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Olowalu Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Olowalu vacation rentals

A beach with clear turquoise water, sandy shore, palm trees, and a resort building in the background.

1. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,897 reviews)
"Great trip!"
United States
Jennifer
$224 nightly
The price is $266
Oct 25 - Oct 26
Total with taxes and fees
Napili Shores Maui by OUTRIGGER
A swimming pool with a curved design, surrounded by palm trees and lounge chairs, with a building in the background.

2. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Kannapali Beach Area
8.8 out of 10, Excellent, (2,645 reviews)
"Great place will stay again!"
United States
Joseph
$292 nightly
The price is $346
Nov 6 - Nov 7
Total with taxes and fees
Aston Maui Kaanapali Villas
A view of a beach with palm trees and a sailboat on the water.

3. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.6 out of 10, Exceptional, (495 reviews)
"Great place"
United States
Alessio
$561 nightly
The price is $666
Oct 12 - Oct 13
Total with taxes and fees
The Whaler Resort Kaanapali Beach
Lobby

4. Aston at The Whaler on Kaanapali Beach

Aston at The Whaler on Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.2 out of 10, Wonderful, (1,566 reviews)
"Great location, very nice condo, pool, and beach access."
United States
Stewart
$525 nightly
The price is $623
Oct 25 - Oct 26
Total with taxes and fees
Aston at The Whaler on Kaanapali Beach
A resort with a pool, palm trees, and a view of the ocean.

5. 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, (533 reviews)
"It was beautiful hotel and we love to walk to the beach."
United States
Maria
$559 nightly
The price is $664
Oct 30 - Oct 31
Total with taxes and fees
The Westin Nanea Ocean Villas, Ka'anapali
A resort pool with red umbrellas, palm trees, and a view of the ocean.

6. OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (3,065 reviews)
"Such a lovely stay. The hotel is in a great location, everyone was very kind. I would definitely stay here again!"
United States
Andrea
$794 nightly
The price is $865
Nov 11 - Nov 12
Total with taxes and fees
OUTRIGGER Honua Kai Resort & Spa
A pathway leading to a gate with a view of the ocean.

7. 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 12 - Oct 13
Total with taxes and fees
LAHAINA SHORES #105 OCEANFRONT PREMIER SUITE, 2Bath 1Bedroom GROUND FLOOR
A beach with clear blue water, palm trees, and a resort in the background.

8. Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (246 reviews)
"We loved how quiet and relaxing the property was. The employees and atmosphere were amazing."
United States
Joshua
$163 nightly
The price is $193
Nov 9 - Nov 10
Total with taxes and fees
Napili Village Hotel
A beach scene with two palm trees and a view of the ocean.

9. Romantic Beachfront Getaway

Romantic Beachfront Getaway
Maalaea Bay
9.6 out of 10, Exceptional, (43 reviews)
"Excellent location. "
United States
Thomas
$410 nightly
The price is $480
Oct 14 - Oct 15
Total with taxes and fees
Romantic Beachfront Getaway
A kitchen with wooden cabinets, stainless steel appliances, and a view of the ocean.

10. 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, (226 reviews)
"Has everything you need and you cannot beat the location. Everything works, slept great, would definitely book again"
United States
Michelle S.
$448 nightly
The price is $524
Oct 28 - Oct 29
Total with taxes and fees
Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!
A beach with clear turquoise water, a sandy shore, and some greenery.

11. Unit 15 Waena Inn - Maui Private Suite

Unit 15 Waena Inn - Maui Private Suite
Wailuku
9.4 out of 10, Exceptional, (28 reviews)
"Good place to stay"
United States
Ram
$280 nightly
The price is $313
Oct 12 - Oct 13
Total with taxes and fees
Unit 15 Waena Inn - Maui Private Suite
A resort with a swimming pool, palm trees, and ocean views.

12. Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (991 reviews)
"Way more than what we expected.. clean, well kept, extremely spacious and centrally located to shops, beaches and restaurants. Loved everything about the property"
United States
Michael
$255 nightly
The price is $302
Nov 11 - Nov 12
Total with taxes and fees
Aston Maui Hill
A balcony with a table set for two, overlooking a beach with palm trees and the ocean.

13. 🤙 Sept-Oct-Nov SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE

🤙 Sept-Oct-Nov SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE
North Kihei
10.0 out of 10, Exceptional, (144 reviews)
"We enjoyed the resort and the condo was perfect"
United States
Shelley S.
$581 nightly
The price is $680
Oct 18 - Oct 19
Total with taxes and fees
🤙 Sept-Oct-Nov SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE
A tropical garden with a waterfall, lush greenery, and a gazebo.

14. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,370 reviews)
"Great Stay"
United States
Roopa Rani
$256 nightly
The price is $304
Oct 28 - Oct 29
Total with taxes and fees
Aston Kaanapali Shores
A balcony with a view of a coastal landscape, including palm trees and a distant mountain range.

15. 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
$453 nightly
The price is $537
Oct 15 - Oct 16
Total with taxes and fees
Signature Residences at Maui Banyan
A beach view with palm trees, a clear sky, and a distant mountain.

16. Remodeled Ocean View Studio at The Whaler 518-Kaanapali Beach-Walk to Dining

Remodeled Ocean View Studio at The Whaler 518-Kaanapali Beach-Walk to Dining
Kannapali Beach Area
9.6 out of 10, Exceptional, (80 reviews)
"Nice room. You can’t go wrong at the whaler. The shower leaked a little. Overall good experience"
United States
Alaba G.
$806 nightly
The price is $913
Oct 13 - Oct 14
Total with taxes and fees
Remodeled Ocean View Studio at The Whaler 518-Kaanapali Beach-Walk to Dining
A balcony with a table set for two, featuring a bottle of wine and two glasses.

17. 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
$336 nightly
The price is $393
Oct 12 - Oct 13
Total with taxes and fees
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
A balcony with a view of palm trees and the ocean.

18. Exceptionally Remodeled Oceanfront, Sunsets, A/C, King bed Hale Kai O Kihei

Exceptionally Remodeled Oceanfront, Sunsets, A/C, King bed Hale Kai O Kihei
Central Kihei
10.0 out of 10, Exceptional, (180 reviews)
"AMAZING location!! Great beach and close to everything you need in Kihei. Would absolutely stay again!"
United States
Kendall P.
$490 nightly
The price is $573
Oct 13 - Oct 14
Total with taxes and fees
Exceptionally Remodeled Oceanfront, Sunsets, A/C, King bed Hale Kai O Kihei
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.

19. 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 pool area with lounge chairs and palm trees, overlooking the ocean at sunset.

20. Oceanfront Unit in a Gorgeous Tropical Complex with Beachfront Pool

Oceanfront Unit in a Gorgeous Tropical Complex with Beachfront Pool
Central Kihei
9.6 out of 10, Exceptional, (86 reviews)
"Great place right on the beach."
United States
Phet S.
Oceanfront Unit in a Gorgeous Tropical Complex with Beachfront Pool
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 Mahana at Kaanapali

Aston Mahana at Kaanapali

10/10 Excellent
"Staff was awesome, upper floor room was unreal, and the views were amazing. Doesnt get much more convenient for the area. The actual building is probably the closest to the water out of all of them. The beach right at the hotel is arguably the best beach we found during our entire trip for swimming and wildlife. Lots of restaurants and stores close by as well (Dukes was great). Would stay again and recommend."
Quinlan 5-night trip
Posted 5 hours ago
Aston Mahana at Kaanapali

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 $193 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.