Photo by Claire Houston

Holiday Homes in Olowalu

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Featured Holiday Homes in Olowalu

Kaiholo Hale
Beach nearby
Kaiholo Hale
3.0 star property
9.4 out of 10, Exceptional, (184)
"Everything was so convenient and comfortable. Unit was clean and well stocked. Would recommend highly. "
Kaiholo Hale
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!
Pool
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!
10.0 out of 10, Exceptional, (2)
"After looking at dozens of home for rent, we decided on this property and do not regret the decision. It’s beautifully appointed with brand new furniture, plenty of room for a large group (we had 16) and my goodness, that beach across the street, divine! There are several areas to dine, a gorgeous pool with pool and beach toys included, and what felt like a private concierge with the manager (who lives close by). Thank you for an unforgettable vacation with my family. We will cherish the...
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!
Lana’i Oasis and Gem, The Artist's House
Interior
Lana’i Oasis and Gem, The Artist's House
10.0 out of 10, Exceptional, (174)
"My team traveled to Lana’i for a conservation event and stayed overnight at The Artist House. Jordanne was informative, friendly and communicative! The home is spacious and very clean. I was worried that it would be too warm but natural cool Lana’i breeze truly moves through the house. Check in was easy, checking out even easier. We would absolutely stay here again! Bonus points to Jordanne for having board games and puzzles available! Mahalo nui loa for a great stay!"
The price is AU$1,148
includes taxes & fees
9 Oct - 10 Oct
Lana’i Oasis and Gem, The Artist's House
Stunning Beach Front Townhouse
Property grounds
Stunning Beach Front Townhouse
10.0 out of 10, Exceptional, (82)
"This is by far the best beach front property my family and I have ever stayed at. The location was perfect. My husband joked when he was standing on the lanai that the waves were “too loud” because he couldn’t believe how close we were, haha! The beach was pleasantly sandy and you can walk for miles. While we were there we mostly had the beach to ourselves with little to almost no people. It could have been the time of year we stayed but it was very peaceful. The house was equipped with...
Stunning Beach Front Townhouse
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
Fridge, microwave, oven, stovetop
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
9.8 out of 10, Exceptional, (57)
"After staying here for a 3rd time, I decided to leave a review. This is such a fantastic home in the best location on Maui. We LOVE having the private beach in our own backyard, plenty of space to gather as a family with privacy in the bedrooms if we want it. The teens work out in the fitness center, the kids play in the pool and the adults lay out on the beach, all without leaving! Thank you so much"
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
Spacious Hawaiian home 50 steps from Sugar Beach!
Sun-loungers, beach towels
Spacious Hawaiian home 50 steps from Sugar Beach!
8.8 out of 10, Excellent, (63)
"Fabulous spot for a family with kids (3, in our case). Quiet neighborhood just a few minutes away from great food and stores. Plenty of space in the house and a cute backyard to boot. Incredibly easy to walk to the beach (crosswalk and access path). Good spot for day trips north and west. A+"
Spacious Hawaiian home 50 steps from Sugar Beach!
#1 Direct Beach Front Mansion! Pickleball, Sand Volleyball, 2 Gyms, Pool
Pool
#1 Direct Beach Front Mansion! Pickleball, Sand Volleyball, 2 Gyms, Pool
2.0 star property
10.0 out of 10, Exceptional, (2)
"We are quite familiar with luxury rentals around the world, Mexico, Italy, Hawaii and more. We can now say this is the best stay we have ever had - truly an extraordinary location on Kaanapli beach. It's brand new and in immaculate condition. We held family pickleball tournaments in the evening and then snorkled with turtles as the sun went down. It doesn't get any dreamier than this. Lastly, the home is professionally managed so you can expect 5 star hotel type service - they can pretty...
#1 Direct Beach Front Mansion! Pickleball, Sand Volleyball, 2 Gyms, Pool
Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach
Outdoor pool, a heated pool
Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach
9.8 out of 10, Exceptional, (137)
"We came to Maui for our son’s wedding. We rented this beautiful home that served as a place to relax and enjoy with immediate family. The home was very clean, easy check in and check out process, and very responsive throughout the stay! Loved everything about it and would come back again!"
Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach
Luxury Rental With Panoramic Ocean Views! High-end remodel! Large, 2bd, 3ba!
Beach nearby, sun-loungers, beach towels
Luxury Rental With Panoramic Ocean Views! High-end remodel! Large, 2bd, 3ba!
10.0 out of 10, Exceptional, (16)
"We couldn’t have been happier with our stay. The location is perfect in terms of walking to the beach, store, and other fun activities. The host was responsive and extremely helpful. And the villa is immaculate with beautiful ocean views. We will certainly stay here again next time we visit Maui. "
Luxury Rental With Panoramic Ocean Views! High-end remodel! Large, 2bd, 3ba!
Gorgeous 2 Story Townhouse on The Blue Golf Course in Wailea with Ocean View
Beach nearby, sun-loungers, beach towels
Gorgeous 2 Story Townhouse on The Blue Golf Course in Wailea with Ocean View
10.0 out of 10, Exceptional, (61)
"A return trip to Maui from our honeymoon there 21 years later, this time with our two boys. Townhome is beautiful with lots of room, watching the sunrise from Lanai looking out over #10 green of Wailea Blue golf course with view of ocean and Molokini not too far away…stunning. Great location with countless beaches and restaurants all close by. We’d go back every year if we could!"
Gorgeous 2 Story Townhouse on The Blue Golf Course in Wailea with Ocean View
Kihei Ocean Front Hale - Private Home w/ Dramatic Ocean Views on famed Halama St
Beach nearby
Kihei Ocean Front Hale - Private Home w/ Dramatic Ocean Views on famed Halama St
2.0 star property
9.8 out of 10, Exceptional, (62)
"Home was all that was advertised. We had a very pleasant vacation. We were comfortable without feeling like we were going to break something, yet in a beautiful home. Amazed at how thoughtful the supplies were, eg: beach towels, beach chairs, linens, etc. Would rent again."
Kihei Ocean Front Hale - Private Home w/ Dramatic Ocean Views on famed Halama St
The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach!
Pool
The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach!
10.0 out of 10, Exceptional, (81)
"Beautiful home as picture…even better in person. We were a family of 14, ages 2-91 and the home was well suited for alll ages. All amenities included and host was responsive and welcoming. We loved our stay. "
The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach!
Private & Fabulous views! Exclusive pool, spa and 1 acre yard
Exterior
Private & Fabulous views! Exclusive pool, spa and 1 acre yard
10.0 out of 10, Exceptional, (121)
"Beautiful, clean,quiet. Has everything you need "
Private & Fabulous views! Exclusive pool, spa and 1 acre yard
The Best of the Best JUST GOT BETTER with 3rd Remodel
Dining
The Best of the Best JUST GOT BETTER with 3rd Remodel
9.8 out of 10, Exceptional, (210)
"We had an amazing stay at this condo. Brian was very easy to work with during the entire process, and provided clear and thorough information regarding everything we needed to know as we prepared for our trip. The condo is in a beautifully maintained resort with friendly staff, great activities and an amazing location. The beach is a very short walk, as are several restaurants and a grocery store. The condo itself was perfect for our large group ... plenty of space and well stocked with...
The Best of the Best JUST GOT BETTER with 3rd Remodel
Summit Residence at KAANAPALI VISTA~4500 sf~5B/5.5B Pool/Ocean View~
A heated pool
Summit Residence at KAANAPALI VISTA~4500 sf~5B/5.5B Pool/Ocean View~
10.0 out of 10, Exceptional, (119)
"We loved our stay! The house was everything we wanted and more. The Maui staff were very helpful and left nothing to chance. The location was super convenient. We would love to come back!"
