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Top Holiday Rentals in Kaupo

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

9.6 out of 10, Exceptional, (394)
"The property was excellent, highly recommend. "
The price is £269
includes taxes & fees
9 Sept - 10 Sept
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

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

9.2 out of 10, Wonderful, (104)
"An idyllic setting where we could see the bay, hear the waves, with a short walk to the beach (black rocky sands). Neighbors a bit loud, but still one of the best spots in Hāna. Easy drive to the 7 sacred pools. Good food trucks nearby. "
The price is £350
includes taxes & fees
26 Aug - 27 Aug
Oceanview Condo in Hana-Let the ocean lull you to sleep

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

10.0 out of 10, Exceptional, (67)
"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 £2,283
includes taxes & fees
10 Sept - 11 Sept
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Secluded cottage on Tropical flower farm

9.6 out of 10, Exceptional, (265)
"We had a good time, thanks for sharing your place. "
The price is £421
includes taxes & fees
1 Sept - 2 Sept
Secluded cottage on Tropical flower farm

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

10.0 out of 10, Exceptional, (80)
"After eight trips to Hawaii, this is the first place where I really felt I was in paradise. "
The price is £409
includes taxes & fees
29 Aug - 30 Aug
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!

9.6 out of 10, Exceptional, (20)
"Excellent all around property"
Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!

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

10.0 out of 10, Exceptional, (228)
"Lovely property and very enjoyable place to stay. Great location."
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

Fisher's Hana Bay Hale, Across from Hana Bay

9.4 out of 10, Exceptional, (396)
"Lovely getaway after our long on the road to Hana drive. Provided everything we needed with kitchen, 1bedroom and nice full-size bed tucked in the corner off the TV room. Loved the woody walls, plenty of ceiling fans and distant view of the bay. Check this place out folks!"
The price is £299
includes taxes & fees
8 Sept - 9 Sept
Fisher's Hana Bay Hale, Across from Hana Bay

Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views

10.0 out of 10, Exceptional, (177)
"Great place !!"
The price is £752
includes taxes & fees
26 Aug - 27 Aug
Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views

Oceanfront #5 at Hana Kai Maui - 2 BR/2 BA Upper Floor Corner 100ʻ from Water!

10.0 out of 10, Exceptional, (68)
"Amazing view and cozy ! One night stay but very worth it. "
The price is £558
includes taxes & fees
28 Aug - 29 Aug
Oceanfront #5 at Hana Kai Maui - 2 BR/2 BA Upper Floor Corner 100ʻ from Water!

Exceptional Upcountry Villa with breathtaking views

10.0 out of 10, Exceptional, (44)
"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!"
Exceptional Upcountry Villa with breathtaking views

Couples & Honeymooners. Privacy & Romance! 7 Sacred Pools

9.8 out of 10, Exceptional, (250)
"A little work to get there but the setting and activities on this side of the island are fabulous and worth several days. Eating option are limited so need to pack in some groceries. Beautiful, relaxing setting!"
Couples & Honeymooners. Privacy & Romance! 7 Sacred Pools

Tropical stays where comfort meets the course

9.4 out of 10, Exceptional, (16)
"Great stay!"
Tropical stays where comfort meets the course

Wailea Ekolu - CoralTree Residence Collection

3.5 star property
8.8 out of 10, Excellent, (261)
"It’s a great place to Stay for the family vacation."
The price is £581
includes taxes & fees
26 Aug - 27 Aug
Wailea Ekolu - CoralTree Residence Collection

Beautiful Condo, Private Lanai, Near Wailea Beaches

9.6 out of 10, Exceptional, (165)
"We had a great vacation. If we come to Maui again we would choose to stay again."
Beautiful Condo, Private Lanai, Near Wailea Beaches

IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

10.0 out of 10, Exceptional, (180)
"Located a few miles beyond Hana, this is a well-equipped and very comfortable rental. "
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

Oceanview #104 at Hana Kai Maui - 1 Bedroom, Easy Access (no steps), Great View!

9.6 out of 10, Exceptional, (73)
"Our second trip ! We enjoy every time ! "
The price is £317
includes taxes & fees
26 Aug - 27 Aug
Oceanview #104 at Hana Kai Maui - 1 Bedroom, Easy Access (no steps), Great View!

Hawaiian Cottage and Personal Paradise /BBKM 2013/0004

10.0 out of 10, Exceptional, (194)
"Could not have been better. Cottage is a little jewel. Carrie, the host,is an amazing, kind and helpful person, Highly recommend staying at the cottage."
Hawaiian Cottage and Personal Paradise /BBKM 2013/0004

Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

9.6 out of 10, Exceptional, (71)
"Best Suite & view was excellent!!"
The price is £343
includes taxes & fees
28 Aug - 29 Aug
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

Beautiful Hana, Near Waianapanapa State Park. STR 216/0003 TA186-656-9728-01

9.8 out of 10, Exceptional, (190)
"We spent two nights at the property. We’re so glad we had extra time in Hana. We really enjoyed the covered porch with the nice breeze. The kitchen had everything we needed, and we appreciated the extra touches like having a jar of local coffee and the coffee presses. I was pleasantly surprised by the water pressure and the wonderful hot water from the solar system! And the outside shower was fantastic! If we’re ever lucky enough to come back to Hana, we would definitely stay here again. "
Beautiful Hana, Near Waianapanapa State Park. STR 216/0003 TA186-656-9728-01
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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Top Kaupo Hotel Reviews

Frequently asked questions

Are there holiday rentals in Kaupo?

Yes, there are holiday rentals close to the most popular sights in Kaupo, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Kaupo has to offer?

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002 : This holiday home rental outside of Kaupo is located in a rural location, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind.

What’s there to see and do in Kaupo?

Explore the area and family-friendly sights such as Waikamoi Preserve, or get out into nature at a spot like Haleakala National Park. Bamboo Forest and Wailua Falls are a couple of places you'll find in the wider area.

What’s a holiday rental in Kaupo like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kaupo. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a family trip.