Search Vacation Homes in Kaupakulua

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Compare 196 Vacation Homes in Kaupakulua with updated reviews, rates, and availability.

Kaiholo Hale
3.0 star property
9.4 out of 10, Exceptional, (185)
"We had a great time, and I hope I can go back, I am so happy 😊 "
Kaiholo Hale
WOW! Stunning Ocean Views, Large Deck &Luxury Beds
10.0 out of 10, Exceptional, (41)
"What a view! We watched the sunset every night from the patio. The space was very large and also very well equipped with beach gear. A/C worked great and no issue with any part or the property."
WOW! Stunning Ocean Views, Large Deck &Luxury Beds
Private & Fabulous views! Exclusive pool, spa and 1 acre yard
10.0 out of 10, Exceptional, (123)
"The property provided us ample space to spread out and relax"
Private & Fabulous views! Exclusive pool, spa and 1 acre yard
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
10.0 out of 10, Exceptional, (77)
"We had a wonderful time staying at the Umalu location. It was conveniently located right next to the highway so it was easy access to get around the island. And it was only a 5 minute drive down the street from the beach. The hosts, Kelly and Dan were so nice and made us home made banana bread to welcome us and also shared some great dining locations for us to visit during our stay. "
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
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 !!!
Mountain to Ocean Views Pole House @ Maui Adventure Villa
9.8 out of 10, Exceptional, (206)
"We were amazed at the warmth and decor and incredible views from this beautiful home We would not hesitate to return. Jeff and Beth"
Mountain to Ocean Views Pole House @ Maui Adventure Villa
Private Luxury Villa in Kihei. Just moments walk to the beach. 10/10 reviews!
10.0 out of 10, Exceptional, (27)
"The pictures don’t do the property justice along with a great host. Our family had the most enjoyable time. "
Private Luxury Villa in Kihei. Just moments walk to the beach. 10/10 reviews!
Modern 3 Bedroom Family Friendly Kihei Home Near Beach
9.8 out of 10, Exceptional, (138)
"Wonderful location with plenty of amenities to make for a great Maui vacation. In-laws booked the 2nd unit next door and we had a wonderful time hanging out on the large deck. Would absolutely book again."
Modern 3 Bedroom Family Friendly Kihei Home Near Beach
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
10.0 out of 10, Exceptional, (41)
"We had a fantastic time staying at the Kihei house. Our kids loved having their own pool and we spent hours out there everyday. The house was in a great location, everything was very clean and well taken care of. The host was very responsive when we messaged. Overall a great place to stay!"
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
9.8 out of 10, Exceptional, (68)
"We had a very relaxing time at this property! Such a beautiful place. We will definitely stay again. "
The price is AED 2,975
AED 4,930 total
includes taxes & fees
15 Nov - 16 Nov
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
Luxurious 3 Bedroom Villa at Ho'olei! Perfect for Families! Ho'olei 55-2
9.6 out of 10, Exceptional, (78)
"We came to Hawaii to visit our son and grandchildren who live in Maui. This home was perfect for our needs, well stocked, and the pool area was fantastic."
Luxurious 3 Bedroom Villa at Ho'olei! Perfect for Families! Ho'olei 55-2
Panoramic Ocean View Condo on Golf Course close to Beaches
10.0 out of 10, Exceptional, (7)
"Beautiful property with many upgrades and amazing ocean views. Great proximity to the beach and shops and a very quiet and relaxing location. The place was also very well equipped with cooking supplies, appliances and beach accessories. We would definitely stay here again!"
Panoramic Ocean View Condo on Golf Course close to Beaches
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!
BEACHFRONT MAUI KIHEI HOUSE
9.8 out of 10, Exceptional, (150)
"This house was absolutely perfect for our family. We had 10 people staying and we all fit very comfortably. The beds were nice, they have ac units in all of the rooms which was great for our family with different temperature needs. The yard was so much fun for our toddlers to run and play in and the beach is a very short walk away. We all really enjoyed relaxing at the house. We needed a pack and play for our toddler and a newborn and while we brought one we also depended on the one available at...
BEACHFRONT MAUI KIHEI HOUSE
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
9.8 out of 10, Exceptional, (187)
"We were a Party of 11 - we loved the house set up and the space was perfect for our large group - pool and beach access - awesome! "
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
Stunning Beach Front Townhouse
10.0 out of 10, Exceptional, (84)
"This property was a dream! We loved the easy accessibility to the beach, pool, restaurants, the best shaved ice, and the activities we had booked."
Stunning Beach Front Townhouse
Stunning Beachfront Private Home! Perfect for Families, Great Location!
9.8 out of 10, Exceptional, (92)
"The property is beautiful with lots of space inside and out! It is within walking distance of stores and restaurants. Stayed with a family group of 6 adults and 2 small children. The view of the beach with the grassy area and palms trees was outstanding! We played many rounds of bocce ball on the grass and the kids spent a great deal of time playing there too. Plenty of beach chairs and towels are provided as well as some sand toys for the kids. The house is a little older and dated and could...
Stunning Beachfront Private Home! Perfect for Families, Great Location!
2 Private Homes for 1! Pool & Waterslide - Cove Hale
10.0 out of 10, Exceptional, (21)
"We had a party of 10 ranging from 8-80 years old and everyone was stoked about this place. The outdoor area including the pool, outdoor showers, grill, and dining area for a lot of use from the whole family. The houses were modern, spacious, super clean, and comfortable with the crispy AC. We walked to the nearby beaches, restaurants, and food trucks with ease. The owner also lives on the property and was friendly, helpful, and happy to give recommendations of his favorite spots."
2 Private Homes for 1! Pool & Waterslide - Cove Hale
CLOUD 9 BEACH HOUSE, Walk to Beach, Oceanview, Amenities Galore, Very Clean
9.8 out of 10, Exceptional, (70)
"This is one of the best houses we have rented on vacation. Tamara has this property perfect. It’s right down the street from the beach & we so enjoyed the pool in the back yard. If we could give it a higher rating than 5 stars we would. Thank you Tamara! We hope to come back to Maui again one day hopefully soon. "
CLOUD 9 BEACH HOUSE, Walk to Beach, Oceanview, Amenities Galore, Very Clean
PRIVATE HOME-NEWLY REMODELED-AC-HOT TUB-METICULOUS CLEANING
9.8 out of 10, Exceptional, (56)
"The house is phenomenal. It had everything we needed."
PRIVATE HOME-NEWLY REMODELED-AC-HOT TUB-METICULOUS CLEANING
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

Maui Beach Vacation Club
2.5 star property
8.2 out of 10, Very Good, (699)
"Great!"
Maui Beach Vacation Club
Aston Maui Hill
3.0 star property
9.0 out of 10, Wonderful, (751)
"The apartment was beautifully decorated. Very clean. The grounds lovely, and a short distance to a strip of beach. The pool was closed for renovation, which was disappointing, as it looked beautiful and to be a respectable size. Monday night happy hour with all residents was a wonderful. treat. Drinks and food! We were the youngest in the crowd at 30's and 50's.The beds were comfortable. The kitchen has no oven and was not well equipped; we figured it out. Truly a nice place. This is located at...
Aston Maui Hill
Castle Kama'ole Sands
3.0 star property
8.0 out of 10, Very Good, (2179)
"My wife and I stayed here for our honeymoon. To say I was disappointed to come home is an understatement. Such a lovely building. Amazing location. The gardens and green space was immaculately kept and groomed. The unit we stayed in was inviting and had all the amenities we needed for an 8 day stay. Honestly it was paradise. Thank you for the lovely trip and memories that were made. We will be back. "
Castle Kama'ole Sands
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.