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Compare 36 Vacation Homes in Kaupo with updated reviews, rates, and availability.

Fisher's Hana Bay Hale, Across from Hana Bay
Interior
Fisher's Hana Bay Hale, Across from Hana Bay
9.6 out of 10, Exceptional, (331)
"I come to Kihei every year, It had been a long time since I stayed at Hana and I was looking forward to it. The house is very clean and spacious with a ping pong table on the lanai, it was a great place to spend a relaxing time. I would like to stay here again next time I visit Hana."
The price is AED 716
AED 1,465 total
includes taxes & fees
17 Nov 2024 - 18 Nov 2024
Fisher's Hana Bay Hale, Across from Hana Bay
STHA-2017/0002 Across from Hana Bay
STHA-2017/0002 Across from Hana Bay
9.6 out of 10, Exceptional, (325)
"Property was as described and well kept. It had everything we needed including a couple of fans to help fight the heat/humidity. Very nice place to stay if you want to break up the road to Hana or spend more time to see more sights. Thank you for sharing your house. "
The price is AED 639
AED 1,308 total
includes taxes & fees
2 Dec 2024 - 3 Dec 2024
STHA-2017/0002 Across from Hana Bay
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b
Ocean-facing lanai with electric bbq.
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b
9.2 out of 10, Wonderful, (134)
"Is right next to road so a bit noisy but sitting on back deck was lovely"
The price is AED 1,084
AED 2,174 total
includes taxes & fees
5 Nov 2024 - 6 Nov 2024
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b
Private & Fabulous views! Exclusive pool, spa and 1 acre yard
Panoramic view from the deck. Master bedroom view is even better !
Private & Fabulous views! Exclusive pool, spa and 1 acre yard
10.0 out of 10, Exceptional, (122)
"This is our third time staying in this house. Needless to say, we love it. Nothing beats sitting out on the lanai in the morning with coffee or watching Maui's fantastic sunsets. The house is well equipped and very comfortable. "
Private & Fabulous views! Exclusive pool, spa and 1 acre yard
Beautiful Home in paradise!
Dinning room
Beautiful Home in paradise!
9.6 out of 10, Exceptional, (156)
"Beautiful view, great front deck for breakfast! Appreciated the Kona coffee provided. Could use a few more mugs as we are all coffee drinkers! Nice to have beach towels, chairs and boogie boards. The master bath was roomy and beautiful. Price was very reasonable. Thank you for the wonderful stay "
Beautiful Home in paradise!
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
Welcome to Hale Noa
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
9.8 out of 10, Exceptional, (204)
"Such a beautiful piece of heaven on earth. So quiet and private. A wonderful place to unwind and e joy the beauty of Hana. "
The price is AED 1,194
AED 2,439 total
includes taxes & fees
5 Nov 2024 - 6 Nov 2024
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
Exterior
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 4,830 total
includes taxes & fees
5 Nov 2024 - 6 Nov 2024
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
Hana Ocean Palms Bungalows
Exterior
Hana Ocean Palms Bungalows
9.6 out of 10, Exceptional, (105)
"The Ocean Palms Bungalow is the perfect vacation home on the road to Hana. It is set back and hidden from the road and is surrounded by beautiful trees and a lush garden. I stayed at a similar cottage years ago but that home was sold and taken off the rental market. I have been searching for another like it for years but nothing has ever compared until now. The house is not a sleek, modern place with all new matchy- matchy furniture. But that is exactly what makes this place so special. It...
Hana Ocean Palms Bungalows
Fantastic Hana Bay Oceanfront Location! 5-Minute Walk to Hana town & beaches!
Relax in the swinging chairs on the covered deck overlooking Hana Bay.
Fantastic Hana Bay Oceanfront Location! 5-Minute Walk to Hana town & beaches!
10.0 out of 10, Exceptional, (10)
"We were beyond pleased with our stay. The home had everything we needed, and the views were magnificent. The short stroll down to the black sand beach was absolutely gorgeous. Loved it!"
Fantastic Hana Bay Oceanfront Location! 5-Minute Walk to Hana town & beaches!
Beautiful house in the Upscale Maui Meadows neighborhood
Front of the house with private parking
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
Luxury Upcountry Villa with breathtaking views
Pool
Luxury Upcountry Villa with breathtaking views
10.0 out of 10, Exceptional, (36)
"My friends/ contractor were taking a week long break from working and loved this place. Beautiful environment, clean, full amenities. Owner was super communicative. Great to get upcountry vibe"
Luxury Upcountry Villa with breathtaking views
Hana Bay View 3 BR/2 BA house sleeps 6 comfortably with 2 patios.
Hana Bay View Home
Hana Bay View 3 BR/2 BA house sleeps 6 comfortably with 2 patios.
