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Olowalu Holiday Rentals

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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 NZ$680
includes taxes & fees
22 Aug - 23 Aug
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC

2. 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$811
includes taxes & fees
26 Aug - 27 Aug
Romantic Beachfront Getaway

3. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (448 reviews)
"Amazing views and location. Great employees."
United States
Ramon
The price is NZ$1,084
includes taxes & fees
17 Aug - 18 Aug
The Whaler Resort Kaanapali Beach

4. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,850 reviews)
"Wonderful Beach and right next door to kapalua!"
United States
joe
The price is NZ$612
includes taxes & fees
2 Sept - 3 Sept
Napili Shores Maui by OUTRIGGER

5. 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, (1,554 reviews)
"Lovely place with full amenities and walk out patio in the lawn. Would definitely book again!"
United States
Heidi
The price is NZ$1,019
includes taxes & fees
18 Aug - 19 Aug
Aston at The Whaler on Kaanapali Beach

6. 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 NZ$1,357
includes taxes & fees
18 Aug - 19 Aug
Bright, Beautiful, Remodeled Island Sands 505 Condo

7. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Lahaina
8.8 out of 10, Excellent, (2,613 reviews)
"Great location and friendly staff"
Canada
Daniel
The price is NZ$623
includes taxes & fees
1 Sept - 2 Sept
Aston Maui Kaanapali Villas

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, (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 NZ$662
includes taxes & fees
15 Aug - 16 Aug
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

9. 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 NZ$582
includes taxes & fees
17 Aug - 18 Aug
Direct Beachfront with Spectacular Oceanviews!

10. 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 NZ$699
includes taxes & fees
19 Aug - 20 Aug
Sugar Beach Resort Oceanview 1 bed/1 bath

11. A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
Kuau
9.4 out of 10, Exceptional, (215 reviews)
"We had a great time! Everything was perfect. "
United States
Samantha S.
The price is NZ$757
includes taxes & fees
18 Aug - 19 Aug
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

12. 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, (216 reviews)
"The location of the suite was perfect, close to the pool, hot tub and grills and still offered privacy."
United States
Laurie D.
The price is NZ$792
includes taxes & fees
20 Aug - 21 Aug
Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!

13. 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$547
includes taxes & fees
25 Aug - 26 Aug
Unit 22 Waena Inn - Maui Private Suite

14. Top Floor Beachfront Condo with Ocean view

Top Floor Beachfront Condo with Ocean view
North Kihei
9.6 out of 10, Exceptional, (59 reviews)
"This is a great place to stay. Kristal was really helpful, both with questions about the condo and with suggestions of things to do. Great mid island location; we went to both sides of the island from here. Condo was stocked with essential items, which was much appreciated. Beautiful view and easy beach access. Highly recommend!!"
United States
Lisa J.
The price is NZ$797
includes taxes & fees
24 Aug - 25 Aug
Top Floor Beachfront Condo with Ocean view

15. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,254 reviews)
"Great location, clean rooms and great service!"
Mexico
Monique Nicole
The price is NZ$495
includes taxes & fees
2 Sept - 3 Sept
Aston Kaanapali Shores

16. 🤙 Sept-Oct-Nov SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE

🤙 Sept-Oct-Nov SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE
North Kihei
10.0 out of 10, Exceptional, (142 reviews)
"We enjoyed the resort and the condo was perfect"
United States
Shelley S.
The price is NZ$1,092
includes taxes & fees
20 Aug - 21 Aug
🤙 Sept-Oct-Nov SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE

17. 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.
The price is NZ$658
includes taxes & fees
15 Aug - 16 Aug
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

18. Panoramic Maui Sunset Ocean Views

Panoramic Maui Sunset Ocean Views
Central Kihei
9.2 out of 10, Wonderful, (57 reviews)
"The beach view was excellent! Loved this condo and would definitely stay there again. The room configuration was perfect for us."
United States
Nerida H.
The price is NZ$1,361
includes taxes & fees
22 Aug - 23 Aug
Panoramic Maui Sunset Ocean Views

19. Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (957 reviews)
"Everything was perfect and clean"
United States
Kathy
The price is NZ$614
includes taxes & fees
20 Aug - 21 Aug
Aston Maui Hill

20. 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 NZ$664
includes taxes & fees
9 Sept - 10 Sept
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
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.