Vacation rentals in Kaupo

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Top-rated vacation rentals in Kaupo

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite

Guesthouse in Kula

4.98 out of 5 average rating, 161 reviews

Upcountry Alpaca, Llama, and Rabbit working farm

Experience Maui's first working fiber farm, home to Alpacas, Llamas, and Angora rabbits. Sitting at 3300 ft above sea level, Cottontail Farm enjoys perfect weather days and crisp, cool nights. The cooler temperatures are perfect for our wool producing animals that graze just outside your cottage in the back yard. Our alpacas and llamas are quiet observers but also provide plenty of entertainment of their own. Our group of Angora rabbits can be seen out the window hopping around their enclosures.

Nov. 12 – 19

$471 CAD per night
Guest favourite

Cabin in Maui

4.98 out of 5 average rating, 167 reviews

★Rainbow Lookout - PRIVATE HOT TUB+ACCESS TO POOL

This Stunning North Shore Maui hideaway is surrounded with lush fruit and flower gardens, coconut palms, banana trees, and has easy access to all there is to do on this magnificent island. Stargaze … soak in your own private hot tub with a chilled glass of wine and enjoy a once-in-a-lifetime experience. The 'real' Maui:)! ★Jump Start to The to the Road to Hana! ✔ ★New Cold Central AC ✔ ★Cliff Walk ✔ ★Ocean View✔ ★Private Hot Tub ✔ ★44 ft Swimming Pool ★King Bed ✔ ★Sunrise View✔ ★Star Gazing✔

Mar. 5 – 12

$1,237 CAD per night
Guest favourite

Cottage in Hana

4.95 out of 5 average rating, 101 reviews

Solar Cottage With Privacy & Panoramic Ocean Views

Entabeni Cottage sits above the Road to Hana overlooking the Pacific Ocean on the north shore of Maui, Hawaii. Entabeni Cottage is a fully-equipped, 830 square foot home, powered by the sun and beautifully situated on a gorgeous 6.25 acre tropical flower farm. Enjoy ocean views from your bed, kitchen, lanai (covered deck), & private yard. The Kristiansen's offer guests fresh eggs and vegetables from the garden when ready for harvest. License & Permit: BBHA 2013/0006 and SUP2 2012/0011

Aug. 9 – 16

$519 CAD per night

Popular amenities for Kaupo vacation rentals

Other great vacation rentals in Kaupo

Guest favourite

Guest suite in Hana

4.83 out of 5 average rating, 151 reviews

Whale Watch Suite, Hana, Maui, HI

Apr. 5 – 12

$613 CAD per night
Guest favourite

Cottage in Kula

4.96 out of 5 average rating, 327 reviews

HALEKALANI - Paradise in Upcountry

Oct. 30 – Nov. 6

$484 CAD per night
Superhost

Farm stay in Hana

4.9 out of 5 average rating, 134 reviews

Hana Nautilus- Ocean view 3 bed 2 bath family home

Dec. 4 – 11

$1,230 CAD per night
Guest favourite

Cottage in Hana

4.91 out of 5 average rating, 244 reviews

STHA Permit 2016/0003 TA 186-656-9728-01

Dec. 13 – 20

$516 CAD per night
Superhost

Home in Hana

4.8 out of 5 average rating, 344 reviews

STHA 2017/0002 TA-061-740-4416-01 Hana Maui Hawaii

Feb. 15 – 22

$346 CAD per night
Superhost

Condo in Kihei

4.84 out of 5 average rating, 261 reviews

★Couples Paradise w/ Lanai★ 3 min. walk to beach!

Jan. 1 – 8

$268 CAD per night
Guest favourite

Cottage in Kula

4.95 out of 5 average rating, 276 reviews

Oceanview Cottage away from heat! w/ County Permit

Jul. 29 – Aug. 5

$634 CAD per night
Guest favourite

Cottage in Haiku-Pauwela

4.95 out of 5 average rating, 350 reviews

Explore Waterfalls and Beaches from a Tropical Haiku Cottage

Feb. 2 – 9

$820 CAD per night
Superhost

Apartment in Kihei

4.83 out of 5 average rating, 467 reviews

Hawaiian Paradise Escape Across Street from Beach

Mar. 24 – 31

$240 CAD per night
Superhost

Apartment in Hana

4.78 out of 5 average rating, 504 reviews

Stay in Hana #1

Dec. 5 – 12

$357 CAD per night
Guest favourite

Home in Hana

4.93 out of 5 average rating, 176 reviews

Hana Homestead by the Beach

Apr. 13 – 20

$1,009 CAD per night
Guest favourite

Cottage in Makawao

4.93 out of 5 average rating, 570 reviews

Adorable Garden Gingerbread House

Apr. 11 – 18

$539 CAD per night

Destinations to explore

  1. Airbnb
  2. United States
  3. Hawaii
  4. Maui County
  5. Kaupo