Summit Residence at KAANAPALI VISTA~4500 sf~5B/5.5B Pool/Ocean View~
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
Exterior
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
10.0 out of 10, Exceptional, (207)
"My family and I had al wonderful time. The home was large enough for all of us to enjoy together and yet have our own little space. The location is so beautiful and quiet. I was able to get some good rest. The kitchen was clean and large enough to prepare meals for my family. The house was and property is clean and I am ready to book this home for another staycation 🌺 Mahalo nui, Ohana Kanuha 🌺"
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
Maui Vacation Home w/Dazzling Oceanfront Views Honu Hale (Turtle House)
On the beach
Maui Vacation Home w/Dazzling Oceanfront Views Honu Hale (Turtle House)
9.6 out of 10, Exceptional, (19)
"Large house that easily accommodated our family. Outside deck has fabulous ocean views. Whales and sea turtles were abundant and great to watch. The house was fairly well appointed, but a bit dated. Upstairs shower leaked into the master bathroom. Wine coolers did not cool. Communication with the property team was excellent and they checked in with us throughout our stay. Overall an excellent property."
Maui Vacation Home w/Dazzling Oceanfront Views Honu Hale (Turtle House)
Spectacular Ocean View. Close to Beaches & Shopping Plaza. Large Pool & Spa.
Beach
Spectacular Ocean View. Close to Beaches & Shopping Plaza. Large Pool & Spa.
9.4 out of 10, Exceptional, (77)
"We had a great time. Everyone enjoyed the house, the pool, the hot tub and the games. It was great that all the rooms had their own AC and it was very comfortable for our family."
Spectacular Ocean View. Close to Beaches & Shopping Plaza. Large Pool & Spa.
Beautiful house in the Upscale Maui Meadows neighborhood
Beach/ocean view
Beautiful house in the Upscale Maui Meadows neighborhood
10.0 out of 10, Exceptional, (4)
"What an exceptional way to celebrate our 50th wedding anniversary! My husband & I took our family with us to Maui to stay in this outstanding home. Thank you for sharing your home with us! The property manager Diane was awesome! She was such a beautiful person and our family experienced a lifetime of memories in which she was a vital part! Thank you for all of the great memories, the wine was a lovely touch, the grandchildren and adults alike enjoyed the coconut water, the mango’s and the...
Beautiful house in the Upscale Maui Meadows neighborhood
Sugar Beach Resort condo with ocean view, AC - surf, bike & golf
Pool
Sugar Beach Resort condo with ocean view, AC - surf, bike & golf
9.0 out of 10, Wonderful, (42)
"We thoroughly enjoyed our stay here! The furniture is outdated. It is a cozy little porch and the beach access is amazing! So convenient to nearby restaurants and shops."
Sugar Beach Resort condo with ocean view, AC - surf, bike & golf
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See all available properties in Olowalu
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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Other property types in Olowalu

Aston Kaanapali Shores
Exterior
Aston Kaanapali Shores
3.5 star property
8.6 out of 10, Excellent, (3272)
"Very nice clean and quiet area. The staff were friendly and the overall room was clean and everything was functional. Both pools were clean and the surrounding as well. The location is close to local stores nearby. Our room was outdated but saw some newer updates options. The massage location was convenient and great service that was a quick walk away. "
The price is AU$529
includes taxes & fees
23 Oct - 24 Oct
Aston Kaanapali Shores
Aston Maui Kaanapali Villas
Exterior
Aston Maui Kaanapali Villas
3.0 star property
8.6 out of 10, Excellent, (2269)
"Very nice stay that is only a minute walk from the beach. "
The price is AU$606
includes taxes & fees
26 Oct - 27 Oct
Aston Maui Kaanapali Villas
OUTRIGGER Honua Kai Resort & Spa
4 outdoor pools, open 8:00 AM to 10:00 PM, pool cabanas (surcharge)
OUTRIGGER Honua Kai Resort & Spa
4.0 star property
8.8 out of 10, Excellent, (2609)
"Overall I thought the property was great! Easy walk to the beach and other hotel restaurants. We enjoyed several meals at Dukes restaurant on site. There are some areas where the property needs updates such as the pool/hot tub tiles, showers, and chairs on balcony. "
The price is AU$1,343
includes taxes & fees
2 Oct - 3 Oct
OUTRIGGER Honua Kai Resort & Spa
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.