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

1. Napili Village Hotel

Lahaina

Dawa

￥35,051 total

includes taxes & fees

Nov 8 - Nov 9

A pool with a view of the ocean and beach.

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

Wailuku

Bethany U.

￥64,979 total

includes taxes & fees

Nov 8 - Nov 9

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

3. Aston Kaanapali Shores

Lahaina

Dina

￥36,150 total

includes taxes & fees

Nov 9 - Nov 10

A beach with clear blue water, a sandy shore, and palm trees.

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

Wailuku

Kellie B.

￥82,916 total

includes taxes & fees

Nov 12 - Nov 13

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

5. The Whaler Resort Kaanapali Beach

Kannapali Beach Area

zachary

￥96,691 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

￥51,909 total

includes taxes & fees

Nov 29 - Nov 30

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

￥46,178 total

includes taxes & fees

Nov 16 - Nov 17

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

8. Romantic Beachfront Getaway

Maalaea Bay

Thomas

￥72,417 total

includes taxes & fees

Nov 22 - Nov 23

A staircase leading to a stone wall with a 'WELCOME' sign, a framed mirror, and potted plants.

9. Unit 22 Waena Inn - Maui Private Suite

Wailuku

Claire R.

￥50,979 total

includes taxes & fees

Nov 29 - Nov 30

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

10. Kuleana Club - 316

Lahaina

Howie

￥61,884 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.

￥78,254 total

includes taxes & fees

Nov 12 - Nov 13

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

￥67,032 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.

￥87,844 total

includes taxes & fees

Nov 8 - Nov 9

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

15. The Westin Nanea Ocean Villas, Ka'anapali

Lahaina

Justin

￥75,255 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.

￥145,918 total

includes taxes & fees

Nov 29 - Nov 30

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

￥62,908 total

includes taxes & fees

Nov 12 - Nov 13

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.

￥61,703 total

includes taxes & fees

Nov 16 - Nov 17

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

19. Signature Residences at Maui Banyan

South Kihei

Mai

￥81,350 total

includes taxes & fees

Nov 10 - Nov 11

An aerial view of a coastal area with a clear pathway leading to a beach, surrounded by lush greenery and rocky coastline.

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.

￥73,365 total

includes taxes & fees

Nov 16 - Nov 17

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Find vacation rentals that suit your style

Top Olowalu Hotel Reviews

A modern living room with a large gray sectional sofa, wooden beams, and a colorful mural.

Howzit Hostels

Wailuku

10/10 Excellent

Kathy

A hotel lobby with a central seating area, wooden flooring, and a mural on the wall.

Maui Seaside Hotel

Kahului

10/10 Excellent

Jazmin

A patio with wicker furniture, a table with a vase of flowers, and a view of the ocean with palm trees.

Kohea Kai Hotel Maui

North Kihei

10/10 Excellent

Anonymous traveler

A bedroom with a wooden bed, white bedding, a beach-themed picture on the wall, and a ceiling fan.

Days Inn by Wyndham Maui Oceanfront

South Kihei

10/10 Excellent

Dominador

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

Maui Coast Hotel

South Kihei

10/10 Excellent

Maui Coast Hotel was an ideal base in Kihei! It was centrally located right across the street from Kamaole I Beach, and while I wouldn't necessarily recommend staying anywhere in Kihei without a car, there were definitely places to eat and hang in walkable distance in both directions, and the hotel also offered a complementary shuttle service within a 3-mile radius. For those with cars, the plentiful free parking was a nice contrast vs the predatory parking fees at the Wailea resorts. The...

Anonymous traveler

The Whaler Resort Kaanapali Beach

Kannapali Beach Area

10/10 Excellent

The best family rental ever. For the price compared to all the other resorts you get the most bang for your buck: location, FULL KITCHEN, laundry, guest services, beach access, shopping, and the most beautiful ocean with snorkeling magic galore. We saw sharks turtles and fish by Black Rock. It was amazing. Our daughter loved her first trip to Hawaii. We will definitely be back to west Maui and highly recommend the Whaler.

Chiara

Napili Village Hotel

Lahaina

10/10 Excellent

Napili Village Hotel is a great place to stay if you want to have a nice and relaxing vacation. My room was very spacious...with a balcony, big windows, big bed plus a day bed, and kitchen. it has its own parking. it's like a 2 minute walk to Napili Bay beach...which is awesome (nice calm waters...good for swimming and snorkeling). it is also just about a 5 minute walk to Kapalua Bay beach (also just as beautiful as Napili Bay beach). there's a cafe and snorkel rental shop next door, which is...

Patricia

A covered outdoor area with a glass table and chairs, surrounded by lush greenery and a view of a mountain and buildings.

Maui What A Wonderful World B and B Hawaii

South Kihei

10/10 Excellent

Sarah

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

Samuel

A balcony with a glass table, two wicker chairs, and a potted plant with yellow flowers.

The Mauian - Boutique Beach Studios on Napili Bay

Lahaina

10/10 Excellent

Very intimate, we had the partial ocean view just steps away from the beach. Room was very clean,had everything you need stocked in the kitchen for cooking. Rooms have no air but ceiling fans and leaving windows open cool down the room and not to mention hearing the ocean waves are at night is so calming. Pool has bbqs and is awesome at night with the tiki torches lit. Thursday night they had a pool party free Maui Tais and a live singer. Everyone is so friendly and helpful. They provide beach...

Nikki

A spacious living room with a piano, a dining area with a round table, and a large mirror.

The Historic Wailuku Inn

Wailuku

10/10 Excellent

Diane

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

OUTRIGGER Kaanapali Beach Resort

Kannapali Beach Area

10/10 Excellent

John

A beach with palm trees and a clear sky.

Nona Lani Cottages

North Kihei

10/10 Excellent

Anonymous traveler

A swimming pool with lounge chairs and palm trees.

Courtyard Maui Kahului Airport

Kahului

10/10 Excellent

The hotel location was very convenient for our stay and easy access to all what you need - restaurants and groceries. Walking distance to Costco if you're its member and taking advantage of it, especially its gas price was much cheaper to the others when you have rental car like me. The hotel is very close to the airport, but I didn't feel much noise bothering my sleep there. Hotel parking is $10 per night for my stay. If you plan to do road to Hana and Haleakala national park, staying this...

Jiping

A two-story hotel with a waterfall, lush greenery, and a balcony overlooking the water.

Four Seasons Resort Lanai

Lanai City

10/10 Excellent

From the moment we landed in Lana’i we were greeted by welcoming Four Seasons Ambassadors. It was a short shuttle ride to the breathtaking resort. We were welcomed by a Ukulele player, a wet washcloth, a Hawaiin lei and a fruit beverage. Since there was a group arriving with us, Flora told us she would get us checked in. Within a few minutes we had our wristband key and she even took us to our room. The room was beautiful and the view was amazing. There was high tech lighting and...

Anonymous traveler

Maui What A Wonderful B&B Pineapple Ste

South Kihei

10/10 Excellent

Claudia

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

Laurice

Find out more about Olowalu

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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

Howzit Hostels

10/10 Excellent

Find out more about Olowalu

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?