A person relaxing on a beach under a tree with a view of the sea and distant mountains.

Olowalu Vacation Rentals

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.

Dates

November 2026

December 2026

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Our top choices for Olowalu vacation rentals

A building with a pool, surrounded by tropical vegetation and palm trees, overlooking a clear blue ocean.

1. Napili Village Hotel

Lahaina

Dawa

CA $314 total

includes taxes & fees

Nov 9 - Nov 10

A pool with a view of the ocean and beach.

2. 50 steps to the Ocean! Great Maui Location!

Wailuku

Bethany U.

3. Aston Kaanapali Shores

Lahaina

Dina

CA $351 total

includes taxes & fees

Nov 21 - Nov 22

A resort with a pool, palm trees, and a view of the ocean.

4. Beachfront condo in Maalaea - 2 Bedroom 2 Bath - Ground floor, AC!!!

Wailuku

Kellie B.

CA $704 total

includes taxes & fees

Nov 16 - Nov 17

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

5. The Whaler Resort Kaanapali Beach

Kannapali Beach Area

zachary

CA $867 total

includes taxes & fees

Dec 1 - Dec 2

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

Mariano

CA $430 total

includes taxes & fees

Nov 21 - Nov 22

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

7. Napili Shores Maui by OUTRIGGER

Lahaina

Steve

CA $411 total

includes taxes & fees

Nov 12 - Nov 13

A swimming pool with a view of the ocean and palm trees.

8. Romantic Beachfront Getaway

Maalaea Bay

Thomas

CA $650 total

includes taxes & fees

Nov 21 - Nov 22

A hotel room with two beds, a desk with a chair, a television, and a ceiling fan.

9. Unit 22 Waena Inn - Maui Private Suite

Wailuku

Claire R.

CA $460 total

includes taxes & fees

Nov 10 - Nov 11

A room with a dining table set for two, a blue sofa, and a view of the ocean.

10. Kuleana Club - 316

Lahaina

Howie

CA $555 total

includes taxes & fees

Nov 12 - Nov 13

A kitchen with wooden cabinets, stainless steel appliances, and a view of the ocean.

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

North Kihei

Michelle S.

CA $696 total

includes taxes & fees

Nov 22 - Nov 23

A balcony with a table set for two, featuring a bottle of wine and two glasses.

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

North Kihei

pablo

CA $598 total

includes taxes & fees

Dec 3 - Dec 4

A balcony with wicker chairs and a wooden table, overlooking a beach with palm trees and the ocean.

13. Oceanfront, Exceptionally Remodeled, Split A/C, King bed, OH the sunsets

Central Kihei

Alana C.

A modern kitchen with a granite countertop, wooden cabinets, and a large island. There is a dining area with a gray sofa and a table, and a view of a garden through large glass doors.

14. Sugar Beach 102 Gorgeous Remodeled Home Beachfront Condo Home

North Kihei

Angie W.

CA $794 total

includes taxes & fees

Nov 18 - Nov 19

15. The Westin Nanea Ocean Villas, Ka'anapali

Lahaina

Justin

CA $671 total

includes taxes & fees

Dec 2 - Dec 3

A beach view with palm trees, a clear sky, and a distant mountain.

16. The Whaler 518 – Remodeled Ocean View Studio on Kāʻanapali Beach

Kannapali Beach Area

Nate M.

CA $1,376 total

includes taxes & fees

Nov 21 - Nov 22

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.

17. 10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

North Kihei

john

CA $564 total

includes taxes & fees

Nov 9 - Nov 10

A resort with multiple buildings, a swimming pool, and a view of the ocean and mountains.

18. 10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

North Kihei

Luukia R.

CA $580 total

includes taxes & fees

Nov 12 - Nov 13

A breakfast table set on a balcony with a view of a tropical landscape.

19. Signature Residences at Maui Banyan

South Kihei

Mai

CA $797 total

includes taxes & fees

Nov 15 - Nov 16

A modern bedroom with a large bed, a wooden bench, and a tray with breakfast items.

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

North Kihei

" 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."

Michael C.

CA $654 total

includes taxes & fees

Nov 16 - Nov 17

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Find vacation rentals that suit your style

Top Olowalu Hotel Reviews

The Whaler Resort Kaanapali Beach

Kannapali Beach Area

10/10 Excellent

Akshay

A resort with a pool area, lounge chairs, and a view of the ocean.

Hyatt Regency Maui Resort & Spa

Kannapali Beach Area

10/10 Excellent

Tyson

A spacious balcony with wicker furniture, a view of the ocean, and a mountain in the distance.

