Photo by Claire Houston

Search Vacation Homes in Olowalu

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
14 Rab. I - 16 Rab. I
In two weeks
21 Rab. I - 23 Rab. I
In one month
4 Rab. II - 6 Rab. II
In two months
2 Jum. I - 4 Jum. I

Compare 358 Vacation Homes in Olowalu with updated reviews, rates, and availability.

Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
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, (193)
"If you are looking for a group gathering, this is the place. Location, and all other desires were right there.We were there during the last storm (Jan 2025), and did have some leaks and flooding, but that doesn't change how we felt about staying there. No one can predict the weather!I want to thank the property owner for offering such a beautiful place to vacation!!LB"
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
Spectacular Maui Family vacation home - 4 bedroom + den, 4 bath, AC, pool.
Miscellaneous

Spectacular Maui Family vacation home - 4 bedroom + den, 4 bath, AC, pool.

9.8 out of 10, Exceptional, (33)
"We absolutely loved our time here and will definitely be back. Could not have been a prettier location."
Spectacular Maui Family vacation home - 4 bedroom + den, 4 bath, AC, pool.
Maui Breeze Retreat at Ho'olei! Openings March 15-21, May 12-17 & June 6-13!
Sun loungers

Maui Breeze Retreat at Ho'olei! Openings March 15-21, May 12-17 & June 6-13!

10.0 out of 10, Exceptional, (128)
"Beautiful home! Great location! We had a great week on our annual family vacation, this was our first with new babies. We ran into a small issue when checking in, but all was taken care of quickly. We are planning on doing this trip every year and hope to be able to stay in same home again!"
Maui Breeze Retreat at Ho'olei! Openings March 15-21, May 12-17 & June 6-13!
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
Interior

The #1 Luxury OCEAN FRONT Mansion! Sleeps 32

9.8 out of 10, Exceptional, (67)
"We had a fantastic time! Everything was even better than we expected. We only wish we’d had a little more sunshine"
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
Kaiholo Hale
Beach nearby

Kaiholo Hale

3.0 star property
9.4 out of 10, Exceptional, (195)
"A perfect area and a perfect stay! The hosts think of everything and even include some nice touches like banana bread and chocolates. The property is immaculate and the condo is extremely comfortable. We would recommend this property to anyone."
Kaiholo Hale
105-1 Puamana Spacious Townhome Near Ocean.
Pool

105-1 Puamana Spacious Townhome Near Ocean.

9.4 out of 10, Exceptional, (52)
"We checked out of this beautiful condo three days before the Maui fires. It was one of those places where we for sure will come back to. As far as I can tell, it is still standing, but the clubhouse and some surrounding buildings did burn. This is the most amazing location on the island. Will definitely be back hopefully to help rebuild, and for sure to enjoy the beauty."
105-1 Puamana Spacious Townhome Near Ocean.
Oceanfront All-Suite Escape with AC & Pool | Steps to Sand | Walk to Dining
Miscellaneous

Oceanfront All-Suite Escape with AC & Pool | Steps to Sand | Walk to Dining

8.8 out of 10, Excellent, (12)
"My family was super excited about the place and location of the Condo but when we arrived at the property the dishwasher and ice machine in the fridge did not work and when we contacted Vacasa they said it was an owner issue. The plates and mugs and silverware were not clean from the outset so we hand washed every item before using it. We then hand washed after every meal. ( There were 6 of us so a ridiculous amount of vacation time was spent at the sink!) The condo is in an amazing location but...
Oceanfront All-Suite Escape with AC & Pool | Steps to Sand | Walk to Dining
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!
Beach nearby, sun loungers, beach towels

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

10.0 out of 10, Exceptional, (9)
"Beautiful"
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!
Summit Residence at KAANAPALI VISTA~4500 sf~5B/5.5B Pool/Ocean View~
Miscellaneous

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

10.0 out of 10, Exceptional, (130)
"We were looking for a house that could accommodate 5 couples, with great outdoor space and within walking distance to the beach and shopping/restaurants. The Summit Residence did not disappoint! The house was clean and spacious with a well equipped kitchen. Lower level game room was nice and having a second full size fridge was awesome for storing drinks or overflow. We used the grill multiple times. The lanai and pool were perfect. Used daily! Plenty of extras included with the house. ...
Summit Residence at KAANAPALI VISTA~4500 sf~5B/5.5B Pool/Ocean View~
87-1 Escape to Paradise at Puamana's Hale Nalu
Pool

87-1 Escape to Paradise at Puamana's Hale Nalu

10.0 out of 10, Exceptional, (21)
"Loved our stay in Lahaina. The property managers were so gracious and happy to have guests back after fire and wanted us to let them know what might be needed. They were great about taking care of the few things we found. Reading some of the previous previews from before - wanted to say, there is a flashlight in closet, 4 beach chairs, 2 recliners (anti-gravity) 3 boogie boards, cooler...all of which we enjoyed. the pool was just a few houses down and very comfortable and relaxing. Really...
87-1 Escape to Paradise at Puamana's Hale Nalu
Kapalua Golf Villas by KBM Resorts
Condo, 2 Bedrooms, Balcony, Resort View (21p2) | Beach/ocean view

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 SAR 3,033
SAR 5,596 total
includes taxes & fees
12 Mar - 13 Mar
Kapalua Golf Villas by KBM Resorts
Location, Location.... Just Steps Away from the Ocean!
Pool

Location, Location.... Just Steps Away from the Ocean!

