Olowalu Vacation Rentals

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Our top choices for Olowalu vacation rentals

OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (2,936 reviews)
"Excellent accommodations! Beautiful property! I would highly recommend this location. Julie, the concierge, was wonderful to work with!! What a gem!!!!"
United States
Deborah
The price is CA $382
CA $1,185 total
includes taxes & fees
Apr 23 - Apr 24
OUTRIGGER Honua Kai Resort & Spa

Kuau Plaza Paia Condo with Parking

Kuau Plaza Paia Condo with Parking
3.0 star property
Paia
The price is CA $422
CA $885 total
includes taxes & fees
Mar 26 - Mar 27
Kuau Plaza Paia Condo with Parking

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, (200 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 $254
CA $615 total
includes taxes & fees
Apr 3 - Apr 4
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,038 reviews)
"Beautiful location and friendly helpful staff. Nice clean rooms and resort. "
Canada
Megan Ruth
The price is CA $416
CA $534 total
includes taxes & fees
Apr 1 - Apr 2
Aston Kaanapali Shores

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (173 reviews)
"Great location "
United States
John Roger
The price is CA $328
CA $389 total
includes taxes & fees
Mar 30 - Mar 31
Napili Village Hotel

Kuleana Club - 513

Kuleana Club - 513
3.0 star property
Lahaina
10.0 out of 10, Exceptional, (1 review)
"Clean room, easy check in process, great property with great pool and little beach area to see turtles. We were on the third floor and had to carry all our suitcases up the flights of stairs but being able to see the whales off the Lanai every morning was worth it "
Australia
Andrea
The price is CA $253
CA $585 total
includes taxes & fees
Mar 26 - Mar 27
Kuleana Club - 513

Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (890 reviews)
"We really enjoyed the pool & hot tub area. The staff was very friendly & helpful & everything was great, we really enjoyed our stay at Maui Hill."
United States
Kelly
The price is CA $424
CA $503 total
includes taxes & fees
Apr 19 - Apr 20
Aston Maui Hill

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (375 reviews)
"Location is absolutely perfect…lots of space and nice kitchen amenities "
United States
Scott
The price is CA $527
CA $1,127 total
includes taxes & fees
Apr 23 - Apr 24
The Whaler Resort Kaanapali Beach

Kuau Surf 2.0 Maui North Shore Locally-Owned

Kuau Surf 2.0 Maui North Shore Locally-Owned
Paia
9.2 out of 10, Wonderful, (23 reviews)
"Clean and convenient"
United States
Ilya L
The price is CA $302
CA $515 total
includes taxes & fees
Apr 1 - Apr 2
Kuau Surf 2.0 Maui North Shore Locally-Owned

Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (654 reviews)
"beautiful view. Amazing staff! "
United States
Huajuan
The price is CA $386
CA $458 total
includes taxes & fees
Mar 27 - Mar 28
Napili Sunset on the Beach

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,776 reviews)
"Ocean view, comfortable room, nice bar on property, well located"
United States
Rosanne Marie
The price is CA $394
CA $468 total
includes taxes & fees
Apr 24 - Apr 25
Napili Shores Maui by OUTRIGGER

The Ocean View Residence

The Ocean View Residence
3.0 star property
South Kihei
10.0 out of 10, Exceptional, (1 review)
"Very nice condo for a longer-term stay. We loved being able to cook. "
United States
John
The price is CA $146
CA $883 total
includes taxes & fees
Apr 14 - Apr 15
The Ocean View Residence

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, (486 reviews)
"Wonderful place to stay. "
United States
Sharon Lynn
The price is CA $713
CA $846 total
includes taxes & fees
Apr 9 - Apr 10
The Westin Nanea Ocean Villas, Ka'anapali

BEACHFRONT condo, ocean view, steps to sea, heated pool,hot tub, AC, Sugar Beach

BEACHFRONT condo, ocean view, steps to sea, heated pool,hot tub, AC, Sugar Beach
North Kihei
10.0 out of 10, Exceptional, (136 reviews)
"Beautiful place to stay and rest. Ate all our meals on the lani in ocean front beauty. All you need for a beautiful vacation "
United States
Ruth
BEACHFRONT condo, ocean view, steps to sea, heated pool,hot tub, AC, Sugar Beach

Romantic Beachfront Getaway

Romantic Beachfront Getaway
Maalaea Bay
9.6 out of 10, Exceptional, (42 reviews)
"Excellent location. "
United States
Thomas
The price is CA $254
CA $654 total
includes taxes & fees
Mar 27 - Mar 28
Romantic Beachfront Getaway

Sugar Beach 102 Gorgeous Remodeled Home Beachfront Condo Home

Sugar Beach 102 Gorgeous Remodeled Home Beachfront Condo Home
North Kihei
9.4 out of 10, Exceptional, (44 reviews)
"The pool and hot tub are great and very easy to access. The views are stunning. And the grounds are kept incredibly clean and groomed. "
United States
Guy C.
The price is CA $295
CA $788 total
includes taxes & fees
Apr 22 - Apr 23
Sugar Beach 102 Gorgeous Remodeled Home Beachfront Condo Home

Paia 2 Bedroom 2 Bathroom

Paia 2 Bedroom 2 Bathroom
Paia
9.0 out of 10, Wonderful, (10 reviews)
"The house was perfect for the 6 of us and near a beautiful cove. "
United States
Vanessa C.
The price is CA $473
CA $981 total
includes taxes & fees
Apr 5 - Apr 6
Paia 2 Bedroom 2 Bathroom

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, (205 reviews)
"Gorgeous condo right on the beach! Zero complaints! Thank you for sharing your home."
United States
Susan C.
The price is CA $294
CA $678 total
includes taxes & fees
Apr 22 - Apr 23
Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
North Kihei
10.0 out of 10, Exceptional, (272 reviews)
"Perfectly situated on Maui island to easily visit everything and come back to condo to sleep."
Canada
Jean-Philippe R.
The price is CA $151
CA $560 total
includes taxes & fees
Apr 5 - Apr 6
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

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, (167 reviews)
"Great location on the island, nice accommodations. "
United States
Chris P.
The price is CA $163
CA $522 total
includes taxes & fees
Apr 1 - Apr 2
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC
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?

The #1 Luxury OCEAN FRONT Mansion! Sleeps 32: This vacation home rental near Olowalu is located on the beach and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 11 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

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.