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Compare 34 Vacation Homes in Kaupo with updated reviews, rates, and availability.

Fisher's Hana Bay Hale, Across from Hana Bay

9.4 out of 10, Exceptional, (358)
"Overall very nice, reasonably priced. Would recommend adding some board games since there’s no ping pong after 7pm. Door to lanai locks but sliders to house don’t. Cute neighborhood cat! "
Fisher's Hana Bay Hale, Across from Hana Bay

IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

10.0 out of 10, Exceptional, (172)
"Great quiet location. Listen to the ocean and the birds. "
The price is AED 1,285
AED 2,196 total
includes taxes & fees
13 Mar - 14 Mar
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

Beautiful Home in paradise!

9.6 out of 10, Exceptional, (160)
"Very spacious! 10 min short trip from Hana and 5 min to waianapanapa state park"
Beautiful Home in paradise!

Island Retreat Spacious 3B/3B Wailea Home Ocean View Private Pool & Hot Tub!

9.8 out of 10, Exceptional, (138)
"We had an amazing time at this vacation rental! Right from the start, we were blown away by how clean, spacious, and well-equipped the house was. It looked just like the photos and description on VRBO. The kitchen had everything we needed to whip up our meals, and the living areas were perfect for the whole family. The deck with the hot tub was a fantastic way to unwind after a long day at the beach, and the sunset views were just incredible. We even caught some fireworks from the Grand Wailea...
Island Retreat Spacious 3B/3B Wailea Home Ocean View Private Pool & Hot Tub!

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

9.8 out of 10, Exceptional, (80)
"Our family of five adults just finished a 10 day Stay here. Looks just like the pictures. The view is amazing!!!! The house is a great size for families with plenty of room to spread out and have your own space with tons of outdoor seating and areas. We enjoyed the pool and the hot tub every day and the beach is a pretty close drive. You can walk to the beach, however it is all downhill for a long way so unless you’re very fit, I wouldn’t recommend it, as you’d be going entirely uphill in the...
Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach

Waterfall House - Private House Overlooking the Ocean!

9.8 out of 10, Exceptional, (24)
"Pros: Incredible setting and the grounds are beautiful. Whale watching from the hot tub was probably the highlight of our trip. The pool gets the perfect amount of sun on the nice days. The whole property is very calm and relaxing. The people onsite are incredibly friendly and do not disturb the guests.Cons:The circle bed in the listing photos in incredibly uncomfortable. Getting in and out you or rolling or kneeling on marble to get on a mattress that has seen better decades. We would've slept...
Waterfall House - Private House Overlooking the Ocean!

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

10.0 out of 10, Exceptional, (215)
"I have stayed in many rental homes and this is by far the best equipped rental home I have ever stayed in. We love to cook and usually can’t find enough pots and pans and utensils and this house had them all.We also had the privilege of their neighbors having goats and baby goats and cows which we enjoyed seeing from the deck of the house The house was also close enough to major towns And easy to find I would definitely stay here again on our next trip to Maui "
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

4-bedroom mini-splits AC vacation home just 5 minutes drive to Wailea Beach

10.0 out of 10, Exceptional, (56)
"This was our first trip to Maui. Linda was very attentive and sent us multiple recommendations so that we could have an idea of things we wanted to do prior to our stay. Having access to the pool was very nice as well for the evenings we wanted to continue relaxing in the water without the beach. We highly recommend this property and would love to rent it again in the future!! "
4-bedroom mini-splits AC vacation home just 5 minutes drive to Wailea Beach

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

9.8 out of 10, Exceptional, (70)
"Home exceeded our expectations. Private beautiful backyard and clean home. Quick access to everywhere we needed to go and had chairs and towels for the beach. Highly recommend this property! "
PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING

3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

9.8 out of 10, Exceptional, (69)
"My family and my oldest daughter’s family stayed together for a long weekend. Close to everything and a wonderful home. "
The price is AED 2,204
AED 3,904 total
includes taxes & fees
30 Mar - 31 Mar
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

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

9.8 out of 10, Exceptional, (213)
"Clean, Comfortable & QuietBeautiful yard & patioComfortable bedsLocation is greatThere is not a negative thing to say about this place! This is our 2nd stay & we will definitely be back for another. This is a great place!"
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

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 2,534
AED 5,579 total
includes taxes & fees
1 Apr - 2 Apr
Hana Homestead by the Beach

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

9.4 out of 10, Exceptional, (24)
"Everything was great with one exception: the outside waste bins were full to overflowing. "
Hana Bay View 3 BR/2 BA house sleeps 6 comfortably with 2 patios.

