An underwater scene with a diver and a turtle.

Olowalu Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Olowalu vacation rentals

A beach with clear blue water, palm trees, and a resort in the background.

1. Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (247 reviews)
"We loved how quiet and relaxing the property was. The employees and atmosphere were amazing."
United States
Joshua
$165 nightly
The price is $196
Nov 6 - Nov 7
Total with taxes and fees
Napili Village Hotel
A beach resort with rows of palm trees, a sandy beach, and a view of the ocean.

2. Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.8 out of 10, Excellent, (40 reviews)
"Absolutely loved our room. The kitchen was spacious and had all of the necessities. The best part was the lawn chairs, umbrella and tote bag provided in the room. Rooms large enough to relax and not feel so crowded."
United States
Mai
$437 nightly
The price is $519
Oct 19 - Oct 20
Total with taxes and fees
Signature Residences at Maui Banyan
A balcony with a table set for two, featuring a bottle of wine and two glasses.

3. 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
9.8 out of 10, Exceptional, (308 reviews)
"Awesome stay, all you need around there, very quiet place, good neighbors, excellent Host and amazing commons area."
United States
pablo
$347 nightly
The price is $406
Oct 28 - Oct 29
Total with taxes and fees
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
A view of a beach with palm trees and a sailboat on the water.

4. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.6 out of 10, Exceptional, (499 reviews)
"We loved everything and the location was perfect!!"
United States
Lenore
$561 nightly
The price is $666
Oct 18 - Oct 19
Total with taxes and fees
The Whaler Resort Kaanapali Beach
A swimming pool with a curved design, surrounded by palm trees and lounge chairs, with a building in the background.

5. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Kannapali Beach Area
8.8 out of 10, Excellent, (2,647 reviews)
"Great place will stay again!"
United States
Joseph
$272 nightly
The price is $323
Nov 16 - Nov 17
Total with taxes and fees
Aston Maui Kaanapali Villas
A table with a bottle and glasses on a red mat, surrounded by red chairs on a balcony with a view of palm trees and a tennis court.

6. 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
9.8 out of 10, Exceptional, (280 reviews)
"Absolutely perfect stay! Kevin was very kind and very communicative. I highly recommend staying here when visiting Kīhei."
United States
Sylvia
$342 nightly
The price is $399
Oct 22 - Oct 23
Total with taxes and fees
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
A resort with multiple buildings, a swimming pool, and a view of the ocean and mountains.

7. 10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
North Kihei
10.0 out of 10, Exceptional, (321 reviews)
"Clean and comfortable base for our vacation. Convenient location with easy parking."
United States
Luukia R.
$352 nightly
The price is $412
Oct 24 - Oct 25
Total with taxes and fees
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
A pathway leading to a gate with a view of the ocean.

8. LAHAINA SHORES #105 OCEANFRONT PREMIER SUITE, 2Bath 1Bedroom GROUND FLOOR

LAHAINA SHORES #105 OCEANFRONT PREMIER SUITE, 2Bath 1Bedroom GROUND FLOOR
Lahaina
10.0 out of 10, Exceptional, (179 reviews)
"Lovely stay!"
United States
laura h.
$495 nightly
The price is $578
Oct 19 - Oct 20
Total with taxes and fees
LAHAINA SHORES #105 OCEANFRONT PREMIER SUITE, 2Bath 1Bedroom GROUND FLOOR
A living room with a sofa, coffee table, and a large mirror. There is a sliding glass door leading to an outdoor area with a table and chairs.

9. Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View

Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View
North Kihei
10.0 out of 10, Exceptional, (47 reviews)
"Had lots of great and useful amenities "
United States
Rochelle P.
$371 nightly
The price is $434
Oct 22 - Oct 23
Total with taxes and fees
Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View
A beach with clear blue water, a sandy shore, and a distant mountain.

10. Oceanside condo, full kitchen, ocean view. Fully renovated 2023

Oceanside condo, full kitchen, ocean view. Fully renovated 2023
Central Kihei
9.6 out of 10, Exceptional, (89 reviews)
"Awesome spot for our honeymoon. Would recommend."
United States
Jack
$295 nightly
The price is $345
Oct 18 - Oct 19
Total with taxes and fees
Oceanside condo, full kitchen, ocean view. Fully renovated 2023
A patio with two barbecue grills, a pathway, and a view of the sea and mountains.

11. Kuleana Club - 511

Kuleana Club - 511
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (2 reviews)
"Room was very clean and well equipped. Nice pool and helpful staff in premise. "
United States
Baron
$308 nightly
The price is $365
Oct 22 - Oct 23
Total with taxes and fees
Kuleana Club - 511
A beach scene with two palm trees and a view of the ocean.

