Search Vacation Homes in Kaupakulua

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Compare 198 Vacation Homes in Kaupakulua with updated reviews, rates, and availability.

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
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
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!
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
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
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
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
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
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
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
Ho'olei Villas | Wailea Kapili
9.6 out of 10, Exceptional, (10)
"We had a great time and enjoyed all the amenities. We had 4 kids and the bedrooms worked out perfect. Bathroom Amenities were great, Plenty of chairs, umbrellas, towels and cooler for the beach. We will be back!"
Ho'olei Villas | Wailea Kapili
Mountain to Ocean Views Pole House @ Maui Adventure Villa
9.8 out of 10, Exceptional, (203)
"We chose this place for the second half of our anniversary trip. In our travel experience, it is completely unique and absolutely worth it! Since we’re both hot sleepers, my husband and I were concerned at first that we would be too warm at night without any air-conditioning; but you open up the walls to catch the breezes, and they have fans on site, and we both slept wonderfully well. It’s an amazing place to get into the rhythm of nature: we went to sleep shortly after dark, we got up at...
Mountain to Ocean Views Pole House @ Maui Adventure Villa
Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach
9.8 out of 10, Exceptional, (74)
"Quiet and peaceful. Beautiful views."
Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
9.8 out of 10, Exceptional, (185)
"We enjoyed the space the house offered, kiddos loved the pool and adults enjoyed the lanai! The only criticism i have is in regards to the obvious active termite issue in one of bedrooms. If you choose to stay here, you will not be disappointed. "
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area
10.0 out of 10, Exceptional, (79)
"House was super clean and patio/pool were wonderful! Made our stay so easy. Beach and shopping super close. "
Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
10.0 out of 10, Exceptional, (40)
"If you are scrolling through homes and wondering where in Maui to stay and which home to choose…I would definitely recommend you stop now and book Amber and Jeremy’s place if it’s available. The location in Kihei is just perfect - there’s so much you can walk to (including Nalu’s, which has live music and my vote for best poke bowl, and trust me - I did the work). But having the water views and the beach right across the road is amazing. We would walk over to watch the sunset, and were treated...
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
CLOUD 9 BEACH HOUSE, Walk to Beach, Oceanview, Amenities Galore, Very Clean
9.8 out of 10, Exceptional, (69)
"Everything went great. Host is very accommodating and helpful."
CLOUD 9 BEACH HOUSE, Walk to Beach, Oceanview, Amenities Galore, Very Clean
Maui Breeze Retreat at Ho'olei! Available Nov. 16-24 & Dec. 7-15. Book now!
10.0 out of 10, Exceptional, (123)
"The house is what everyone said and more. Our family, my wife and I will carry many great memories from the days we spent at Steve’s house "
Maui Breeze Retreat at Ho'olei! Available Nov. 16-24 & Dec. 7-15. Book now!
Charming Direct Oceanfront North Shore Beach House
8.8 out of 10, Excellent, (27)
"We had a great time at this VRBO! It was so clean and was the perfect lay out for our family. The beds were comfortable and the views were gorgeous! We will definitely be staying again. "
Charming Direct Oceanfront North Shore Beach House
Beautiful Maui Beachfront Townhouse! Great Views! 200+ Five Star Reviews !!!
10.0 out of 10, Exceptional, (160)
"We loved our stay here - the home is cozy and the views are amazing. We enjoyed paddleboarding with turtles and seeing them not only on the beach and in the water but from the house as well. The owner and property manager were great and responsive, the home is older, but very well kept and clean. Absolutely would stay here again! No AC, but open windows and fans cooled the place down nicely, especially at night. Would highly recommend!"
Beautiful Maui Beachfront Townhouse! Great Views! 200+ Five Star Reviews !!!
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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 Kaupakulua

Wailea Ekahi - CoralTree Residence Collection
3.0 star property
9.2 out of 10, Wonderful, (484)
"Beautiful property , quiet , right on the beach !!! Couldn’t ask for more "
Wailea Ekahi - CoralTree Residence Collection
Maui Schooner Resort
3.5 star property
9.2 out of 10, Wonderful, (422)
"Our stay was wonderful. Beautiful resort and easy access to beach. Location was also good. "
Maui Schooner Resort
Sugar Beach Resort
3.0 star property
8.6 out of 10, Excellent, (1011)
"Excellent location. Condo was excellent as well"
Sugar Beach Resort
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.