Hana Ocean Palms Bungalows

9.6 out of 10, Exceptional, (110)
"We loved Albert’s place and the magic he has hidden in this quaint gem of a cottage. What a host! So many lovely surprises during our stay we had the privilege to discover in the area and on the property . Be sure to go to the local farmers market. Bring 2 bills. They are a special compliment here and considered lucky. I love plants and was able to spend some time learning all about the ginger, bananas, orchids, coconuts, avocados and what seemed like dozens of other amazing finds right there....
Hana Ocean Palms Bungalows

Cliff House - Stunning Private Home with Ocean View and Pool and Spa

9.6 out of 10, Exceptional, (18)
"This place is paradise!!! "
Cliff House - Stunning Private Home with Ocean View and Pool and Spa

Mahina Cottage, Mahina Cottage

9.8 out of 10, Exceptional, (10)
"WARNING - You will not want to leave. This place is an absolute gem of a find. Shems was very communicative and made check in/out a breeze. The kitchen is well stocked with coffee, spices, etc. they even left us a bottle of wine, banana bread and honey from their own bees!! Everything was clean and cute. The view from the balcony was incredible. If we ever make our way back to Maui, this will be the only place we stay. "
Mahina Cottage, Mahina Cottage

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

9.8 out of 10, Exceptional, (129)
"This a beautiful house with a stunning view. With the pool and jacuzzi there’s almost no reason to leave the house!!"
Fabulous views! Exclusive pool, spa and private 1 acre yard.

Luxury Upcountry Villa with breathtaking views

10.0 out of 10, Exceptional, (37)
"This place is great. The views are incredible. We had a great time here and would have loved to stay longer. Watching the sunset from the hot tub, cooling down in the pool afterwards, lying in bed watching the moon set in the mornings. The quiet and peacefulness of the upcountry. Memories we will never forget."
Luxury Upcountry Villa with breathtaking views

Dolphin Room at Maui Eco Retreat: Ocean Views & Private Waterfall!

9.6 out of 10, Exceptional, (5)
"A refreshing alternative to the glitzy sides of Maui, washed in rain showers and rainbows but close enough to good beaches and the slow pace of Paia and Haiku. The “personal waterfall” that’s advertised though is a real stretch. It’s down a very steep and slippery unmaintained trail with a proceed at your own risk sign. We turned back. "
Dolphin Room at Maui Eco Retreat: Ocean Views & Private Waterfall!

Fantastic Hana Bay Oceanfront Location! 5-Minute Walk to Hana town & beaches!

10.0 out of 10, Exceptional, (14)
"Clean, quiet, beautiful view, lots of lizards."
Fantastic Hana Bay Oceanfront Location! 5-Minute Walk to Hana town & beaches!
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

Wailea Ekolu - CoralTree Residence Collection

3.5 star property
8.8 out of 10, Excellent, (248)
"Very nice area ... lush and green. Beautiful beaches but quite a walk."
Wailea Ekolu - CoralTree Residence Collection

Fisher's Hana Bay Hale, Across from Hana Bay

9.4 out of 10, Exceptional, (358)
"Overall very nice, reasonably priced. Would recommend adding some board games since there’s no ping pong after 7pm. Door to lanai locks but sliders to house don’t. Cute neighborhood cat! "
Fisher's Hana Bay Hale, Across from Hana Bay

Oceanview Condo in Hana-Let the ocean lull you to sleep

9.0 out of 10, Wonderful, (77)
"Quiet and comfortable property in Hana at a good price point. We wish we had spent more time in Hana and could have enjoyed the property further."
The price is AED 735
AED 1,461 total
includes taxes & fees
9 Mar - 10 Mar
Oceanview Condo in Hana-Let the ocean lull you to sleep
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.