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Search Olowalu Villa Rentals from CA $937

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Browse Select Olowalu Villas

Gated 2-story beach house with big yard
Exterior detail

Gated 2-story beach house with big yard

10.0 out of 10, Exceptional, (41)
"Reviews I read hinted at how wonderful this place is and it's true and then some. The grounds, furnishings, equipment, kitchen, and everything you would want in a home to be comfortable were there. So many nice touches and if you want to cook some or all of your meals, you will have no problem having everything you need include a BBQ grill. I only wish we had more time to make use of all the house had to offer. The beach is just a three minute walk to the south and two minute walk to the north...
Gated 2-story beach house with big yard
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, (66)
"First trip to Maui - Loved our time at this condo! Thank you Linda! 1. Communication: from the outset, Linda’s communication was outstanding and fast which in my mind is always a good indication. 2. Location: Perfect for the Shops at Wailea and Beach. The condo is adjacent to all the shops in Wailea and you can literally walk from the condo right into all the shops, restaurants, coffee, etc. There is a gate at the condo that connects you right into the shops. The beach is a 2 min walk...
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
Stunning 3BD/4BA Andaz Villa! Huge Private Yard with Pool! Modern Beach Elegance
An infinity pool, a heated pool

Stunning 3BD/4BA Andaz Villa! Huge Private Yard with Pool! Modern Beach Elegance

10.0 out of 10, Exceptional, (2)
"This villa was beautifully decorated, super clean and very convenient yet private and quiet. CB Island vacations was so attentive, and knowing it was my birthday, rewally surprised us at our welcome . Everything was perfect...really. Barbara"
Stunning 3BD/4BA Andaz Villa! Huge Private Yard with Pool! Modern Beach Elegance
Maui Resort Rentals: Marriott's Maui Ocean Club 2 Bedroom Oceanfront Villa
Pool

Maui Resort Rentals: Marriott's Maui Ocean Club 2 Bedroom Oceanfront Villa

10.0 out of 10, Exceptional, (51)
"The Marriott Ocean Club property is centrally located on the west side of Maui. Great beach, pools, and several restaurants and shopping close by. The condo was spacious and perfect for a family. "
Maui Resort Rentals: Marriott's Maui Ocean Club 2 Bedroom Oceanfront Villa
Maui Resort Rentals: Hyatt Residence Club – 2BR Oceanfront Middle Floor VIlla
Pool

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

9.6 out of 10, Exceptional, (27)
"Our accommodations, location, staff, guest services were absolutely amazing!! A "Bucket List" trip for sure!!! "
Maui Resort Rentals: Hyatt Residence Club – 2BR Oceanfront Middle Floor VIlla
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, (50)
"Great for the two of us to sit outside and enjoy the oasis and gorgeous views from everywhere in the condo. "
OCEANFRONT gated Kapalua Bay Villa 23G1. Steps to beach!
OCEANVIEW, 1 bed/1 bath condo at the exclusive gated Kapalua Bay Villa 32G4!
Aerial view

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

9.8 out of 10, Exceptional, (42)
"This was the most relaxing stay in the ideal location. Beautiful home, breathtaking views, and the most comfortable accommodations. It was simple check in process and stress-free. Can’t wait to come back!"
OCEANVIEW, 1 bed/1 bath condo at the exclusive gated Kapalua Bay Villa 32G4!
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, (52)
"Lots of room especially if you are multi family. Having your own bathroom and large kitchen, dining, living room and lanai is wonderful. Pool is amazing, grounds are very well kept. Within walking distance to the Shops of Wailea and Wailea Beach. Have stayed several times before and have never been disappointed!"
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei
Spectacular Ka'anapali Villa 3/3, AC, pool, Ocean and Island views
Beach nearby, beach umbrellas

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

9.8 out of 10, Exceptional, (49)
"Loved staying in this property and the proximity to a great beach with adjacent parking. Appreciated all the beach chairs and snorkel gear that was available to use. Can’t wait to return to paradise! "
Spectacular Ka'anapali Villa 3/3, AC, pool, Ocean and Island views
Maui Resort Rentals: Hyatt Residence Club – 2BR Oceanfront Upper Floor VIlla
An infinity pool

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

10.0 out of 10, Exceptional, (32)
"Facilities were clean and beautiful "
Maui Resort Rentals: Hyatt Residence Club – 2BR Oceanfront Upper Floor VIlla
Maui Resort Rentals: Luana Garden Villas 8D – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
Pool

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

10.0 out of 10, Exceptional, (29)
"Loved our stay. Already planning our next one. Property was amazing and so were the property managers. "
The price is CA $937
CA $3,106 total
includes taxes & fees
Jan 20 - Jan 21, 2025
Maui Resort Rentals: Luana Garden Villas 8D – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-4
Pool

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
Two January Periods Open & Reduced ~ NICE OCEAN FRONT Villa ~ Newer AC ~ Platinum Maui Vacations
Pool

Two January Periods Open & Reduced ~ NICE OCEAN FRONT Villa ~ Newer AC ~ Platinum Maui Vacations

10.0 out of 10, Exceptional, (55)
"Just as described: ocean views, nice pool right out front, updated decor, good space for a couple. We used the barbeque grills at the pool twice, and it was easy. Comfortable bed, roomy master bath. Loved having the Coastal Trail so close for walking. Kapalua is an upscale area with a beautiful beach. Easy to walk to the Montage or Ritz Carlton for their restaurants. "
Two January Periods Open & Reduced ~ NICE OCEAN FRONT Villa ~ Newer AC ~ Platinum Maui Vacations
New Listing! RARE, DIRECT OCEANFRONT Wailea Beach Villa B202
Pool

New Listing! RARE, DIRECT OCEANFRONT Wailea Beach Villa B202

10.0 out of 10, Exceptional, (2)
"Lovely residence. Beautiful views of water and beach."
New Listing! RARE, DIRECT OCEANFRONT Wailea Beach Villa B202
Maui Resort Rentals: Luana Garden Villas 17D – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
Pool

Maui Resort Rentals: Luana Garden Villas 17D – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!

