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Search Olowalu Villa Rentals from CA $398

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Check prices for these dates

Next weekend
Apr 18 - Apr 20
In two weeks
Apr 25 - Apr 27
In one month
May 9 - May 11
In two months
Jun 6 - Jun 8

Browse Select Olowalu Villas

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

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

9.8 out of 10, Exceptional, (55)
"Great location- quiet at night, super clean, very comfortable bed, loved the roomy shower! We loved having coffee along outside on the patio while watching for whales. Don't forget your binoculars! It was lovely to use the folding chairs supplied when we walked over to Kapalua Bay beach to snorkel and swim. We also loved being able to walk to the shops/restaurants/walking trails near the Ritz. Nice to make some of our own meals along with dining out. We had a wonderful stay and plan to...
The price is CA $398
CA $1,424 total
includes taxes & fees
May 9 - May 10
OCEANFRONT gated Kapalua Bay Villa 23G1. Steps to beach!
Mar- May special rates. Eco friendly modern home, gorgeous Ocean & Mt views
Fridge, microwave, oven, stovetop

Mar- May special rates. Eco friendly modern home, gorgeous Ocean & Mt views

10.0 out of 10, Exceptional, (163)
"The home itself is a sanctuary and was hard to leave daily as we went out and explored the island but always looked forward to it in the evening. The mornings were equally amazing. Host was easy to get in touch with and answered questions quickly. Will definitely seek it out again when we return"
The price is CA $641
CA $1,419 total
includes taxes & fees
Apr 12 - Apr 13
Mar- May special rates. Eco friendly modern home, gorgeous Ocean & Mt views
~ This Is Wailea Living ~
Point of interest

~ This Is Wailea Living ~

10.0 out of 10, Exceptional, (120)
"We really enjoyed our stay in this condo. It was clean and the primary bed was very comfortable. Communication with the host was smooth and efficient. The AC worked great. Beach/pool towels and portable chairs were provided, which was great. As a note, though, I would have really appreciated a cooler and umbrella for the beach. I’d definitely recommend this place to a couple or small family. "
~ This Is Wailea Living ~
Hula On In to Beach House Chic Style, Click the Video tour below!
Outdoor pool

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!
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
Outdoor pool, an infinity pool

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

10.0 out of 10, Exceptional, (72)
"We felt so removed from all the hustle bustle of daily life. Our villa was amazing. It had everything we needed and more. We all had such a good time. "
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
Private Ocean Front at Wailea Beach Villas B102
Pool

Private Ocean Front at Wailea Beach Villas B102

10.0 out of 10, Exceptional, (25)
"Positive"
Private Ocean Front at Wailea Beach Villas B102
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei
Pool

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
May is a Great Time to Play on Maui ~ NICE OCEAN FRONT Villa ~ Newer AC ~ Platinum Maui Vacations
Pool

May is a Great Time to Play on Maui ~ NICE OCEAN FRONT Villa ~ Newer AC ~ Platinum Maui Vacations

10.0 out of 10, Exceptional, (56)
"We found this unit comfortable and well outfitted for our needs. Enjoyed the views over the water and walking the trail.along the water's edge. Spectacular. Easy access to good restaurants too!"
The price is CA $512
CA $1,082 total
includes taxes & fees
Apr 20 - Apr 21
May is a Great Time to Play on Maui ~ NICE OCEAN FRONT Villa ~ Newer AC ~ Platinum Maui Vacations
MODERN HAWAII ⛳️ Luxe Remodel, Closest 3BR Kapalua Golf Villa to Beach & 4th Tee!
Beach nearby

MODERN HAWAII ⛳️ Luxe Remodel, Closest 3BR Kapalua Golf Villa to Beach & 4th Tee!

10.0 out of 10, Exceptional, (62)
"This is the second time we have stayed at this property. In a place as beautiful as Maui, with so much to explore, that says a lot. It’s an absolutely perfect location with beautiful views, a stunning interior, and an attentive and fabulous host who was both responsive and accommodating. Everything you need is here—especially if you love to cook—but you are also by so many fantastic restaurants if want to explore. Perfect for families and groups. Every inch of this unit is gorgeous, down to the...
MODERN HAWAII ⛳️ Luxe Remodel, Closest 3BR Kapalua Golf Villa to Beach & 4th Tee!
Exquisite Oceanview Villa with Resort Amenities in Gated Community
Pool

Exquisite Oceanview Villa with Resort Amenities in Gated Community

10.0 out of 10, Exceptional, (62)
"Property is greatView great "
Exquisite Oceanview Villa with Resort Amenities in Gated Community
Maui Resort Rentals: Luana Garden Villas 8C – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
Pool

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

9.8 out of 10, Exceptional, (8)
"We really enjoyed our stay at Luana Garden Villas. The villa was very clean and well equipped for a great stay for my family. Beds were comfortable, fixtures were beautiful, and the covered lanai with sliding doors was amazing! Close to the beach with a great boardwalk or just a couple steps away from the pools. We had everything we needed for a great vacation."
Maui Resort Rentals: Luana Garden Villas 8C – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
Gated 2-story beach house with big yard
Exterior detail

