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Olowalu Holiday Rentals

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Our top choices for Olowalu holiday rentals

1. 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, (178 reviews)
"Lovely stay!"
United States
laura h.
The price is NZ$919
includes taxes & fees
5 Oct - 6 Oct
LAHAINA SHORES #105 OCEANFRONT PREMIER SUITE, 2Bath 1Bedroom GROUND FLOOR

2. Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.8 out of 10, Excellent, (39 reviews)
"It was as good as a motel 6 bed was comfortable and my beach front condo as it was described was a room facing a mountain that you couldn’t see passed the forest of plants in front of back patio and the ac unit was very old and loud but served its purpose"
United States
Roark
The price is NZ$913
includes taxes & fees
29 Sept - 30 Sept
Signature Residences at Maui Banyan

3. Romantic Beachfront Getaway

Romantic Beachfront Getaway
Maalaea Bay
9.6 out of 10, Exceptional, (43 reviews)
"Excellent location. "
United States
Thomas
The price is NZ$847
includes taxes & fees
30 Sept - 1 Oct
Romantic Beachfront Getaway

4. 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
The price is NZ$685
includes taxes & fees
29 Sept - 30 Sept
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

5. 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, (47 reviews)
"Had lots of great and useful amenities "
United States
Rochelle P.
The price is NZ$734
includes taxes & fees
1 Oct - 2 Oct
Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View

6. 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, (317 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.
The price is NZ$709
includes taxes & fees
29 Sept - 30 Sept
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

7. 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
The price is NZ$691
includes taxes & fees
29 Sept - 30 Sept
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

8. 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, (222 reviews)
"Has everything you need and you cannot beat the location. Everything works, slept great, would definitely book again"
United States
Michelle S.
The price is NZ$922
includes taxes & fees
28 Oct - 29 Oct
Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!

9. 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, (88 reviews)
"We loved our stay! Great location"
United States
Madison
The price is NZ$593
includes taxes & fees
2 Oct - 3 Oct
Oceanside condo, full kitchen, ocean view. Fully renovated 2023

10. Top Floor Beachfront Condo with Ocean view

Top Floor Beachfront Condo with Ocean view
North Kihei
9.6 out of 10, Exceptional, (61 reviews)
"It was a beautiful place and very cozy"
United States
Stephanie T.
The price is NZ$804
includes taxes & fees
1 Oct - 2 Oct
Top Floor Beachfront Condo with Ocean view

11. Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (236 reviews)
"thank you for the best stay! perfect location, stunning beach with walking distance to beach, cafe, and rentals. room had everything we needed, recommend upgrading to ocean view it was a treat!"
United States
ASHLEY
The price is NZ$382
includes taxes & fees
30 Sept - 1 Oct
Napili Village Hotel

12. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.6 out of 10, Exceptional, (478 reviews)
"Great place"
United States
Alessio
The price is NZ$1,160
includes taxes & fees
5 Oct - 6 Oct
The Whaler Resort Kaanapali Beach

13. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Kannapali Beach Area
8.8 out of 10, Excellent, (2,638 reviews)
"The property was a fantastic place to stay. The beach that is in front of the property is excellent for swimming and snorkeling."
United States
Marie
The price is NZ$635
includes taxes & fees
11 Oct - 12 Oct
Aston Maui Kaanapali Villas

14. 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.
The price is NZ$541
includes taxes & fees
29 Sept - 30 Sept
Unit 22 Waena Inn - Maui Private Suite

15. Unit 23 Waena Inn - Maui Private Suite

Unit 23 Waena Inn - Maui Private Suite
Wailuku
10.0 out of 10, Exceptional, (12 reviews)
"Fairly central location. Helpful and due to the length of our stay, offered for us to use washer/dryer, snorkels, beach towels. "
United States
Suzan F.
The price is NZ$571
includes taxes & fees
8 Oct - 9 Oct
Unit 23 Waena Inn - Maui Private Suite

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

Steps to the Beach, Affordable w/Free Parking
North Kihei
9.6 out of 10, Exceptional, (174 reviews)
"Clean, across the street from beach and whale center. Great location to get to other places on the island. "
Canada
wayneiversonphotosk
The price is NZ$770
includes taxes & fees
29 Sept - 30 Sept
Steps to the Beach, Affordable w/Free Parking

17. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,336 reviews)
"Great Stay"
United States
Roopa Rani
The price is NZ$520
includes taxes & fees
29 Sept - 30 Sept
Aston Kaanapali Shores

18. 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.
The price is NZ$882
includes taxes & fees
30 Sept - 1 Oct
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

19. 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.
The price is NZ$968
includes taxes & fees
9 Oct - 10 Oct
Oceanfront Unit in a Gorgeous Tropical Complex with Beachfront Pool

20. Sugar Beach 102 Gorgeous Remodeled Home Beachfront Condo Home

Sugar Beach 102 Gorgeous Remodeled Home Beachfront Condo Home
North Kihei
9.4 out of 10, Exceptional, (47 reviews)
"The pool and hot tub are great and very easy to access. The views are stunning. And the grounds are kept incredibly clean and groomed. "
United States
Guy C.
Sugar Beach 102 Gorgeous Remodeled Home Beachfront Condo Home
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

Find out more about Olowalu

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Olowalu holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Olowalu. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Olowalu. Seeing all the best attractions is bound to make you fall in love with Olowalu. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Olowalu short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Olowalu?

Yes, there are holiday rentals close to the most popular sights in Olowalu, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Olowalu has to offer?

Kaiholo Hale: This holiday home rental outside of 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 holiday rental in Olowalu like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Olowalu. Holiday rentals feature extras such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for a small group gathering.