Photo by Claire Houston

Holiday Homes in Olowalu

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Featured Holiday Homes in Olowalu

Kaiholo Hale

3.0 star property
9.4 out of 10, Exceptional, (186)
"A bit dated but honestly was part of its charm. Spotless & utterly comfortable. Great location. Managed well. "
Kaiholo Hale

Kapalua Golf Villas by KBM Resorts

3.5 star property
10.0 out of 10, Exceptional, (3)
"Privacy was very important to me. "
The price is AU$1,423
includes taxes & fees
8 Dec - 9 Dec
Kapalua Golf Villas by KBM Resorts

Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!

10.0 out of 10, Exceptional, (2)
"If you seek a large home that can accommodate large groups, if you seek close proximity to the most amazing beach - this is the home for you! It feels like Napili Bay is in your front yard! Napili Bay has long been our favorite beach on all of Maui, and now we finally have a home next to it, that we can return and rent each year. We had small kids, teens and adults and the home and management just couldn’t be better. 5 stars all the way around."
Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!

Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!

10.0 out of 10, Exceptional, (3)
"We had our whole family with us in Hawaii and it was wonderful! This home was perfect for us- each little family with their own room and bathroom. The pool was perfect for the grandkids and the adults loved the fitness room. Napili Bay beach was so close and convenient for our kids young families. It was the best family vacation we’ve ever taken. "
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!

OCEANFRONT HOME*UNINTERRUPTED*HOT TUB*PRIVATE GEM

9.6 out of 10, Exceptional, (5)
"Our family of 4 (boys ages 19 and 15) stayed here on our Maui stretch of an island hopping vacation. Wish I could have stayed here longer- truly a special place! Home is private, has amazing views, comfortable beds and super convenient to everything. Mahalo for making our vacation wonderful!"
OCEANFRONT HOME*UNINTERRUPTED*HOT TUB*PRIVATE GEM

Privacy In Paradise - Top Rated Vacation Home in West Maui

10.0 out of 10, Exceptional, (128)
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Privacy In Paradise - Top Rated Vacation Home in West Maui

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.

Island Surf with Ocean View - Across from popular Surf spot, Beach, and Shops

9.8 out of 10, Exceptional, (69)
"We had a great stay. Location was great, across from one of the most popular surfing beaches. Beautiful sunrises and sunsets everyday. Overall, would stay again."
Island Surf with Ocean View - Across from popular Surf spot, Beach, and Shops

Kihei Akahi A108: Kamaole Beach II Ocean View Town House directly across street.

9.2 out of 10, Wonderful, (49)
"This property was everything we hoped it would be, and more! Centrally located, steps from the beach, shops, groceries, gear rentals, and a spectacular view overlooking one of the best beaches in Kihei. We didn't miss a sunset, either from the lanai or the beach. Kamaole Beach II is the perfect location. Lots of fun sand, boogie boarding on stormy days and right beside good snorkeling on calmer days on Beach III. As for the unit: Plenty of beach gear (chairs, umbrellas, snorkeling gear and...
Kihei Akahi A108: Kamaole Beach II Ocean View Town House directly across street.

#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool

2.0 star property
10.0 out of 10, Exceptional, (3)
"This is truly an exceptional property, if I could give it 6 stars I would. It had everything you could possibly need for a Maui vacation. The upstairs has a game room equipped with ping pong, air hockey and video games that would rival most arcades. The fitness facility was as well equipped as the fitness center we work out at in Denver. The bedrooms, bathrooms, kitchen and living areas are all beautiful and spacious, way more than enough room for our group of 12. There are tons of beach chairs,...
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool

The #1 Luxury OCEAN FRONT Mansion! Sleeps 32

9.8 out of 10, Exceptional, (58)
"Great place to stay with a large group. Place presented just like the pictures. We had 20 adults and 12 kids ranging from 3 months to 13 years in our group. Everyone had more than enough space and privacy when needed. The management group was quick and attentive to all of our needs/requests. The kids didn't want to leave, The group can't wait to come back."
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32

Private gated home with 300 Foot private beach front, beach toys and much more!

10.0 out of 10, Exceptional, (53)
"Wonderful location on a secluded beachfront. Great indoor and outdoor spaces. All amenities you could want. Off street parking. Comfortable beds. Easy communication with property owner "
Private gated home with 300 Foot private beach front, beach toys and much more!