12. Romantic Beachfront Getaway

Romantic Beachfront Getaway
Maalaea Bay
9.6 out of 10, Exceptional, (43 reviews)
"Excellent location. "
United States
Thomas
$407 nightly
The price is $477
Oct 20 - Oct 21
Total with taxes and fees
Romantic Beachfront Getaway
A beachside resort with palm trees, lounge chairs, and umbrellas.

13. Top Floor Beachfront Condo with Ocean view

Top Floor Beachfront Condo with Ocean view
North Kihei
9.6 out of 10, Exceptional, (64 reviews)
"It was a beautiful place and very cozy"
United States
Stephanie T.
$386 nightly
The price is $452
Oct 18 - Oct 19
Total with taxes and fees
Top Floor Beachfront Condo with Ocean view
A beach with clear turquoise water, sandy shore, palm trees, and a resort building in the background.

14. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,903 reviews)
"We loved our stay there. We will definitely come again."
United States
Kim
$247 nightly
The price is $293
Oct 20 - Oct 21
Total with taxes and fees
Napili Shores Maui by OUTRIGGER
A staircase leading to a stone wall with a 'WELCOME' sign, a framed mirror, and potted plants.

15. Unit 22 Waena Inn - Maui Private Suite

Unit 22 Waena Inn - Maui Private Suite
Wailuku
9.8 out of 10, Exceptional, (38 reviews)
"The studio is super cute and in a convenient location, it was very clean and the check in process was really easy!"
United States
Claire R.
$279 nightly
The price is $313
Oct 21 - Oct 22
Total with taxes and fees
Unit 22 Waena Inn - Maui Private Suite
A lush garden with a patio area, including lounge chairs and a table, surrounded by dense foliage and a small building.

16. Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
North Kihei
9.8 out of 10, Exceptional, (110 reviews)
" Kīhei Casita House Stay (above the Main House): just lovely - would stay there again - reasonably priced - fully functioning everything - and easy outside access - we actually stayed in the Main House for one week and then one week in the Casita - while in the Main House the Casita was occupied and no noise issues at all. Fairly easy access to beaches and beach shopping. Excellent communication with host."
United States
Michael C.
$432 nightly
The price is $505
Oct 21 - Oct 22
Total with taxes and fees
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
A tropical garden with a waterfall, lush greenery, and a gazebo.

17. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,387 reviews)
"Great Stay"
United States
Roopa Rani
$235 nightly
The price is $279
Nov 17 - Nov 18
Total with taxes and fees
Aston Kaanapali Shores
A beach with boats, a sign about green turtles, and a clear view of the ocean.

18. Steps to the Beach, Affordable w/Free Parking

Steps to the Beach, Affordable w/Free Parking
North Kihei
9.6 out of 10, Exceptional, (175 reviews)
"Clean, across the street from beach and whale center. Great location to get to other places on the island. "
Canada
wayneiversonphotosk
$369 nightly
The price is $432
Oct 18 - Oct 19
Total with taxes and fees
Steps to the Beach, Affordable w/Free Parking
A tropical garden with a waterfall, a gazebo, and lush vegetation.

19. Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC

Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC
Lahaina
8.6 out of 10, Excellent, (111 reviews)
"Everything was great !"
United States
Michael
$673 nightly
The price is $758
Oct 18 - Oct 19
Total with taxes and fees
Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC
An aerial view of a coastal town with a beach, residential buildings, and a mountainous backdrop.

20. Experience the Magic of Maui: Your Perfect Kihei Getaway, steps from the beach!

Experience the Magic of Maui: Your Perfect Kihei Getaway, steps from the beach!
South Kihei
9.2 out of 10, Wonderful, (91 reviews)
"Location was perfect. We were there right after all of the flooding and the road was damaged but did not affect our stay at all. Our host was always responsive and made sure we were comfortable! Would surely stay again.:)"
United States
Melissa P.
$382 nightly
The price is $447
Oct 22 - Oct 23
Total with taxes and fees
Experience the Magic of Maui: Your Perfect Kihei Getaway, steps from the 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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Top Olowalu Hotel Reviews

Aston Kaanapali Shores

Aston Kaanapali Shores

8/10 Good
"The photos on site for the rooms do not give this place justice. I was definitely taken back at how much bigger the rooms were. May hire a photographer. My only other complaint was just the deposit amount could have been less. Oh I also think the daily charging fee for parking for guest wo are staying for a week was ridiculous. Other then those 2 things fantastic place."
Bennie 6-night trip
Posted 1 hour ago
Aston Kaanapali Shores

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 $196 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.

Explore a world of travel with Expedia

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.