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Olowalu Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Olowalu vacation rentals

Outdoor dining

1. OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC

OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC
Wailuku
9.4 out of 10, Exceptional, (175 reviews)
"Nice place and conviently located"
United States
Mike M.
$416 nightly
The price is $487
Sep 9 - Sep 10
Total with taxes and fees
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC
On the beach, sun loungers, beach towels

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

Beachfront condo in Maalaea - 2 Bedroom 2 Bath - Ground floor, AC!!!
Wailuku
9.4 out of 10, Exceptional, (66 reviews)
"Great location to harbor for whale watching and good distance between airport and beaches. "
United States
Kellie B.
$430 nightly
The price is $503
Sep 8 - Sep 9
Total with taxes and fees
Beachfront condo in Maalaea - 2 Bedroom 2 Bath - Ground floor, AC!!!
Exterior

3. Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.8 out of 10, Excellent, (37 reviews)
"Thank you for hosting us! The place was very clean and the location was fantastic, close to the beach, shops and restaurants!"
United States
Julie
$436 nightly
The price is $517
Sep 7 - Sep 8
Total with taxes and fees
Signature Residences at Maui Banyan
Property grounds

4. Bright, Beautiful, Remodeled Island Sands 505 Condo

Bright, Beautiful, Remodeled Island Sands 505 Condo
Wailuku
9.4 out of 10, Exceptional, (58 reviews)
"The property was very clean and well maintained! We enjoyed our stay. "
United States
Cindy B.
$782 nightly
The price is $819
Sep 4 - Sep 5
Total with taxes and fees
Bright, Beautiful, Remodeled Island Sands 505 Condo
On the beach, sun loungers, beach towels

5. Sugar Beach Resort Oceanview 1 bed/1 bath

Sugar Beach Resort Oceanview 1 bed/1 bath
North Kihei
9.6 out of 10, Exceptional, (120 reviews)
"Great location, great property and great condo. "
Canada
DIANNE V.
Sugar Beach Resort Oceanview 1 bed/1 bath
Outdoor dining

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
$344 nightly
The price is $403
Sep 3 - Sep 4
Total with taxes and fees
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
Exterior

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, (315 reviews)
"Kevin was a great host! Communication was prompt and he gave wonderful suggestions on places to eat, things to do.The condo was beautiful, very cozy and clean.We would definitely stay here again"
United States
Janet M.
$342 nightly
The price is $401
Sep 14 - Sep 15
Total with taxes and fees
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
On the beach

8. Romantic Beachfront Getaway

Romantic Beachfront Getaway
Maalaea Bay
9.6 out of 10, Exceptional, (43 reviews)
"Excellent location. "
United States
Thomas
$412 nightly
The price is $482
Sep 30 - Oct 1
Total with taxes and fees
Romantic Beachfront Getaway
Suite, Multiple Beds, Garden View (2 Baths) | Garden view

9. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.6 out of 10, Exceptional, (458 reviews)
"Clean room, friendly staff, great location and views!"
United States
Luis A
$543 nightly
The price is $644
Sep 3 - Sep 4
Total with taxes and fees
The Whaler Resort Kaanapali Beach
On the beach

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, (81 reviews)
"We loved our stay! Great location"
United States
Madison
$294 nightly
The price is $344
Sep 5 - Sep 6
Total with taxes and fees
Oceanside condo, full kitchen, ocean view. Fully renovated 2023
Exterior

11. 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, (1,556 reviews)
"Lovely place with full amenities and walk out patio in the lawn. Would definitely book again!"
United States
Heidi
$384 nightly
The price is $456
Sep 28 - Sep 29
Total with taxes and fees
Aston at The Whaler on Kaanapali Beach
Sun loungers, beach towels

12. 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)
"This place was in a good location in Kihei. You are within 5 mins of dozen of beaches. All the beach gear a person needs is provided(towels, chairs, snorkels, flippers, coolers and more)! Jon is super friendly and a great host!"
United States
Troy s.
$438 nightly
The price is $512
Sep 4 - Sep 5
Total with taxes and fees
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
On the beach, sun loungers, beach towels

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

Steps to the Beach, Affordable w/Free Parking
North Kihei
9.6 out of 10, Exceptional, (172 reviews)
"Clean, across the street from beach and whale center. Great location to get to other places on the island. "
Canada
wayneiversonphotosk
$374 nightly
The price is $437
Sep 13 - Sep 14
Total with taxes and fees
Steps to the Beach, Affordable w/Free Parking
Outdoor dining

14. 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, (306 reviews)
"Awesome stay, all you need around there, very quiet place, good neighbors, excellent Host and amazing commons area."
United States
pablo
$335 nightly
The price is $392
Sep 9 - Sep 10
Total with taxes and fees
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
Sun loungers

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

Ocean View 2-bedroom condo with pool and AC in wonderful Kihei
North Kihei
9.8 out of 10, Exceptional, (33 reviews)
"Property was clean and great location to do everything we wanted to do. Was very pleased for the price!!"
United States
Rachel
$402 nightly
The price is $470
Sep 3 - Sep 4
Total with taxes and fees
Ocean View 2-bedroom condo with pool and AC in wonderful Kihei
Pool

16. Beautiful Ocean View Studio!

Beautiful Ocean View Studio!
South Kihei
9.6 out of 10, Exceptional, (19 reviews)
"We loved the location and partial ocean view from the balcony. Easy walk to the beach and we had everything available that we needed for a comfortable stay. "
United States
Susan C.
$335 nightly
The price is $391
Sep 6 - Sep 7
Total with taxes and fees
Beautiful Ocean View Studio!
Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers

17. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Kannapali Beach Area
8.8 out of 10, Excellent, (2,624 reviews)
"Great place"
United States
Luis MANUEL
$294 nightly
The price is $349
Sep 5 - Sep 6
Total with taxes and fees
Aston Maui Kaanapali Villas
Smart TV, DVD player, books, streaming services

18. 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, (44 reviews)
"Had lots of great and useful amenities "
United States
Rochelle P.
$377 nightly
The price is $441
Sep 4 - Sep 5
Total with taxes and fees
Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View
Interior

19. 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 1 - Oct 2
Total with taxes and fees
Unit 22 Waena Inn - Maui Private Suite
Coffee/tea maker, fridge, microwave, oven

20. 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, (218 reviews)
"The location of the suite was perfect, close to the pool, hot tub and grills and still offered privacy."
United States
Laurie D.
$409 nightly
The price is $478
Sep 6 - Sep 7
Total with taxes and fees
Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!
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

Mana Kai Maui- Official Onsite Rental

Mana Kai Maui- Official Onsite Rental

10/10 Excellent
"The beach view was the best part of our stay. Our room was updated and clean and staff was very helpful and friendly. Amenities were good. We went during a time when construction was underway which was unfortunate but not really that big a problem."
Sandra 6-night trip
Posted 6 hours ago
Mana Kai Maui- Official Onsite Rental

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 $237 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 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.