The Best of the Best JUST GOT BETTER with 3rd Remodel

9.8 out of 10, Exceptional, (210)
"Our family of 10 (11 when you count our infant granddaughter) had a wonderful time at Brian’s place. The condo was clean and suited our needs just great! There were plenty of beds for all of us! The kitchen was stocked well including spices and such from other guests to get us started. Plenty of soaps, shampoos, toilet paper.and laundry soap. So many nice touches. Papakea resort was beautiful as well. The kids loved the swimming pool! The beach steps away had shady spots while we played in the...
The Best of the Best JUST GOT BETTER with 3rd Remodel

Summit Residence at KAANAPALI VISTA~4500 sf~5B/5.5B Pool/Ocean View~

10.0 out of 10, Exceptional, (123)
"House was amazingly appointed. Everything we could have needed was accounted for. Great location too! Could not have asked for more! "
Summit Residence at KAANAPALI VISTA~4500 sf~5B/5.5B Pool/Ocean View~

Lana’i Oasis and Gem, The Artist's House

10.0 out of 10, Exceptional, (177)
"We had such a nice time enjoying this lovely home and its beautiful patio and garden. We spent most of our time exploring the island after reading all the information that is located in a book put together by the owner. Comfortable beds! "
The price is AU$1,228
includes taxes & fees
2 Dec - 3 Dec
Lana’i Oasis and Gem, The Artist's House

Maui Breeze Retreat Ho'olei open Dec 7-15, Jan 7-16, Jan 24-Feb 1, Feb 26-Mar 15

10.0 out of 10, Exceptional, (125)
"The property was even better in person and obviously well cared for. It was spacious, well appointed, and had an excellent Wailea location. Would gladly stay again. Thank you for such a memorable trip!"
Maui Breeze Retreat Ho'olei open Dec 7-15, Jan 7-16, Jan 24-Feb 1, Feb 26-Mar 15

Beautifully Remodeled 3bedrooms/2bathrooms

9.8 out of 10, Exceptional, (32)
"The property was clean and perfectly placed. We had just enough room and the beds were quite comfy. We were only minutes from beaches, golf courses, shopping and grocery stores. This was exactly what we were looking for and the price was a great value. "
Beautifully Remodeled 3bedrooms/2bathrooms

Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center

9.8 out of 10, Exceptional, (90)
"No other word but perfect amenities , size, location Pool. I have nothing bad to say"
Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center

Fantastic Ka'anapali home with pool! Great for families! Last minute specials!

9.6 out of 10, Exceptional, (37)
"Property was described perfectly. "
Fantastic Ka'anapali home with pool! Great for families! Last minute specials!

Stunning Two Story Townhouse located in Ekahi Village!

10.0 out of 10, Exceptional, (29)
"We have stayed in Ekahi Village for many years and noticed this unit as we walked up and down the grassland property of Ekahi Village to the Ocean. We booked our month long stay and we were not disappointed. This unit has the best overall view of the Ocean from the patios. Others like us used to stop and ask "tell us about this unit." Its spacious and the layout lives large The Unit has updates where needed but has kept the old world charm of its original owners. The beds are comfortable...
Stunning Two Story Townhouse located in Ekahi Village!
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

3.5 star property
8.6 out of 10, Excellent, (3350)
"The resort is pretty. The condo was clean, furnishings lovely, bed comfortable, had washer/dryer which was great and kitchen well-stocked. Would highly recommend staying there."
The price is AU$696
includes taxes & fees
10 Dec - 11 Dec
Aston Kaanapali Shores

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2627)
"Some things were not working in our room, e.g. master bedroom balcony door would not open, table in the balcony was very wobbly, dryer was not operating properly. All these issues were resolved by the staff when I called them, but they seem to be basic checks that property management should have checked before giving us keys and not have me call about them. "
The price is AU$1,148
includes taxes & fees
18 Dec - 19 Dec
OUTRIGGER Honua Kai Resort & Spa

The Westin Ka'anapali Ocean Resort Villas

4.0 star property
8.6 out of 10, Excellent, (1080)
"overall good experience "
The price is AU$868
includes taxes & fees
11 Dec - 12 Dec
The Westin Ka'anapali Ocean Resort Villas
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.
Beautiful view of the beach with palm trees

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