Olowalu Vacation Rentals

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Our top choices for Olowalu vacation rentals

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,801 reviews)
"Perfect place to stay, good location"
United States
Aurelia
$257 nightly
The price is $306
Jun 13 - Jun 14
Total with taxes and fees
Napili Shores Maui by OUTRIGGER

Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (914 reviews)
"Staff was amazing and nice! The GM is a huge Kansas City Chiefs fan. The property is beautiful and is a perfect walking distance for anything Kīhei/Wailea. Great TV channels as well. There are cute roosters, lizards and birds everywhere. Will be staying here again for sure! "
Canada
Ethan
$309 nightly
The price is $367
Jun 25 - Jun 26
Total with taxes and fees
Aston Maui Hill

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (183 reviews)
"The property is beautiful and located just steps away from the beach."
United States
Patricia
$236 nightly
The price is $280
May 28 - May 29
Total with taxes and fees
Napili Village Hotel

Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,110 reviews)
"Great Beach, staff,Hot tubs, restaurant, excellent happy hour. "
United States
Kathleen
$325 nightly
The price is $386
May 31 - Jun 1
Total with taxes and fees
Aston Kaanapali Shores

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (410 reviews)
"From check-in to check-out and all days in between the staff and property were wonderful.Clean, beautiful property located in the hub of Kaanapali Beach. Always a great place to stay."
United States
Ralph
$608 nightly
The price is $722
Jun 27 - Jun 28
Total with taxes and fees
The Whaler Resort Kaanapali 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, (208 reviews)
"Great location near Paia shops and short walk to Mama's Fish House, & beach. Enjoyed our stay at Kuau Plaza. The condo was just as described and pictured. Nicely furnished & decorated. Comfy bed, everything you could need in the kitchen, nice bathroom...all looked brand new! Although right next to the road, we barely heard the traffic. We would stay here again."
United States
Kimberly
$374 nightly
The price is $439
May 28 - May 29
Total with taxes and fees
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

Paia 2 Bedroom 2 Bathroom

Paia 2 Bedroom 2 Bathroom
Paia
9.2 out of 10, Wonderful, (12 reviews)
"The house was perfect for the 6 of us and near a beautiful cove. "
United States
Vanessa C.
$520 nightly
The price is $608
Jun 2 - Jun 3
Total with taxes and fees
Paia 2 Bedroom 2 Bathroom

Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (654 reviews)
"Clean room amd friendly staff."
United States
Chris
$281 nightly
The price is $334
Jun 1 - Jun 2
Total with taxes and fees
Napili Sunset on the Beach

Kihei Ali'i Kai Condos with Free Parking

Kihei Ali'i Kai Condos with Free Parking
4.0 star property
South Kihei
9.4 out of 10, Exceptional, (36 reviews)
"Everything was set up to be an amazing experience and we would definitely stay again."
Canada
Tamara
$394 nightly
The price is $419
May 30 - May 31
Total with taxes and fees
Kihei Ali'i Kai Condos with Free Parking

Warm Winter Getaway w/ a View - BEACHFRONT PROPERTY A13 at Kihei Sands

Warm Winter Getaway w/ a View - BEACHFRONT PROPERTY A13 at Kihei Sands
North Kihei
9.8 out of 10, Exceptional, (72 reviews)
"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: It was an amazing stay and a great place! I will be back!"
United States
Lauree M.
$529 nightly
The price is $587
May 28 - May 29
Total with taxes and fees
Warm Winter Getaway w/ a View - BEACHFRONT PROPERTY A13 at Kihei Sands

OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (2,970 reviews)
"Everything about this place was great!"
United States
Jag
$925 nightly
The price is $1,007
Jun 7 - Jun 8
Total with taxes and fees
OUTRIGGER Honua Kai Resort & Spa

Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!

Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!
North Kihei
9.8 out of 10, Exceptional, (208 reviews)
"Gorgeous condo right on the beach! Zero complaints! Thank you for sharing your home."
United States
Susan C.
$405 nightly
The price is $474
May 30 - May 31
Total with taxes and fees
Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!

Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Lahaina
8.8 out of 10, Excellent, (2,570 reviews)
"Great location for beach lovers and family vacation. "
United States
meryem
$409 nightly
The price is $485
Jun 20 - Jun 21
Total with taxes and fees
Aston Maui Kaanapali Villas

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, (170 reviews)
"Great location on the island, nice accommodations. "
United States
Chris P.
$290 nightly
The price is $339
Jun 1 - Jun 2
Total with taxes and fees
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC

Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.6 out of 10, Excellent, (24 reviews)
"Thank you for hosting us! The place was very clean and the location was fantastic, close to the beach, shops and restaurants!"
United States
Julie
$448 nightly
The price is $531
May 31 - Jun 1
Total with taxes and fees
Signature Residences at Maui Banyan

The Westin Nanea Ocean Villas, Ka'anapali

The Westin Nanea Ocean Villas, Ka'anapali
4.0 star property
Lahaina
9.4 out of 10, Exceptional, (506 reviews)
"Clean room and easy access to the beach"
United States
Wonseok
$649 nightly
The price is $770
May 30 - May 31
Total with taxes and fees
The Westin Nanea Ocean Villas, Ka'anapali

Top Floor Beachfront Condo with Ocean view

Top Floor Beachfront Condo with Ocean view
North Kihei
9.8 out of 10, Exceptional, (54 reviews)
"Central location and helpful site manager "
United States
Richard W.
$445 nightly
The price is $520
Jun 1 - Jun 2
Total with taxes and fees
Top Floor Beachfront Condo with Ocean view

OCEANFRONT RESORT- WHALES+LOW WINTER RATES- Kihei Sands Beachfront Condo-B10

OCEANFRONT RESORT- WHALES+LOW WINTER RATES- Kihei Sands Beachfront Condo-B10
North Kihei
9.6 out of 10, Exceptional, (104 reviews)
"Room was great, loved the beach access! View from the balcony was nice too!"
United States
Linda W.
$649 nightly
The price is $725
Jun 2 - Jun 3
Total with taxes and fees
OCEANFRONT RESORT- WHALES+LOW WINTER RATES- Kihei Sands Beachfront Condo-B10

Ocean View 2-bedroom condo with pool and AC in wonderful Kihei

Ocean View 2-bedroom condo with pool and AC in wonderful Kihei
North Kihei
9.8 out of 10, Exceptional, (28 reviews)
"Nice place"
Canada
PC SHOP
$397 nightly
The price is $465
May 28 - May 29
Total with taxes and fees
Ocean View 2-bedroom condo with pool and AC in wonderful Kihei

2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores

2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores
South Kihei
9.8 out of 10, Exceptional, (206 reviews)
"Was very nice, enjoyed the stay"
United States
Andrew S.
$438 nightly
The price is $512
Jun 25 - Jun 26
Total with taxes and fees
2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores
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

Find out more about Olowalu

Everything you need to know about Olowalu vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Olowalu vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Olowalu vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Olowalu vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Olowalu. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Olowalu in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $306 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Olowalu rentals

At Expedia, we put the best Olowalu vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Olowalu rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Olowalu vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Olowalu. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Olowalu?

Yes, we have vacation rentals near the most popular local attractions in Olowalu, or you can go with a secluded option if you want a relaxing place to 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 vacation rentals that Olowalu has to offer?

Kaiholo Hale: This vacation home rental near 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 Whalers Village are other popular places to visit in the area.

What’s a vacation rental in Olowalu like?

A vacation rental is a private property you can stay in for several days or longer in Olowalu. Vacation rentals offer amenities such as hot tubs, fire pits, and patios to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.