Olowalu Vacation Rentals

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Our top choices for Olowalu vacation rentals

Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (906 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
The price is CA $382
CA $453 total
includes taxes & fees
May 13 - May 14
Aston Maui Hill

Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,091 reviews)
"Nice and safe place to stay"
United States
Kristen
The price is CA $360
CA $468 total
includes taxes & fees
May 11 - May 12
Aston Kaanapali Shores

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,793 reviews)
"Super clean room with fantastic view of the sea. Short walk to Napili beach. Great breakfast at the Gazebo restaurant "
United States
Mark
The price is CA $304
CA $361 total
includes taxes & fees
May 14 - May 15
Napili Shores Maui by OUTRIGGER

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (182 reviews)
"The property is beautiful and located just steps away from the beach."
United States
Patricia
The price is CA $348
CA $413 total
includes taxes & fees
May 11 - May 12
Napili Village Hotel

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (397 reviews)
"Great service, clean rooms, friendly staff, and perfectly located. We had a great time."
United States
Forest Daniel
The price is CA $418
CA $996 total
includes taxes & fees
May 13 - May 14
The Whaler Resort Kaanapali Beach

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
The price is CA $385
CA $457 total
includes taxes & fees
May 11 - May 12
Napili Sunset on the Beach

Kuau Surf 2.0 Maui North Shore Locally-Owned

Kuau Surf 2.0 Maui North Shore Locally-Owned
Paia
8.8 out of 10, Excellent, (27 reviews)
"Clean and convenient"
United States
Ilya L
The price is CA $274
CA $488 total
includes taxes & fees
May 13 - May 14
Kuau Surf 2.0 Maui North Shore Locally-Owned

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, (206 reviews)
"Recently renovated and spotless! This condo had everything we needed and was comfortable and conveniently located. Highly recommend!"
United States
Allison H.
The price is CA $253
CA $613 total
includes taxes & fees
May 13 - May 14
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, (11 reviews)
"The house was perfect for the 6 of us and near a beautiful cove. "
United States
Vanessa C.
The price is CA $412
CA $897 total
includes taxes & fees
May 13 - May 14
Paia 2 Bedroom 2 Bathroom

Bright, Beautiful, Remodeled Island Sands 505 Condo

Bright, Beautiful, Remodeled Island Sands 505 Condo
Wailuku
9.4 out of 10, Exceptional, (57 reviews)
"The property was very clean and well maintained! We enjoyed our stay. "
United States
Cindy B.
The price is CA $282
CA $1,199 total
includes taxes & fees
Jun 7 - Jun 8
Bright, Beautiful, Remodeled Island Sands 505 Condo

Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Lahaina
8.8 out of 10, Excellent, (2,564 reviews)
"Great location for beach lovers and family vacation. "
United States
meryem
The price is CA $410
CA $608 total
includes taxes & fees
Jun 8 - Jun 9
Aston Maui Kaanapali Villas

SUMMER SPECIAL!!! OWNER HOST DIRECT OCEAN FRONT Longest Sandy Beach on Maui

SUMMER SPECIAL!!! OWNER HOST DIRECT OCEAN FRONT Longest Sandy Beach on Maui
North Kihei
10.0 out of 10, Exceptional, (147 reviews)
"Our host was helpful and answered our questions in a timely manner. The amenities were great and the beach was not crowded."
United States
Thomas F.
The price is CA $342
CA $814 total
includes taxes & fees
May 11 - May 12
SUMMER SPECIAL!!! OWNER HOST DIRECT OCEAN FRONT Longest Sandy Beach on Maui

OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (2,961 reviews)
"Everything about this place was great!"
United States
Jag
The price is CA $557
CA $1,390 total
includes taxes & fees
May 11 - May 12
OUTRIGGER Honua Kai Resort & Spa

Direct Beachfront Newly Remodeled!

Direct Beachfront Newly Remodeled!
North Kihei
9.2 out of 10, Wonderful, (29 reviews)
"Very nice right on the beach "
United States
MATILDA
The price is CA $505
CA $634 total
includes taxes & fees
May 29 - May 30
Direct Beachfront Newly Remodeled!

Honua Kai Konea Resort by KBM

Honua Kai Konea Resort by KBM
4.5 star property
Kaanapali
9.6 out of 10, Exceptional, (88 reviews)
"Amazing stayThis was our honeymoon. I would definitely come back again"
United States
Annette
The price is CA $1,885
CA $2,803 total
includes taxes & fees
May 15 - May 16
Honua Kai Konea Resort by KBM

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, (497 reviews)
"Clean room and easy access to the beach"
United States
Wonseok
The price is CA $710
CA $843 total
includes taxes & fees
Jun 5 - Jun 6
The Westin Nanea Ocean Villas, Ka'anapali

Experience paradise at Kahana's beachfront 3-bedroom condo near Kaanapali Beach

Experience paradise at Kahana's beachfront 3-bedroom condo near Kaanapali Beach
Lahaina
10.0 out of 10, Exceptional, (167 reviews)
"The amenities were outstanding!"
United States
Karol S.
The price is CA $923
CA $1,952 total
includes taxes & fees
May 17 - May 18
Experience paradise at Kahana's beachfront 3-bedroom condo near Kaanapali Beach

Kihei Ali'i Kai Condos with Free Parking

Kihei Ali'i Kai Condos with Free Parking
4.0 star property
South Kihei
9.2 out of 10, Wonderful, (32 reviews)
"Everything was set up to be an amazing experience and we would definitely stay again."
Canada
Tamara
The price is CA $190
CA $583 total
includes taxes & fees
May 11 - May 12
Kihei Ali'i Kai Condos with Free Parking

Direct Beachfront with Spectacular Oceanviews!

Direct Beachfront with Spectacular Oceanviews!
Wailuke
9.8 out of 10, Exceptional, (53 reviews)
"Awesome little spot. Exactly what me and my wife were looking for. Highly recommend it! Had everything we needed and was close to all the spots we wanted to check out."
United States
Garrett F.
The price is CA $353
CA $436 total
includes taxes & fees
May 11 - May 12
Direct Beachfront with Spectacular Oceanviews!

Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
9.0 out of 10, Wonderful, (22 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
The price is CA $74
CA $726 total
includes taxes & fees
Jun 5 - Jun 6
Signature Residences at Maui Banyan
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Olowalu. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.