"Our family stayed for 10 days and we had a wonderful time. The condo is beautiful and it was perfect for the six of us.( All adults) We enjoyed delicious coffee every morning on the patio overlooking the golf course and ocean. The amenities are a great bonus. We used the lawn chairs and umbrellas for the beach. We brought our own cooler in our luggage which was a hassle and we did not need to as there are also nice coolers to use. Everything was well thought out. Thanks for an amazing stay! We...
Luxury Kapalua Golf Villa, Prime Location, Minutes to beach, 4 heated pools

FRESH Pricing ~ Spacious, Comfortable & Clean ~ Platinum Maui Vacations

10.0 out of 10, Exceptional, (7)
"I enjoyed my stay and I’ll be back!"
FRESH Pricing ~ Spacious, Comfortable & Clean ~ Platinum Maui Vacations

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

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

9.8 out of 10, Exceptional, (51)
"Overall really enjoyed the property. The pictures were a little misleading in that it looks like there is grass surrounding the lower balcony but it is rock landscaping not grass. Was a little disappointed as we specifically booked the property for the grass area that our baby could crawl on. Besides that we enjoyed the stay and the kapalua area was amazing! Loved the beaches. Was great being so close to the pool"
OCEANFRONT gated Kapalua Bay Villa 23G1. Steps to beach!

Puamana Retreat by Gather: Oceanfront 3BR w/ Lanai & Resort Amenities in Lahain

Puamana Retreat by Gather: Oceanfront 3BR w/ Lanai & Resort Amenities in Lahain

Maui Resort Rentals: Luana Garden Villas 8D – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!

10.0 out of 10, Exceptional, (30)
"Everything about our stay at this property was amazing. Easy check in, great responsiveness from the Host, and the condo was just as great as the pictures. Our family of 8 adults had plenty of room and really enjoyed everything about our rental. "
Maui Resort Rentals: Luana Garden Villas 8D – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!

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

9.8 out of 10, Exceptional, (43)
"wonderful, relaxing near privacy - not front row yet calming"
OCEANVIEW, 1 bed/1 bath condo at the exclusive gated Kapalua Bay Villa 32G4!

One of our best OPEN- 2/16- 2/19 ~ Must See OCEAN FRONT Villa ~ PLATINUM Maui Vacations

10.0 out of 10, Exceptional, (66)
"Excellent location. Gated. Safe. Quiet. "
One of our best OPEN- 2/16- 2/19 ~ Must See OCEAN FRONT Villa ~ PLATINUM Maui Vacations

Luxurious Ocean View Villa at Ho'olei! Experience Hoolei 17-3

10.0 out of 10, Exceptional, (61)
"As advertised, property was lovely and suitable for our family. Beautiful view and very comfortable. "
Luxurious Ocean View Villa at Ho'olei! Experience Hoolei 17-3

Redesigned Penthouse! WBV J106

10.0 out of 10, Exceptional, (64)
"We really enjoyed our stay and were pleased witj the updated unit, condition, and cleanliness. It was plenty of room for our family of 4 adults. Fully stocked chef’s kitchen. The staff is nice and we got a personal on site greeting from the rental manager. Mark at the gate is very friendly. "
Redesigned Penthouse! WBV J106

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

Luxury 3-Bedroom Wailea Beach Villa M312

10.0 out of 10, Exceptional, (9)
"This was the best location, easy to get to beach and mall"
Luxury 3-Bedroom Wailea Beach Villa M312

The Westin Nanea Ocean Villas (3BR)

4.0 out of 10, (2)
"We had booked a 3 bedroom VRBO way in advance for my husband and adult daughter and son. We wanted to stay togerther in one unit. 3 days before we were traveling from the states to Hawaii, we were informed by the host that "the owner was being difficult" and we were not allowed to stay in the unit we booked! They wanted us to cram into a 2 bedroom villa which meant one of the adults would have to sleep on a pull out couch! NOT acceptable. After much discussion, the best they were able to do was...
The price is CA $2,897
CA $3,097 total
includes taxes & fees
Feb 19 - Feb 20
The Westin Nanea Ocean Villas (3BR)

Maui Resort Rentals: 6 Total Bedrooms at Kaanapali’s Newest Luxury Residences, Steps from Beach & Resort Amenities!

Maui Resort Rentals: 6 Total Bedrooms at Kaanapali’s Newest Luxury Residences, Steps from Beach & Resort Amenities!
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, (3444)
"Nice area and walkable to grocery and food trucks.."
The price is CA $580
CA $727 total
includes taxes & fees
Feb 3 - Feb 4
Aston Kaanapali Shores

Kaanapali Alii

4.0 star property
9.6 out of 10, Exceptional, (858)
"Beautiful accommodations."
Kaanapali Alii

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2690)
"Pool area very nice. Close to ocean if wanting a day at the beach too."
The price is CA $543
CA $1,411 total
includes taxes & fees
Feb 2 - Feb 3
OUTRIGGER Honua Kai Resort & Spa
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?
You’ll pay between CA $2,897 and CA $2,897 per night for villas in Olowalu. Whatever your budget, a perfect escape is just a click away 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?
Olowalu has 289 villas to select from. Find the ideal stay quickly and easily by clicking the “Villa” checkbox under the “Property type” tab in our filter tool.
Why book your villa in Olowalu with Expedia?
Booking a villa in Olowalu is as easy as deciding on your travel dates and choosing an option that satisfies your needs. Searching for something upscale or budget friendly, or a property that also comes with a kitchen and laundry? Use Expedia’s search filters to narrow your results and find your dream fit.
How can I find cheap villas in Olowalu?
A wonderful way to get cheap villas in Olowalu is with Expedia’s user-friendly filter tool. Refine your search results by star rating, amenities and budget to secure unbeatable rates in just a few keystrokes.