On the back side of Haleakala crater is Kaupo, the drive is spectacular and quite different from the rest of the island. the ocean to one side and the volcano on the other. Take it slow and enjoy the drive. #GoldenHour

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Vacation Homes in Kaupo

"The property was excellent, highly recommend. "

SAR 1,336 total

includes taxes & fees

11 Aug - 12 Aug

"Loved the location, there was even a peek-a-boo view of Hāna Bay. Lovely garden. "

SAR 1,489 total

includes taxes & fees

18 Aug - 19 Aug

"This house is beautiful and we loved everything about our stay. It's in a great location to spend time exploring the Road to Hana. We can't wait to come back!"

SAR 2,480 total

includes taxes & fees

28 Jul - 29 Jul

Beach nearby, sun loungers, beach towels

"Located a few miles beyond Hana, this is a well-equipped and very comfortable rental. "

"Stunning and immaculate country home perfect for your Maui adventure. Comfortable and beautiful accommodation centrally located to all attractions. We would stay here again 💯! "

"16 of us stayed at this beautiful property. Two Families, 12 children total. We have nothing bad to say. All of our expectations were met. The listing is true and accurate. Communication with the property manager was always prompt and efficient.We would definitely stay her again."

SAR 11,093 total

includes taxes & fees

11 Aug - 12 Aug

"We had a great time. Location is beautiful. House is comfortable, clean, and well-equipped. The view is amazing. Pool and whirlpool were a hit. Close to stores/restaurants in Makawao. Good hiking nearby. The hosts were responsive and helpful. Really can’t say enough about the views. I spent more time enjoying the views than reading my book! Didn’t even think about turning on the TV!"

"Neat clean lots of amenities "

"For Hana, this was a great find. AC in both bedrooms. Nice porch with a great view. Full kitchen. Modern rain shower was great after the long drive. Check and out was easy. "

"We had the best time at our VRBO. The house was beautiful. The host was so accommodating. They answer our text right away. The pool was amazing. We would definitely book here again."

"Great location for family gathering. Close to many amenities. "

On the beach, sun loungers, beach towels

"Excellent all around property"

"Well situated close to local food trucks and general store. The unit had all the amenities for cooking and chairs and umbrellas for the beach. Excellent balcony with ocean views and parking for two cars. "

"This property is amazing! Not right on the water but great view of the ocean, can hear the ocean and 3minute walk to the beach!! Beautiful property and plenty of extras such as a jacuzzi, sauna, boogie boards, beach chairs, beach toys for the kids, and an on-site private outside shower to clean up after walking or playing in the beach. "

SAR 5,176 total

includes taxes & fees

8 Aug - 9 Aug

"We spent an amazing week here. If you are looking for peace and quiet with a stunning view and gracious hosts, this is the place! We will definitely stay here again!"

"There could not be a better house with a better view The yard itself is breathtaking The pictures are perfect on this site Martha was very attentive a came to our every need . Very clean place and kitchen has every appliance and utensils you could want. The concierge Martha referred us to was Dona and she booked everything for us. Thank you "

"Lovely home with everything we would ever need. Wonderful hosts"

"The architecture and view were absolutely amazing and the house was perfect for our family. The outdoor spaces were ideal - loved the infinity pool! There were some minor issues during our stay, but the host was very attentive and quick to respond. I am confident that the owner has already handled the few remaining items. Our family is very excited to come back to this beautiful home. "

"This place was a dream. Such a lovely property walking distance to beaches and a short drive into Hana. Would recommend to anyone looking to get away. "

"Wanted a place for my family to stay while we enjoyed the road to Hana in Maui. This place checked the boxes. "

SAR 2,476 total

includes taxes & fees

8 Aug - 9 Aug

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Top Kaupo Hotel Reviews

Luxury Upcountry Villa with breathtaking views

10/10 Excellent

"We had the most amazing experience in Hawaii and was mostly due to where we stayed! David and Dawn were the most amazing hosts! Very responsive and helpful with restaurants, things to do and made our stay very comfortable! This place was perfect for our family of 5 and the views - stunning!! We plan to come back and know exactly where we would stay!! "

Hotel Wailea, Relais & Chateaux - Adults Only

10/10 Excellent

"It was an amazing boutique resort the property is beautiful and very relaxing a different vibe from the other Wailea resorts the staff is great and the amenities are nice including the shuttles to anywhere in the Wailea area. Definitely would come back and say if you get a chance to check it out loved our suite"

Beautiful Condo, Private Lanai, Near Wailea Beaches

10/10 Excellent

"Wailea Grand Champions Condo was perfect location to stay near family gatherings and events while in Maui for Mom’s ashes to sea ceremony. The condo was clean, quiet, spacious and well worth the price. I enjoyed the privacy of the two rooms and the lanai. We would definitely choose this location again. Thank you! "

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

10/10 Excellent

"Clean, comfortable, modern, calm friendly setting with amazing views. Tasey the owner/manager was kind, caring easy to talk to and work with. Thank you so much for sharing your beautiful home. Wmy grandkids were ready to move in permanently The home is well furnished and I would highly recommend to anyone We loved the quaintness of Makawao"

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Vacation Homes in Kaupo

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Fisher's Hana Bay Hale, Across from Hana Bay

Romantic Hana Hideaway, Big Ocean Views, Old Hawaii Charm

IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

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

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Exceptional Upcountry Villa with breathtaking views

Luxurious Tropical Home with Heated Pool, 5min to Wailea Beach, Mini Split ACs!

Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

Breath taking ocean and volcano views! Pool,Close to beaches and everything else

PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING

Amazing Hana Bay Beach Cottage Location! 5-Minute Walk to Hana town & beaches!

Hana Bay View 3 BR/2 BA house sleeps 6 comfortably with 2 patios.

Hana Homestead by the Beach

Kula Luxury Retreat With Stunning Ocean & Mountain Views!

Summer Deals Book now Island Retreat Spacious 3B 3B home.

Stunning views! Exclusive pool, spa and big private yard.

One-of-a-Kind Maui Getaway!

Breathtaking Oceanfront Location, Gorgeous Views, Stroll to Hamoa Beach, Hot Tub

Beautiful Home in paradise!

Top Kaupo Hotel Reviews

Luxury Upcountry Villa with breathtaking views

Hotel Wailea, Relais & Chateaux - Adults Only

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Breath taking ocean and volcano views! Pool,Close to beaches and everything else

Beautiful Condo, Private Lanai, Near Wailea Beaches

Fisher's Hana Bay Hale, Across from Hana Bay

IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

Hawaiian Cottage and Personal Paradise /BBKM 2013/0004

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

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