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Olowalu Vacation Rentals

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Our top choices for Olowalu vacation 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
9.4 out of 10, Exceptional, (174 reviews)
"Nice place and conviently located"
United States
Mike M.
The price is CA $164
CA $520 total
includes taxes & fees
Aug 26 - Aug 27
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 CA $228
CA $1,110 total
includes taxes & fees
Aug 24 - Aug 25
Bright, Beautiful, Remodeled Island Sands 505 Condo

3. 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 CA $145
CA $552 total
includes taxes & fees
Sep 11 - Sep 12
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

4. 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 CA $186
CA $568 total
includes taxes & fees
Aug 23 - Aug 24
Sugar Beach Resort Oceanview 1 bed/1 bath

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, (1,555 reviews)
"Lovely place with full amenities and walk out patio in the lawn. Would definitely book again!"
United States
Heidi
The price is CA $249
CA $580 total
includes taxes & fees
Aug 30 - Aug 31
Aston at The Whaler on Kaanapali Beach

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, (306 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 CA $136
CA $540 total
includes taxes & fees
Sep 9 - Sep 10
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

7. 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.
The price is CA $138
CA $594 total
includes taxes & fees
Aug 24 - Aug 25
Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View

8. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (451 reviews)
"We love The Whaler!"
United States
Jacob
The price is CA $302
CA $862 total
includes taxes & fees
Aug 26 - Aug 27
The Whaler Resort Kaanapali Beach

9. Romantic Beachfront Getaway

Romantic Beachfront Getaway
Maalaea Bay
9.6 out of 10, Exceptional, (43 reviews)
"Excellent location. "
United States
Thomas
The price is CA $255
CA $660 total
includes taxes & fees
Aug 26 - Aug 27
Romantic Beachfront Getaway

10. 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 CA $120
CA $661 total
includes taxes & fees
Sep 4 - Sep 5
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

11. 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 CA $146
CA $553 total
includes taxes & fees
Aug 26 - Aug 27
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

12. 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 CA $211
CA $647 total
includes taxes & fees
Aug 26 - Aug 27
Top Floor Beachfront Condo with Ocean view

13. 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 CA $170
CA $584 total
includes taxes & fees
Aug 23 - Aug 24
New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.

14. Oceanside condo, full kitchen, ocean view. Fully renovated 2023

Oceanside condo, full kitchen, ocean view. Fully renovated 2023
Central Kihei
9.4 out of 10, Exceptional, (80 reviews)
"We loved our stay! Great location"
United States
Madison
The price is CA $149
CA $470 total
includes taxes & fees
Aug 27 - Aug 28
Oceanside condo, full kitchen, ocean view. Fully renovated 2023

15. 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 CA $267
CA $638 total
includes taxes & fees
Aug 31 - Sep 1
Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!

16. 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
The price is CA $209
CA $646 total
includes taxes & fees
Aug 26 - Aug 27
Ocean View 2-bedroom condo with pool and AC in wonderful Kihei

17. Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC

Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC
Lahaina
8.6 out of 10, Excellent, (108 reviews)
"Lovely room in a great location. Check in and check out were super easy, great amenities"
United States
Michaela F.
The price is CA $155
CA $1,087 total
includes taxes & fees
Sep 6 - Sep 7
Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC

18. 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
The price is CA $161
CA $598 total
includes taxes & fees
Sep 2 - Sep 3
Steps to the Beach, Affordable w/Free Parking

19. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Lahaina
8.8 out of 10, Excellent, (2,619 reviews)
"Great place"
United States
Luis MANUEL
The price is CA $320
CA $502 total
includes taxes & fees
Sep 1 - Sep 2
Aston Maui Kaanapali Villas

20. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,272 reviews)
"Great location!"
United States
Shad
The price is CA $288
CA $383 total
includes taxes & fees
Aug 25 - Aug 26
Aston Kaanapali Shores
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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.