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Check prices for these dates

Next weekend
7 Saf. - 9 Saf.
In two weeks
14 Saf. - 16 Saf.
In one month
28 Saf. - 2 Rab. I
In two months
28 Rab. I - 30 Rab. I

Compare 260 Vacation Homes in Kahakuloa with updated reviews, rates, and availability.

Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A
One of the largest condo pools in Kihei!

Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A

9.6 out of 10, Exceptional, (92)
"The property and grounds were clean and family friendly."
Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A
Spacious Family Beach House with Large Heated Pool; walk to Beach 🏖
Pool

Spacious Family Beach House with Large Heated Pool; walk to Beach 🏖

10.0 out of 10, Exceptional, (126)
"Had a blast. "
Spacious Family Beach House with Large Heated Pool; walk to Beach 🏖
272-1 Large oceanfront home- fully air conditioned, 25 feet from the water

272-1 Large oceanfront home- fully air conditioned, 25 feet from the water

9.0 out of 10, Wonderful, (38)
"The rental had multiple disappointing issues. Some are listed: the house had cockroaches, centipedes, spiders and ants in the kitchen and bathrooms. The AC didn’t work twice during our stay. The master bedroom had no door or windows that opened. The AC in the master bedroom barely worked. We relied one the room fan for air circulation. The rental was bare minimum cheap on supplies, considering how much we paid for 21 days stay! "
272-1 Large oceanfront home- fully air conditioned, 25 feet from the water
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
Exterior

The #1 Luxury OCEAN FRONT Mansion! Sleeps 32

9.8 out of 10, Exceptional, (64)
"Great location between Kaanapali and Kapalua. Private sleeping quarters, media room, gym, nice top floor communal area with a view of the ocean. Watched whales breach from inside the house. Sea turtles on the beach. There are lots of stairs, but as long as you are able to climb them it’s not an issue. Would definitely recommend for those traveling with a large group. "
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
Stunning Beachfront Private Home! Perfect for Families, Great Location!
Amazing Lanai~ Kick Back~ Relax and Enjoy the View!

Stunning Beachfront Private Home! Perfect for Families, Great Location!

9.8 out of 10, Exceptional, (93)
"11 family members stayed at this property. Beautiful yard, view of ocean, access to beach, great location."
Stunning Beachfront Private Home! Perfect for Families, Great Location!
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, (7)
"Great spaces to accommodate a large family including a large kitchen, multiple bedrooms and bathrooms, lanai dinning"
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!
Spectacular, fully renovated 3-Bedroom Oceanfront Townhome in Kahana
Outdoor dining

Spectacular, fully renovated 3-Bedroom Oceanfront Townhome in Kahana

10.0 out of 10, Exceptional, (63)
"We stayed in Kahana with our children and their families. Six adults and three kids under 6 in this beautifully styled, waterfront property. The condo was beautifully and thoughtfully appointed with everything we needed. Clean, quiet and modern unit situated on a beautiful property. Pool and grounds are spotless and offer magnificent views of the islands, whale spouts and swimming sea turtles. Our hosts were helpful, considerate and easy to communicate with. Thank you Tracy and Steve for a...
Spectacular, fully renovated 3-Bedroom Oceanfront Townhome in Kahana
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool
Exterior

#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 Vacation Rental on Maui!! Steps to Maui's Best Beach!
Private pool with in pool sunbathing shelf and slide.

The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach!

10.0 out of 10, Exceptional, (88)
"This house is beautiful, layout was perfect for our family of 17. Short walk to one of the best beaches in Maui, cute coffee shops, restaurants and beach rentals. Communication was great with property management. House was very well organized and one of the best features was the laundry room with 3 washers and 3 dryers! Will definitely be one of our best memories "
The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach!
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
Our heated pool with the beach just 50 feet past our lava rock wall.

Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre

9.8 out of 10, Exceptional, (192)
"This property was a good fit for family of our kids, spouses, and grand kids - 15 total. It would have been more comfortabIe if the house had air-conditioning in the kitchen and living room-dining room. We spent lots of time on the large patio eating meals, playing games and making memories!"
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
Private home with POOL & OCEAN VIEWS near BEAUTIFUL KAANAPALI BEACH
Exterior

Private home with POOL & OCEAN VIEWS near BEAUTIFUL KAANAPALI BEACH

9.6 out of 10, Exceptional, (57)
"The stay was great. "
Private home with POOL & OCEAN VIEWS near BEAUTIFUL KAANAPALI BEACH
Secluded Ocean View Napili Home - Sleeps 14
Exterior

Secluded Ocean View Napili Home - Sleeps 14

10.0 out of 10, Exceptional, (57)
"House was great for extended family trip."
Secluded Ocean View Napili Home - Sleeps 14
Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!
Pool

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

10.0 out of 10, Exceptional, (3)
"Great stay! Had everything we needed for 8 adults. Close to ocean and groceries….wish we didn’t have to leave!"
Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!
105-1 Puamana Spacious Townhome Near Ocean.
Dining Room and Family Room looking out to Lanai

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.
Private gated home with 300 Foot private beach front, beach toys and much more!
Our very own beach

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

10.0 out of 10, Exceptional, (57)
"The property is everything and then some. Gorgeous sunset views, ample outdoor space and plenty of places to sit eat or play outdoor games. The house is very well equipped. All of the rooms are very generously sized and having incredible ocean views. Our house could not have been nicer and responded to everything almost immediately. We can’t wait to come back!"
Private gated home with 300 Foot private beach front, beach toys and much more!
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
Back yard view w/ Lots of Lushes Green Grass to enjoy the breath taking views.

Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

10.0 out of 10, Exceptional, (212)
"Stunning and immaculate country home perfect for your Maui adventure. Comfortable and beautiful accommodation centrally located to all attractions. We would stay here again 💯! "
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
Living area

Spacious Maui Beach House, Private Pool, AC, Sleeps 6

10.0 out of 10, Exceptional, (45)
"Wonderful, clean accommodations with everything you need. Amber and Jeremy were wonderful hosts—ready and willing to help if needed. Very close to the beach in a wonderful location. Couldn’t be happier. "
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
BEACHFRONT HOUSE KIHEI, MAUI..TRUE HAWAIIAN HOME 1960's
80780ad6-2e03-45fe-a188-3a1ff2f62c63

BEACHFRONT HOUSE KIHEI, MAUI..TRUE HAWAIIAN HOME 1960's

9.8 out of 10, Exceptional, (97)
"We truly enjoyed the beach house! The sunsets were amazing! "
BEACHFRONT HOUSE KIHEI, MAUI..TRUE HAWAIIAN HOME 1960's
Beautifully Remodeled 3bedrooms/2bathrooms
Beach across the street

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
Sugar Beach Resort condo with ocean view, AC - surf, bike & golf

Sugar Beach Resort condo with ocean view, AC - surf, bike & golf

8.8 out of 10, Excellent, (46)
"The location can’t be beat. Spectacular sunset in a quiet environment. Everything you need is here. Had the best time ever. If I had to find a negative I’d say the couch is uncomfortable but that it. Will be back for sure Highly recommend. "
Sugar Beach Resort condo with ocean view, AC - surf, bike & golf
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 Kahakuloa

Aston Kaanapali Shores
Exterior

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3436)
"We were pleasantly surprised at about this resort. First off, receiving the Expedia gold upgrade was amazing!! Received a huge 2300 sf 2 bedroom suite with a wraparound oceanfront deck. Just sitting on the deck with the waves at the shore was a highlight of our trip! The facility had all that we needed and was right across the street from grocery/pharmacy and had a food truck area every night with great food. The restaurant at the hotel was also very good, and we loved that there was a bar...
The price is SAR 1,346
SAR 1,698 total
includes taxes & fees
30 Jan - 31 Jan
Aston Kaanapali Shores
Kaanapali Alii
Pool

Kaanapali Alii

4.0 star property
9.6 out of 10, Exceptional, (857)
"Beautiful accommodations."
Kaanapali Alii
OUTRIGGER Honua Kai Resort & Spa
Exterior

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2682)
"We enjoyed our stay at the Honua Kai Resort and Spa. It's location was ideal for us. The studio was the perfect size for the two of us, and loved having the kitchenette for simple fixings. The balcony had a lovely view, and feel that the location to the beach and to Duke's made everything so easy. The bed/pillows were quite comfortable and easy access to valet parking. The parking valets were all very friendly and helpful for suggestions or directions."
The price is SAR 1,401
SAR 3,639 total
includes taxes & fees
28 Jan - 29 Jan
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.