Hilton Grand Vacations Club Maui Bay Villas

North Kihei

10/10 Excellent

Kristina

A swimming pool with lounge chairs and palm trees.

Courtyard Maui Kahului Airport

Kahului

10/10 Excellent

This was our first stay at the Courtyard Maui Kahului Airport. We flew into Kahului late in the evening, and were greeted by friendly staff who checked us in quickly. We only stayed one night, as we were flying out of the Kahului airport the next day to another island. For this, the location was perfect. Our room was very clean, and had everything we needed (WiFi, coffee, hair dryer, closet, plenty of pillows). The shower was very spacious, had a glass enclosure with a door that did not leak...

eternalsummer

A resort with a pool, tents, palm trees, and a view of the ocean.

Sheraton Maui Resort & Spa

Kannapali Beach Area

10/10 Excellent

Sandra

A spacious lobby with a stone-tiled floor, large wooden columns, and a reception desk.

Hyatt Vacation Club at Ka'anapali Beach, Maui

Kannapali Beach Area

10/10 Excellent

Han

A balcony with a view of the ocean and palm trees.

Maui Coast Hotel

South Kihei

10/10 Excellent

Paulino Cabalona

A resort with a large pool, palm trees, and a view of the ocean.

Hilton Vacation Club Ka'anapali Beach Maui

Kaanapali

10/10 Excellent

Rosaleen

A resort with a swimming pool, palm trees, and a view of the ocean.

OUTRIGGER Kaanapali Beach Resort

Kannapali Beach Area

10/10 Excellent

Douglas

The Westin Nanea Ocean Villas, Ka'anapali

Lahaina

10/10 Excellent

Megan

A resort with a pool, palm trees, and a night scene with fire torches.

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Kannapali Beach Area

10/10 Excellent

Carter Johannes

A resort pool area with palm trees, a pool, and a tiki torch.

Marriott's Maui Ocean Club - Lahaina & Napili Towers

Kannapali Beach Area

10/10 Excellent

Kalton

A modern bar area with a long counter, multiple stools, and a large TV screen displaying a scenic view.

Residence Inn by Marriott Maui Wailea

Wailea

10/10 Excellent

Jessica

A pool with lounge chairs and palm trees, surrounded by a building with a flat roof.

Hampton Inn & Suites Maui North Shore

Kahului

10/10 Excellent

Maryse

A staircase with a view of a garden, palm trees, and a bridge.

Fairmont Kea Lani Maui

Wailea

10/10 Excellent

Jessica

A boutique store with mannequins displaying clothing, a wooden table with various products, and a sign indicating the store is made in Hawaii.

Royal Lahaina Resort & Bungalows

Kannapali Beach Area

10/10 Excellent

Brandon

A balcony with a table set for dining, overlooking a pool and palm trees, with a view of the ocean and mountains in the distance.

Honua Kai Konea Resort by KBM

Kaanapali

10/10 Excellent

Shawn

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 $98 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.

Olowalu Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Olowalu vacation rentals

1. Napili Village Hotel

2. 50 steps to the Ocean! Great Maui Location!

3. Aston Kaanapali Shores

4. Beachfront condo in Maalaea - 2 Bedroom 2 Bath - Ground floor, AC!!!

5. The Whaler Resort Kaanapali Beach

6. Aston Maui Kaanapali Villas

7. Napili Shores Maui by OUTRIGGER

8. Romantic Beachfront Getaway

9. Unit 22 Waena Inn - Maui Private Suite

10. Kuleana Club - 316

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. Oceanfront, Exceptionally Remodeled, Split A/C, King bed, OH the sunsets

14. Sugar Beach 102 Gorgeous Remodeled Home Beachfront Condo Home

15. The Westin Nanea Ocean Villas, Ka'anapali

16. The Whaler 518 – Remodeled Ocean View Studio on Kāʻanapali Beach

17. 10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

18. 10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

19. Signature Residences at Maui Banyan

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

Find vacation rentals that suit your style

Top Olowalu Hotel Reviews

The Whaler Resort Kaanapali Beach

10/10 Excellent

Find out more about Olowalu

Olowalu vacation rentals: An excellent choice for every season

How to find incredible deals on Olowalu rentals

Frequently Asked Questions

Are there vacation rentals in Olowalu?

What are some of the best vacation rentals that Olowalu has to offer?

What’s there to see and do in Olowalu?

What’s a vacation rental in Olowalu like?