9.6 out of 10, Exceptional, (134)
"This was an amazing location, so close to Lahaina & easy to get throughout the island. The condo supplies in the kitchen were great. We found this to be a great stay. If I were to be very nitpicking, the bathroom fan was very dusty & got me thinking maybe what else was dirty, however I saw nothing else. The pools need a bit of love that are in the complex, but the oceanside one was so amazing that the love that is needed to it does not even matter. I would say this is one of the best pools I...
Location, Location.... Just Steps Away from the Ocean!
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool
Outdoor pool

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

2.0 star property
10.0 out of 10, Exceptional, (6)
"Wonderful experience!. Accommodated 26 people with no problem at all. Beautiful house!"
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool
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, (215)
"I have stayed in many rental homes and this is by far the best equipped rental home I have ever stayed in. We love to cook and usually can’t find enough pots and pans and utensils and this house had them all.We also had the privilege of their neighbors having goats and baby goats and cows which we enjoyed seeing from the deck of the house The house was also close enough to major towns And easy to find I would definitely stay here again on our next trip to Maui "
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC
Outdoor dining

Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC

10.0 out of 10, Exceptional, (115)
"Finding this property that accommodated multiple family members was a gem. The dual-level bedroom layout and the additional cottage for young couples offered both privacy and togetherness—a perfect combination for family gatherings. A well-stocked kitchen and large gathering space is indeed a boon, making group meals and celebrations seamless. Staying within walking distance to local amenities and enjoying breathtaking sunsets each evening was delightful. Witnessing over 13 sea turtles coming...
Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC
Charming 3 BR Puamana Oceanfront in private gated community
Property grounds

Charming 3 BR Puamana Oceanfront in private gated community

9.6 out of 10, Exceptional, (105)
"Comfy beds, lots bathrooms, well stocked kitchen in a georgous location. Paradise! "
Charming 3 BR Puamana Oceanfront in private gated community
The Best of the Best JUST GOT BETTER with 3rd Remodel
Smart TV, DVD player, books, stereo

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

9.8 out of 10, Exceptional, (214)
"The resort is its own oasis, from playing in the sand to swimming in the pool. The room had everything we needed, you know when you say, I wonder if they gave this or that...the answer was yes. The resort has activities each day, a Mai Tai hour. We had all the ammenities we needed. We arrived late so lots closed but we were prepared. You dont get a lot of noise from neighbors, the staff are super nice and helpful. 10 out of 10 stay! "
The Best of the Best JUST GOT BETTER with 3rd Remodel
Private home with POOL & OCEAN VIEWS near BEAUTIFUL KAANAPALI BEACH
Outdoor pool, a heated pool

Private home with POOL & OCEAN VIEWS near BEAUTIFUL KAANAPALI BEACH

9.6 out of 10, Exceptional, (58)
"We had a wonderful vacation here! The home is beautiful, we loved the pool, and really appreciated all the activity gear that’s available on site (snorkel gear, life vests, pool floats, bodyboards!). We hope to stay here again next time we travel to Hawaii "
Private home with POOL & OCEAN VIEWS near BEAUTIFUL KAANAPALI BEACH
CLOUD 9 BEACH HOUSE, Walk to Beach, Oceanview. Many Amenities, Very Clean, Legal
Fridge, microwave, oven, stovetop

CLOUD 9 BEACH HOUSE, Walk to Beach, Oceanview. Many Amenities, Very Clean, Legal

9.8 out of 10, Exceptional, (74)
"Great property with perfect location, very relaxing. It was a short driving distance to beaches, restaurants, shops- less than five minutes. Pool is not heated but warms up in the afternoon (during winter). "
CLOUD 9 BEACH HOUSE, Walk to Beach, Oceanview. Many Amenities, Very Clean, Legal
3BD NEW! Luxurious, Newly Remodeled, Walk to beach
Interior

3BD NEW! Luxurious, Newly Remodeled, Walk to beach

10.0 out of 10, Exceptional, (51)
"Clean, well appointed, safe, and an easy walk to a beautiful beach. Home was as advertised. Excellent communication. Highly recommend. "
3BD NEW! Luxurious, Newly Remodeled, Walk to beach
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.
Don't see what you're looking for?
See all available properties in Olowalu
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Olowalu

Aston Kaanapali Shores
2 outdoor pools, pool umbrellas, sun loungers

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3479)
"Thank you! Loved it!"
The price is SAR 938
SAR 1,217 total
includes taxes & fees
14 Mar - 15 Mar
Aston Kaanapali Shores
OUTRIGGER Honua Kai Resort & Spa
4 outdoor pools, open 8:00 AM to 10:00 PM, cabanas (surcharge)

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2718)
"Great location. Easy access to multiple pools and beach. Outstanding for family. "
The price is SAR 1,242
SAR 3,452 total
includes taxes & fees
4 Apr - 5 Apr
OUTRIGGER Honua Kai Resort & Spa
Aston Maui Kaanapali Villas
Exterior

Aston Maui Kaanapali Villas

3.0 star property
8.6 out of 10, Excellent, (2358)
"It's a beautiful location, near easily walkable spots and perfect for people with small children. The pool could be bigger, but if you have a child younger than 3 years old, it's a perfect size. Lots of other wonderful guests to hang out with."
The price is SAR 919
SAR 1,416 total
includes taxes & fees
11 Mar - 12 Mar
Aston Maui Kaanapali 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.