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Compare Vacation Homes in Olowalu with updated reviews, rates, and availability.

Outdoor pool
The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach!
10.0 out of 10, Exceptional, (72)
"We decided to leave a review after our 4th annual stay at this beautiful home. We are constantly blown away by the quality, the rare location right off Napili Bay and the 5 star management. This home can host large groups of every age also! What a treat to return each year and see the property get better and better. If you want the trip of your dreams, be sure to look here first. The furniture looks brand new every time we come"
The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach!
Exterior
Very private. Fabulous views! Private pool, spa and yard on 1 acre!
10.0 out of 10, Exceptional, (114)
"This property exceeded our expectations and was amazing. 10 out of 10. Everything was as it should be and there was no reason to contact the Owner Mark or property manager during our stay. The views from the mid deck are amazing and the perfect place to hang out. We didn't want to leave! Mark, the Owner, is excellent and answered all of our questions prior to our stay!"
Very private. Fabulous views! Private pool, spa and yard on 1 acre!
Interior
Lana’i Oasis and Gem, The Artist's House
10.0 out of 10, Exceptional, (169)
"We’ve stayed at this property multiple times. Always in great condition and the privacy of the deck is wonderful."
The price is $415
$785 total
includes taxes & fees
May 14 - May 15
Lana’i Oasis and Gem, The Artist's House
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Beach nearby, sun loungers, beach towels
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
10.0 out of 10, Exceptional, (36)
"We enjoyed our stay at Amber and Jeremy's place. They were able to accommodate an early check in and we were very comfortable for our 1 week stay and enjoyed the pool and beach nearby. We hope to return soon."
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
Pool
Panoramic Views - Fourth Row Ho'olei - One of a Kind
10.0 out of 10, Exceptional, (18)
"Beautiful property, great location, stunning views, very well appointed. Would definitely book this property again."
Panoramic Views - Fourth Row Ho'olei - One of a Kind
Sun loungers, beach towels
Stunning Two Story Townhouse located in Ekahi Village!
10.0 out of 10, Exceptional, (26)
"Location and accommodation was excellent, thank you!"
Stunning Two Story Townhouse located in Ekahi Village!
Beach nearby, beach towels
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
10.0 out of 10, Exceptional, (73)
"Dan & Kelly thought of everything with their home. It is beautiful, warm and welcoming. Had great family card games every night outside. Great location to any and everything. Would stay again for sure. Thank you!"
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
Pool | Outdoor pool
Celebrity Estate, Across the Street From Beach! Brand New! 6 Bedroom W/Pool
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 Estate, Across the Street From Beach! Brand New! 6 Bedroom W/Pool
Sun loungers
Maui Breeze Retreat at Ho'olei...available July 13-Aug 2 & Aug.11-23. Book now!
10.0 out of 10, Exceptional, (117)
"My family of 5 stayed at Steve’s place for 9 days. Before booking I read all of the reviews about this property and thought how can every single one be so perfectly positive. Well now I know why - - the house is just fantastic. Great location, great pool, great views, great host. You will not be disappointed in any way. I can’t even think of a single negative thing about the whole experience. Once you open up the sliding doors the entire house feels like it’s outdoors! We had a slight mishap...
Maui Breeze Retreat at Ho'olei...available July 13-Aug 2 & Aug.11-23. Book now!
A heated pool
Maui Designer Beach Villa, Wailea, Ho'olei 39-2
10.0 out of 10, Exceptional, (16)
"This villa at Ho'olei is my new favorite place to be. Relaxing atmosphere, designer furniture and fixtures, modern and elegant, and very convenient to the rest of Wailea. We enjoyed a fun girls weekend here to celebrate some milestones and couldn't have asked for a better host or accommodations. The designer look of this place speaks volume about how well maintained this unit is and how immaculate it is kept. Everything you could possibly need to host a getaway with friends was found easily in...
Maui Designer Beach Villa, Wailea, Ho'olei 39-2
Aerial view
Maaleaa Surf C5 Oceanfront townhouse on miles of Sandy Beach
10.0 out of 10, Exceptional, (1)
"Everything about this property was perfect. Beautifully updated and very clean. Will look forward to booking again in the future"
The price is $310
$804 total
includes taxes & fees
May 19 - May 20
Maaleaa Surf C5 Oceanfront townhouse on miles of Sandy Beach
Outdoor dining
The Ilima Suite at the Historic Wailuku Inn Maui
10.0 out of 10, Exceptional, (2)
The price is $234
$310 total
includes taxes & fees
May 14 - May 15
The Ilima Suite at the Historic Wailuku Inn Maui
Fridge, microwave, oven, stovetop
NEW Construction! Just Steps from Maui's Best Beach!
10.0 out of 10, Exceptional, (59)
"This house was the perfect spot for our Maui Family Vacation. There were 11 of us (6 adults and 5 kids ages 6 years to 12 years) celebrating our 50th wedding anniversary. The kids loved the pool and the fenced yard provided a private oasis for sitting outside on the lanai. To accommodate all the kids one grandchild slept on a mattress on the floor in the bunk room, but they loved being all together on one room. Napili beach was just a three-minute walk from the house and great for sitting on...
