Photo by Tim & Nat ✈

Search Vacation Homes in Kaupo

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Kaupo

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

9.6 out of 10, Exceptional, (379)
"Wonderful property, perfect for an overnight in Hāna."
The price is SAR 653
SAR 1,339 total
includes taxes & fees
20 Jun - 21 Jun
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Fisher's Hana Bay Hale, Across from Hana Bay

9.4 out of 10, Exceptional, (380)
"Loved everythibg about our stay! The kitchen was incredibly well stocked and spacious. Great location!"
The price is SAR 731
SAR 1,496 total
includes taxes & fees
30 Jun - 1 Jul
Fisher's Hana Bay Hale, Across from Hana Bay

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

10.0 out of 10, Exceptional, (220)
"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

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

10.0 out of 10, Exceptional, (16)
"nice place"
The price is SAR 3,207
SAR 5,008 total
includes taxes & fees
11 Jun - 12 Jun
Amazing Hana Bay Beach Cottage Location! 5-Minute Walk to Hana town & beaches!

Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

9.8 out of 10, Exceptional, (225)
"What an amazing place to stay and enjoy beautiful Hana. The home is clean, comfortable and updated. We loved the property and how well kept the landscaping - it gives you a feeling of a high-end resort! Will stay her again!"
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

Beautiful Home in paradise!

9.6 out of 10, Exceptional, (167)
"We so enjoyed our stay here. Both King beds were very comfortable, the garden is gorgeous and the house was large and comfortable. "
Beautiful Home in paradise!

Waterfall House - Private House Overlooking the Ocean!

9.8 out of 10, Exceptional, (24)
"This house is nestled inside the beginnings of the road to Hana. One of the most breathtaking places I’ve stayed in my life. Just beware, it is really hard to leave because it’s so beautiful!! The house itself is incredibly unique, there are little treasures everywhere that aren’t even pictured. "
Waterfall House - Private House Overlooking the Ocean!

Fabulous views! Exclusive pool, spa and private 1 acre yard.

10.0 out of 10, Exceptional, (134)
"We had a great stay! The property is beautiful and close to beaches, restaurants, and groceries. It was exactly what our family of four was looking for."
Fabulous views! Exclusive pool, spa and private 1 acre yard.

Hana Ocean Palms Bungalows

9.6 out of 10, Exceptional, (113)
"A really lovely property in Hana. Thank you for having us! "
Hana Ocean Palms Bungalows

Serene Eco Retreat: Ocean Views, Waterfalls, and Scenic Trails!

10.0 out of 10, Exceptional, (2)
"This place was amazing a great place to get away from everything and relax and enjoy what Maui has to offer! If you are the type who wants to get away from all of the hustle and bustle! This Place Is Heaven! William the caretaker of the property was so great. He was there to help us with anything we needed, he greeted us upon arrival and we got in rather late, showed us around and made us feel welcomed. I would definitely Love to come and stay at this Retreat again!"
Serene Eco Retreat: Ocean Views, Waterfalls, and Scenic Trails!

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

10.0 out of 10, Exceptional, (62)
"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."
The price is SAR 5,232
SAR 10,319 total
includes taxes & fees
13 Jun - 14 Jun
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

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

9.8 out of 10, Exceptional, (152)
"The experience couldn’t have been better! The house is lovely and was just what our family was looking for in being a home away from home in paradise. The house was full of useful amenities - kitchen is fully stocked; the laundry is great; and there is everything you need for the beach!The location is very close to town but far enough away to feel completely relaxed.Our family would absolutely stay here again!"
Breath taking ocean and volcano views! Pool,Close to beaches and everything else

IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

10.0 out of 10, Exceptional, (177)
"One week enjoying the Hana area"
The price is SAR 1,181
SAR 2,056 total
includes taxes & fees
15 Jun - 16 Jun
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

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

9.8 out of 10, Exceptional, (167)
"Fantastic location. We stayed here with family when we were in town for a wedding. Such a special place to wake up each morning and watch the ocean. The home was very spacious and comfortable for a large group. "
Breathtaking Oceanfront Location, Gorgeous Views, Stroll to Hamoa Beach, Hot Tub

Upcountry Single Level Private 3 Bedroom Home in Marvelous Kula!!!

10.0 out of 10, Exceptional, (1)
"Maddie and Jimmy could not have been friendlier or more thoughtful hosts. They welcomed us to their beautiful home with a bounty of food and treats, including fresh eggs from their flock of hens. They were also readily available for anything we might need.The location was perfect for our trip to an Upcountry family funeral, but Kula is also a great location for visiting Haleakala, Makawao, and the other local attractions. We spent most of our days at our relativeʻs house, but one morning...
Upcountry Single Level Private 3 Bedroom Home in Marvelous Kula!!!

Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach

9.8 out of 10, Exceptional, (86)
"Wonderful home with nice amenities."
Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach

Upcountry Short Term Rental Home with Ocean and Mt Views, Close to Makawao Town.

9.4 out of 10, Exceptional, (88)
"As local contracted workers in Hawaii, Mark is a gracious host and his place was completely accommodating for our needs."
Upcountry Short Term Rental Home with Ocean and Mt Views, Close to Makawao Town.

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

10.0 out of 10, Exceptional, (141)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Our fourth time staying here and it never disappoints. Lovely view, lovely home. Quiet neighborhood. Great location. We can't wait to come back."
Summer Deals Book now Island Retreat Spacious 3B 3B home.

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

9.2 out of 10, Wonderful, (138)
"We liked the flat very much. Clean, cosy, like described."
The price is SAR 996
SAR 2,271 total
includes taxes & fees
12 Jun - 13 Jun
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

Romantic Hana Hideaway, Big Ocean Views, Old Hawaii Charm

9.8 out of 10, Exceptional, (139)
"Nice place to stay."
The price is SAR 1,313
SAR 2,491 total
includes taxes & fees
3 Jul - 4 Jul
Romantic Hana Hideaway, Big Ocean Views, Old Hawaii Charm
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.
Save an average of 15% on thousands of hotels when you're signed in