9.2 out of 10, Wonderful, (21)
"I was not aware that the third bedroom did not have air conditioning. That is the one thing they could do to make this property perfect!"
Hana Bay View 3 BR/2 BA house sleeps 6 comfortably with 2 patios.
Upcountry Short Term Rental Home with Ocean and Mt Views, Close to Makawao Town.
Cozy and sheltered covered deck with dinette seating for four.
Upcountry Short Term Rental Home with Ocean and Mt Views, Close to Makawao Town.
9.4 out of 10, Exceptional, (84)
"Great place to stay. Would recommend anyone to stay here amongst the locals."
Upcountry Short Term Rental Home with Ocean and Mt Views, Close to Makawao Town.
Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach
Large crystal clear deep swimming pool and hot tub
Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach
9.8 out of 10, Exceptional, (75)
"Everything about this place is as depicted. I would highly recommend. Wish we could have stayed longer, the view is amazing!"
Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'
Exterior
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'
10.0 out of 10, Exceptional, (166)
"The owners were wonderful, and the house was perfect for our family of five. Just what we were looking for… No crowds, beautiful scenery, and a ton of family time!"
The price is AED 1,286
AED 2,184 total
includes taxes & fees
30 Nov 2024 - 1 Dec 2024
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'
Newly remodeled 4 BD Heated Pool very quiet and private home in Wailea area
new 4 bedrooms for the whole family.
Newly remodeled 4 BD Heated Pool very quiet and private home in Wailea area
10.0 out of 10, Exceptional, (52)
"This lovely home offered everything you could want- swimming pool, billiards, games to entertain any family. Everything was immaculate, a beautiful ocean view, peaceful surroundings yet just a short drive to restaurants and the beach. We hope to stay with you again!"
Newly remodeled 4 BD Heated Pool very quiet and private home in Wailea area
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, (208)
"Felt like home, comfortable and peaceful!"
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING
Private Home Oasis, 3 Bedroom, Fully Remodeled, Ocean Views
PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING
9.8 out of 10, Exceptional, (67)
"We would stay in this home again, 10/10- the only downside is we enjoyed being in the house so much we were not motivated to explore the island! The pool is lovely- a nice sized pool to enjoy as a family of four. I spent most of my time on the back deck, enjoying the view of the pool with the ocean in the distance. The landscaping is top-notCh and there are a variety of curious birds and little lizards to watch. The bedrooms are spacious and comfortable, the kitchen is well-appointed. We had a...
PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING
Up Country spacious Newly remodeled kitchen close to beach, airport, UpCountry
Exterior
Up Country spacious Newly remodeled kitchen close to beach, airport, UpCountry
9.6 out of 10, Exceptional, (30)
"Few of my sons teammates grouped together for a recent baseball tournament! House was perfect! Close to the field. Saved us by being able to make breakfast everyday!"
Up Country spacious Newly remodeled kitchen close to beach, airport, UpCountry
Hana Homestead by the Beach
Aerial View
Hana Homestead by the Beach
9.8 out of 10, Exceptional, (132)
"The view from this house is absolutely amazing!! It overlooks Hana bay and the lighthouse. You can literally sit in the hot tub on the front porch and watch the sunset over the bay!"
The price is AED 3,489
AED 6,816 total
includes taxes & fees
8 Nov 2024 - 9 Nov 2024
Hana Homestead by the Beach
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 Kaupo

STHA-2017/0002 Across from Hana Bay
STHA-2017/0002 Across from Hana Bay
9.6 out of 10, Exceptional, (325)
"Property was as described and well kept. It had everything we needed including a couple of fans to help fight the heat/humidity. Very nice place to stay if you want to break up the road to Hana or spend more time to see more sights. Thank you for sharing your house. "
The price is AED 639
AED 1,308 total
includes taxes & fees
2 Dec 2024 - 3 Dec 2024
STHA-2017/0002 Across from Hana Bay
Fisher's Hana Bay Hale, Across from Hana Bay
Interior
Fisher's Hana Bay Hale, Across from Hana Bay
9.6 out of 10, Exceptional, (331)
"I come to Kihei every year, It had been a long time since I stayed at Hana and I was looking forward to it. The house is very clean and spacious with a ping pong table on the lanai, it was a great place to spend a relaxing time. I would like to stay here again next time I visit Hana."
The price is AED 716
AED 1,465 total
includes taxes & fees
17 Nov 2024 - 18 Nov 2024
Fisher's Hana Bay Hale, Across from Hana Bay
Wailea Ekolu - CoralTree Residence Collection
Exterior
Wailea Ekolu - CoralTree Residence Collection
3.5 star property
8.8 out of 10, Excellent, (242)
"Most excellent!!!"
Wailea Ekolu - CoralTree Residence Collection
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.