Olowalu Vacation Rentals from CA $306: Short-Term Rentals for 2026

Q: 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.

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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

Lahaina

Shawn

CA $353 total

includes taxes & fees

Oct 25 - Oct 26

A pathway leading to a gate with a view of the ocean.

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

Lahaina

laura h.

CA $767 total

includes taxes & fees

Oct 13 - Oct 14

A tropical garden with a waterfall, lush greenery, and a gazebo.

3. Aston Kaanapali Shores

Lahaina

Roopa Rani

CA $446 total

includes taxes & fees

Oct 10 - Oct 11

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

4. Napili Village Hotel

Lahaina

ASHLEY

CA $306 total

includes taxes & fees

Nov 2 - Nov 3

A view of a beach with palm trees and a sailboat on the water.

5. The Whaler Resort Kaanapali Beach

Kannapali Beach Area

Alessio

CA $933 total

includes taxes & fees

Oct 30 - Oct 31

A swimming pool with a curved design, surrounded by palm trees and lounge chairs, with a building in the background.

6. Aston Maui Kaanapali Villas

Kannapali Beach Area

Joseph

CA $494 total

includes taxes & fees

Nov 5 - Nov 6

A beach scene with two palm trees and a view of the ocean.

7. Romantic Beachfront Getaway

Maalaea Bay

Thomas

CA $677 total

includes taxes & fees

Oct 20 - Oct 21

A beach resort with rows of palm trees, a sandy beach, and a view of the ocean.

8. Signature Residences at Maui Banyan

South Kihei

Roark

CA $737 total

includes taxes & fees

Oct 12 - Oct 13

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Top Olowalu Hotel Reviews

OUTRIGGER Kaanapali Beach Resort

10/10 Excellent

"This was a great place to stay. Right on the beach with shopping and dining options close by within walking distance. Only wish the resort had more dining options on site"

Grand Wailea Maui, A Waldorf Astoria Resort

10/10 Excellent

"From the moment I stepped into the property, I was immediately captivated by the beauty and elegance of this resort. Even the best photos I’ve taken can’t quite capture the true essence of this relaxing place! The place is exceptionally clean; the housekeeper cleaned my room even twice a day without ever interrupting me while I was in the room—I have no idea how they manage that! Everyone, from the receptionist to all the other staff members, was smiling. The 8th-floor lounge was something I didn’t expect; there was practically something to eat and drink for free (included in the room) from 6 AM to 7 PM! I could have had healthy and unhealthy meals or snacks, whatever I liked! The pools with ocean right there, swim-up bar, 24 hour store on site in addition to multiple restaurants in the resort, even a simple walk around the 4-acre area filled with flowers, trees, and a waterfall, were safe and so relaxing at night! There was a water machine for free all over the resort. That was my first perfect experience in Hawaii. I wish I could go back there soon!"

Aston Mahana at Kaanapali

8/10 Good

"Amazing view and staff are super friendly and accommodating. Seems like every room has the ocean front view. Property is clean, however our room got lots of roaches…we reported to the front desk and they immediately placed the baits but it did not solve the problem right away. Other than that everything else was perfect. Unbeatable ocean view, access to the beach is right at the building, clean beach towels, beach chairs, and well maintained BBQ area and pool / jacuzzi."

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Olowalu vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Olowalu vacation rentals we have selected for you start as low as CA $306 per night. Entering your travel dates in the search wizard 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.

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Our top choices for Olowalu vacation rentals

1. Napili Shores Maui by OUTRIGGER

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

3. Aston Kaanapali Shores

4. Napili Village Hotel

5. The Whaler Resort Kaanapali Beach

6. Aston Maui Kaanapali Villas

7. Romantic Beachfront Getaway

8. Signature Residences at Maui Banyan

9. Unit 15 Waena Inn - Maui Private Suite

10. OUTRIGGER Honua Kai Resort & Spa

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

12. 10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

13. Aston at The Whaler on Kaanapali Beach

14. Unit 23 Waena Inn - Maui Private Suite

15. Sugar Beach 102 Gorgeous Remodeled Home Beachfront Condo Home

16. Aston Maui Hill

17. Oceanfront, Hale Kai O Kihei, incredible sunsets, King bed, AC, remodeled 2023

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

19. The Westin Nanea Ocean Villas, Ka'anapali

20. 10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

Find vacation rentals that suit your style

Top Olowalu Hotel Reviews

OUTRIGGER Kaanapali Beach Resort

Royal Lahaina Resort & Bungalows

The Westin Maui Resort & Spa, Ka'anapali

Maui Coast Hotel

Fairmont Kea Lani Maui

Grand Wailea Maui, A Waldorf Astoria Resort

Maui Beach Hotel

Hilton Vacation Club Ka'anapali Beach Maui

Aston Mahana at Kaanapali

Find out more about Olowalu

Frequently asked questions

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