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Our top choices for Olowalu holiday rentals

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
9.6 out of 10, Exceptional, (173 reviews)
"Nice place and conviently located"
United States
Mike M.
The price is £285
includes taxes & fees
12 Aug - 13 Aug
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC

2. 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.
The price is £621
includes taxes & fees
8 Aug - 9 Aug
Bright, Beautiful, Remodeled Island Sands 505 Condo

3. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (444 reviews)
"Amazing views and location. Great employees."
United States
Ramon
The price is £472
includes taxes & fees
10 Aug - 11 Aug
The Whaler Resort Kaanapali Beach

4. Aston at The Whaler on Kaanapali Beach

Aston at The Whaler on Kaanapali Beach
4.0 star property
Lahaina
9.2 out of 10, Wonderful, (1,553 reviews)
"Lovely place with full amenities and walk out patio in the lawn. Would definitely book again!"
United States
Heidi
The price is £448
includes taxes & fees
6 Aug - 7 Aug
Aston at The Whaler on Kaanapali Beach

5. Romantic Beachfront Getaway

Romantic Beachfront Getaway
Maalaea Bay
9.6 out of 10, Exceptional, (43 reviews)
"Excellent location. "
United States
Thomas
The price is £361
includes taxes & fees
16 Aug - 17 Aug
Romantic Beachfront Getaway

6. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Lahaina
8.8 out of 10, Excellent, (2,605 reviews)
"Great location and friendly staff"
Canada
Daniel
The price is £271
includes taxes & fees
1 Sept - 2 Sept
Aston Maui Kaanapali Villas

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, (279 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 £300
includes taxes & fees
8 Aug - 9 Aug
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

8. 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, (305 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 £300
includes taxes & fees
8 Aug - 9 Aug
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

9. Top Floor Beachfront Condo with Ocean view

Top Floor Beachfront Condo with Ocean view
North Kihei
9.6 out of 10, Exceptional, (59 reviews)
"Central location and helpful site manager "
United States
Richard W.
The price is £363
includes taxes & fees
6 Aug - 7 Aug
Top Floor Beachfront Condo with Ocean view

10. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,846 reviews)
"The room was clean and the beach views and access to the beach was beyond beautiful. A really cozy place to stay."
United States
Jesus
The price is £224
includes taxes & fees
20 Aug - 21 Aug
Napili Shores Maui by OUTRIGGER

11. 🤙 June-July-August SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE

🤙 June-July-August SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE
North Kihei
10.0 out of 10, Exceptional, (142 reviews)
"This is the perfect getaway spot. Great direct view of the ocean and beach. "
United States
Mike H.
The price is £474
includes taxes & fees
6 Aug - 7 Aug
🤙 June-July-August SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE

12. 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 £237
includes taxes & fees
9 Aug - 10 Aug
Unit 22 Waena Inn - Maui Private Suite

13. 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, (314 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 £309
includes taxes & fees
12 Aug - 13 Aug
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

14. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,230 reviews)
"Great location, good value for the money."
United States
ANGELO
The price is £247
includes taxes & fees
1 Sept - 2 Sept
Aston Kaanapali Shores

15. 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.
The price is £306
includes taxes & fees
19 Aug - 20 Aug
Sugar Beach Resort Oceanview 1 bed/1 bath

16. Direct Beachfront with Spectacular Oceanviews!

Direct Beachfront with Spectacular Oceanviews!
Wailuke
9.6 out of 10, Exceptional, (59 reviews)
"The heated pool is great for kids!"
United States
RACHEAL
The price is £289
includes taxes & fees
18 Aug - 19 Aug
Direct Beachfront with Spectacular Oceanviews!

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

Oceanfront, Hale Kai O Kihei, incredible sunsets, King bed, AC, remodeled 2023
Central Kihei
10.0 out of 10, Exceptional, (120 reviews)
"Beautiful views, lovely beach, convenient parking and good amenities nearby. "
United States
Tesha T.
The price is £344
includes taxes & fees
6 Aug - 7 Aug
Oceanfront, Hale Kai O Kihei, incredible sunsets, King bed, AC, remodeled 2023

18. New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.

New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.
North Kihei
9.6 out of 10, Exceptional, (16 reviews)
"Perfect ocean views for morning coffee. Close to all the restaurants and good beaches "
United States
Michael A.
The price is £310
includes taxes & fees
9 Aug - 10 Aug
New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.

19. 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, (43 reviews)
"Had lots of great and useful amenities "
United States
Rochelle P.
The price is £345
includes taxes & fees
12 Aug - 13 Aug
Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View

20. Spectacular Summer Specials - Beachfront Condo With Amazing Oceanfront Views.

Spectacular Summer Specials - Beachfront Condo With Amazing Oceanfront Views.
North Kihei
9.6 out of 10, Exceptional, (40 reviews)
"The host responded quickly to questions. The condo was comfortable and very clean."
United States
Anonymous traveller
The price is £405
includes taxes & fees
6 Aug - 7 Aug
Spectacular Summer Specials - Beachfront Condo With Amazing Oceanfront Views.
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

Everything you need to know about Olowalu holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Olowalu holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Olowalu holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Olowalu holiday rentals we have selected for you start as low as £224 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 holiday 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 holiday.

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 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.