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Olowalu Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

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, (174 reviews)
"Nice place and conviently located"
United States
Mike M.
The price is ￥18,915
￥60,080 total
includes taxes & fees
Aug 24 - Aug 25
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC
Property grounds

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 ￥26,322
￥130,201 total
includes taxes & fees
Sep 5 - Sep 6
Bright, Beautiful, Remodeled Island Sands 505 Condo
Exterior

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 ￥16,761
￥63,848 total
includes taxes & fees
Sep 11 - Sep 12
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
On the beach, sun loungers, beach towels

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 ￥21,458
￥65,983 total
includes taxes & fees
Aug 23 - Aug 24
Sugar Beach Resort Oceanview 1 bed/1 bath
Penthouse, 2 Bedrooms, Oceanfront | Premium bedding, in-room safe, desk, blackout drapes

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 ￥28,738
￥66,947 total
includes taxes & fees
Aug 30 - Aug 31
Aston at The Whaler on Kaanapali Beach
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, (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 ￥15,704
￥62,429 total
includes taxes & fees
Sep 9 - Sep 10
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
Smart TV, DVD player, books, streaming services

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 ￥15,895
￥68,814 total
includes taxes & fees
Aug 24 - Aug 25
Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View
Suite, Multiple Beds, Garden View (2 Baths) | Garden 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 ￥36,145
￥100,984 total
includes taxes & fees
Aug 23 - Aug 24
The Whaler Resort Kaanapali Beach
On the 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 ￥29,406
￥76,584 total
includes taxes & fees
Aug 26 - Aug 27
Romantic Beachfront Getaway
Sun loungers, beach towels

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 ￥13,876
￥77,017 total
includes taxes & fees
Aug 23 - Aug 24
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
Outdoor dining

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 ￥16,912
￥64,028 total
includes taxes & fees
Aug 26 - Aug 27
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
Property grounds

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 ￥24,319
￥74,598 total
includes taxes & fees
Aug 24 - Aug 25
Top Floor Beachfront Condo with Ocean view
On the beach, sun loungers, beach towels

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 ￥19,630
￥67,757 total
includes taxes & fees
Aug 23 - Aug 24
New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.
On the beach

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 ￥17,167
￥54,676 total
includes taxes & fees
Aug 27 - Aug 28
Oceanside condo, full kitchen, ocean view. Fully renovated 2023
Coffee/tea maker, fridge, microwave, oven

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 ￥34,047
￥78,486 total
includes taxes & fees
Aug 29 - Aug 30
Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!
Sun loungers

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 ￥24,176
￥74,426 total
includes taxes & fees
Aug 27 - Aug 28
Ocean View 2-bedroom condo with pool and AC in wonderful Kihei
Property grounds

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 ￥17,961
￥125,540 total
includes taxes & fees
Sep 5 - Sep 6
Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC
On the beach, sun loungers, beach towels

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 ￥18,597
￥69,192 total
includes taxes & fees
Sep 1 - Sep 2
Steps to the Beach, Affordable w/Free Parking
Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers

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 ￥36,966
￥58,034 total
includes taxes & fees
Sep 1 - Sep 2
Aston Maui Kaanapali Villas
Garden

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 ￥33,268
￥44,212 total
includes taxes & fees
Aug 24 - Aug 25
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

Maui Seaside Hotel

Maui Seaside Hotel

10/10 Excellent
"The location"
Enrique 7-night trip
Posted 8 hours ago
Maui Seaside Hotel

Find out more about Olowalu

Search for holiday rentals in Olowalu on Expedia! You can easily find your home rentals, villas, holiday apartments in Olowalu using one of the methods below:

  • View our selection of featured holiday rentals in Olowalu
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Look no further and take a look at our great range of rental properties in Olowalu!

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.