NEW Construction! Just Steps from Maui's Best Beach!
Private kitchen | Fridge, microwave, oven, stovetop
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
9.8 out of 10, Exceptional, (46)
"This a great property that functions well for large events. The rooms are laid out hotel style so plenty of privacy with a large common room and kitchen on the top floor. The pool, gym, and theater are a definite bonus. The property has a short private path that opens onto a public beach. I cant recommend this place enough."
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
Beach nearby
Modern 3 Bedroom Tropical Kihei Home Near Beach
9.8 out of 10, Exceptional, (133)
"Lovely home in Kihei, well appointed, modern and comfortable. Easy walking distance to beaches, restaurants and the food trucks at South Maui Gardens!"
Modern 3 Bedroom Tropical Kihei Home Near Beach
Fridge, microwave, oven, stovetop
HOUSE.. ON THE BEACH MAUI
9.8 out of 10, Exceptional, (137)
"Brian was exceptionally helpful from the get go. The house was perfect for our extended family and had all the amenities we needed for wonderful days at the beach. The kitchen was well appointed and clean, with plenty of plates, utensils, and cooking gadgets. The outdoor space was perfect for our little ones to run and play. There was even a little kiddie pool, ideal for after-beach splashing. We enjoyed the lanai every day for cards games, lunch, dinner, and gathering. It was a great location...
HOUSE.. ON THE BEACH MAUI
On the beach
The Best of the Best JUST GOT BETTER with 3rd Remodel
9.8 out of 10, Exceptional, (205)
"We had a wonderful stay at this Maui property. The unit was just as depicted, and was a perfect fit for our family of 5, plus Grandma. All the necessary kitchen items were there to make everything that we desired, and were in relatively good shape. The unit also had beach chairs, umbrella, boogie boards, and a cooler to make our daily excursions to the beach that much more fun. The property had a decent pool, and the kids really enjoyed the outdoor shuffleboard and putting green that was first...
The Best of the Best JUST GOT BETTER with 3rd Remodel
On the beach, sun loungers, beach towels
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
9.8 out of 10, Exceptional, (178)
"We loved our stay here! Our family of 17 had plenty of room and the house is very well stocked! We enjoyed being across from a great beach and absolutely loved having our own pool. We would stay here again in a heartbeat!"
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
Pool | Outdoor pool, a heated pool
Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach
9.8 out of 10, Exceptional, (128)
"The house and location were perfect for our family of 10. The neighborhood was quiet and a very short drive or 10 min walk to the beach. There was ample public parking next to the beach which was excellent for snorkelling. The pool was ideal for our 4 grandchildren and the house was beautiful and exactly as shown in the VRBO web site. Daniel was an excellent host and very responsive. We shall definitely return there"
Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach
On the beach
Stunning Beachfront Private Home! Perfect for Families, Great Location!
9.8 out of 10, Exceptional, (89)
"We had a wonderful time at Halama House-it is exactly as advertised. Being able to walk a few steps to the beach each night for the sunsets was wonderful and being able to sit on the lanai and eat even with the wind blowing was a plus. The house is large, had comfortable furniture, a well equipped kitchen with plenty of supplies and we never felt crowded. The kids loved their "private pool".They have lots of beach toys but the beach chairs were locked up and we didn't think soon enough to ask...
Stunning Beachfront Private Home! Perfect for Families, Great Location!
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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.

Other property types in Olowalu

Outdoor pool
Aston Mahana at Kaanapali
3.5 star property
9.0 out of 10, Wonderful, (1467)
"Visited this hotel on my in-law recommends and it met my expectations. Courtesy staff and ready to help whatever is needed .. "
The price is $613
$753 total
includes taxes & fees
May 14 - May 15
Aston Mahana at Kaanapali
4 outdoor pools
OUTRIGGER Honua Kai Resort & Spa
4.0 star property
8.8 out of 10, Excellent, (2531)
"I loved everything about this resort. "
OUTRIGGER Honua Kai Resort & Spa
Hypo-allergenic bedding, in-room safe, blackout drapes
Aston Kaanapali Shores
3.5 star property
8.6 out of 10, Excellent, (2994)
"We had a great stay at this hotel. Yes, it's a little old but it's clean. It has a restaurant on site which serves good food and drinks. We ate there twice during our 4-night stay. The swimming pools and hot tubs are very nice and well-maintained. The staff are helpful and friendly. There are restaurants and supermarket across the street and there are also food trucks next to the hotel. Dukes is walking distance if you walk on the boardwalk and the beach. It's a nice location. It is...
The price is $263
$340 total
includes taxes & fees
May 14 - May 15
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.