9.8 out of 10, Exceptional, (14)
"This property is Amazing! The pictures do not do it justice. Very spacious and comfortable. Exceeded our expectations."
Maui Resort Rentals: Luana Garden Villas 17D – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
Wailea Beach Villas I503! 3 bedroom 5th floor penthouse!
On the beach

Wailea Beach Villas I503! 3 bedroom 5th floor penthouse!

10.0 out of 10, Exceptional, (73)
"We have stayed in Wailea many times and at this property(not this unit) before as well. It was almost perfect with the exception that my wife would like to see bathrobes . Whatever . It was perfect. "
Wailea Beach Villas I503! 3 bedroom 5th floor penthouse!
I.P.M PRESENTS: VILLA C302 - SPECTACULAR NEW REMODEL + GREAT OCEAN VIEW!
Outdoor pool, an infinity pool

I.P.M PRESENTS: VILLA C302 - SPECTACULAR NEW REMODEL + GREAT OCEAN VIEW!

10.0 out of 10, Exceptional, (8)
"Love Maui...Have vacationed in Maui over 20+ times. This is a Great place to stay. Centrally located to Wailea Shops and restaurants. Enough room for a family of six. Enjoyed our family time together and staying in a beautiful home, in a beautiful area. "
I.P.M PRESENTS: VILLA C302 - SPECTACULAR NEW REMODEL + GREAT OCEAN VIEW!
Maui Resort Rentals: 9 Total Bedrooms at Kaanapali’s Newest Luxury Residences, Steps from Beach & Resort Amenities!
Pool

Maui Resort Rentals: 9 Total Bedrooms at Kaanapali’s Newest Luxury Residences, Steps from Beach & Resort Amenities!

Maui Resort Rentals: 9 Total Bedrooms at Kaanapali’s Newest Luxury Residences, Steps from Beach & Resort Amenities!
Luxurious Ocean View Villa at Ho'olei! Experience Hoolei 17-3
Pool

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

10.0 out of 10, Exceptional, (60)
"A beautiful property with all the amenities you could ever need. "
Luxurious Ocean View Villa at Ho'olei! Experience Hoolei 17-3
Maui Resort Rentals: Hyatt Residence Club – 3BR Oceanfront Upper Floor VIlla
Pool

Maui Resort Rentals: Hyatt Residence Club – 3BR Oceanfront Upper Floor VIlla

9.6 out of 10, Exceptional, (20)
"It was a magical week! The property is beautiful and in an ideal location! Our three bedroom unit allowed us plenty of room and served our family needs perfectly. We will be back!"
Maui Resort Rentals: Hyatt Residence Club – 3BR Oceanfront Upper Floor VIlla
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

OUTRIGGER Honua Kai Resort & Spa
4 outdoor pools, open 8:00 AM to 10:00 PM, cabanas (surcharge)

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2651)
"This place was absolutely amazing! Very clean, friendly staff, spacious and quiet but lively at the same time, amazing balconies with unbelievable views and an overall perfect place to get away! The outdoor areas were clean and inviting- 3 pools and 5 hot tubs. We all loved the food trucks that were within walking distance. Parking was close and easy. Would recommend this place to everyone! It had a condo but resort feel which was super nice! "
The price is CA $655
CA $1,434 total
includes taxes & fees
Jan 11 - Jan 12, 2025
OUTRIGGER Honua Kai Resort & Spa
Aston Kaanapali Shores
Exterior

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3394)
"We were a party of 12, with ages varying from 2-60. We shared two suites, which they helped us be right next to each other. The property was a little older and showing its age but rooms were spacious. The suites were well appointed, with well stocked kitchens for cooking and lots of storage space. Free activities were great and kept us busy, including their Christmas party, stocking votes, ukulele lessons and lei making ($). Pools were great for all ages. Being right on the beach was perfect,...
The price is CA $575
CA $721 total
includes taxes & fees
Jan 8 - Jan 9, 2025
Aston Kaanapali Shores
Royal Kahana Maui by OUTRIGGER
Condo, 2 Bedroom, Oceanfront (Unit 410, 2Bath) | Terrace/patio

Royal Kahana Maui by OUTRIGGER

3.0 star property
8.0 out of 10, Very good, (1323)
"The room was well designed with a great view of the ocean. It had cooking facility and excellent for a linger stay. The rooms have mirrors which helps with light view and makes the room bigger. The rooms also had a washer dryer and together made our stay comfortable and enjoyable"
Royal Kahana Maui by OUTRIGGER
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 $937 and CA $937 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 281 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.