Gated 2-story beach house with big yard

10.0 out of 10, Exceptional, (51)
"Our family of 6 thoroughly enjoyed this house. Situated within walking distance of a great beach and close to plenty of shopping, you couldn’t ask for a better location. The property is fenced in which allows for privacy and a sense of security. There are plenty of amenities in the house including surfboards, boogie boards, chairs and an umbrella for the beach, bikes a ping pong table, a hammock and much more. We had a great time and would stay there again in a heartbeat!"
Gated 2-story beach house with big yard
RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS
Exterior

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

10.0 out of 10, Exceptional, (186)
"Amazing family vacation!"
RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS
Marriott's Maui Ocean Club, Lāhainā (2BR)
A heated pool

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

2.0 out of 10, (1)
The price is CA $1,423
CA $1,634 total
includes taxes & fees
Apr 13 - Apr 14
Marriott's Maui Ocean Club, Lāhainā (2BR)
WHITE LOTUS🏝️ Brand New Bespoke Euro Luxury 3BR 3BTH Golf Villa, Steps to Beach
Sun loungers, beach towels

WHITE LOTUS🏝️ Brand New Bespoke Euro Luxury 3BR 3BTH Golf Villa, Steps to Beach

10.0 out of 10, Exceptional, (24)
"it was a great condo, all the new amenities, one of the most largest amenities in the area. Feel fortunate that we were able to stay there. Anyone goes to this location? Will definitely enjoy themselves."
WHITE LOTUS🏝️ Brand New Bespoke Euro Luxury 3BR 3BTH Golf Villa, Steps to Beach
One of our best ON SALE & Wide Open (4/16- 5/8) ~ Must See OCEAN FRONT Villa ~
Outdoor dining

One of our best ON SALE & Wide Open (4/16- 5/8) ~ Must See OCEAN FRONT Villa ~

10.0 out of 10, Exceptional, (68)
"Loved it! Beautiful view!!!"
One of our best ON SALE & Wide Open (4/16- 5/8) ~ Must See OCEAN FRONT Villa ~
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!
A waterfall pool

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

9.6 out of 10, Exceptional, (53)
"Overall this property was perfect. Had everything we needed for our family vacation (6 adults, 3 children). Property was clean, located close to pool and beach, shopping close by, we’d definitely stay here again in the future. "
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!
Stunning Ocean View at Kapalua Bay Villas
Outdoor dining

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
Luana Villa 7B at Honua Kai w/ Private BBQ & Lanai ~ Ground-Floor Maui Paradise
Outdoor pool, a heated pool

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
Honeymooner's Delight, Private Pool & Property,Ocean Views, close to beach.
Outdoor pool

Honeymooner's Delight, Private Pool & Property,Ocean Views, close to beach.

9.8 out of 10, Exceptional, (55)
"Absolutely stunning property. Private pool, love birds and other birds galore. Property is as listed. Watch the whales from the pool deck. We hung out at the pool all the time. Totally private. Terri was wonderful to work with. She kept in touch during our stay. She also stocked our suite with bananas, mango and other treats. The outside shower is to die for. "
Honeymooner's Delight, Private Pool & Property,Ocean Views, close to beach.
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 Maui Kaanapali Villas
Exterior

Aston Maui Kaanapali Villas

3.0 star property
8.6 out of 10, Excellent, (2380)
"This is my 2nd time staying here was a great overall experience. Room was clean no bugs or little critters. Kitchen makes it easy to make your own meals to save money. Will definitely stay here again highly recommend "
The price is CA $304
CA $485 total
includes taxes & fees
Apr 15 - Apr 16
Aston Maui Kaanapali Villas
Aston Kaanapali Shores
2 outdoor pools, pool umbrellas, sun loungers

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3525)
"This property has a great pool and garden area. The kid pool has the most character and shade. We loved how the birds came in to roost in the garden at night and filled the air with their evening “talking.” Room was clean, spacious and had good AC. We were pleasantly surprised by the excellent value in the menu offerings at the Beach Club restaurant as well as the good view of the ocean. This property does not have much beach in front of it, but a short way down the boardwalk you can access the...
The price is CA $310
CA $408 total
includes taxes & fees
Apr 13 - Apr 14
Aston Kaanapali Shores
Sands of Kahana 354
Condo, Multiple Beds (Sands of Kahana 354) | Beach/ocean view

Sands of Kahana 354

4.0 star property
Sands of Kahana 354
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 CA $398 and CA $1,423 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 363 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?
Use Expedia to find your dream villa in Olowalu. Traveling with the kids? Make the most of our filters to look for stays with a kitchen or a pool. If you have a certain budget, choose how much you want to spend and your preferred star rating. We’ll help you find a perfect place that suits your style and taste.
How can I find cheap villas in Olowalu?
With Expedia’s helpful filter tool, sourcing cheap villas in Olowalu couldn’t be easier. To discover accommodations that won’t break the bank, fine-tune your search by budget, amenities and star rating.