Holiday rentals in Kaupo
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Kaupo
Guests agree: these stays are highly rated for location, cleanliness and more.
Guest house in Kula
4.98 out of 5 average rating, 161 reviewsUpcountry 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.
12–19 Nov
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✔
5–12 Mar
Cottage in Hana
4.95 out of 5 average rating, 101 reviewsSolar 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
9–16 Aug
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Kaupo holiday rentals
Other great holiday rentals in Kaupo
Guest suite in Hana
4.83 out of 5 average rating, 151 reviewsWhale Watch Suite, Hana, Maui, HI
5–12 Apr
Cottage in Kula
4.96 out of 5 average rating, 327 reviewsHALEKALANI - Paradise in Upcountry
30 Oct – 6 Nov
Farm stay in Hana
4.9 out of 5 average rating, 134 reviewsHana Nautilus- Ocean view 3 bed 2 bath family home
4–11 Dec
Cottage in Hana
4.91 out of 5 average rating, 244 reviewsSTHA Permit 2016/0003 TA 186-656-9728-01
13–20 Dec
Home in Hana
4.8 out of 5 average rating, 344 reviewsSTHA 2017/0002 TA-061-740-4416-01 Hana Maui Hawaii
15–22 Feb
Apartment in Kihei
4.84 out of 5 average rating, 261 reviews★Couples Paradise w/ Lanai★ 3 min. walk to beach!
1–8 Jan
Cottage in Kula
4.95 out of 5 average rating, 277 reviewsOceanview Cottage away from heat! w/ County Permit
29 Jul – 5 Aug
Cottage in Haiku-Pauwela
4.95 out of 5 average rating, 350 reviewsExplore Waterfalls and Beaches from a Tropical Haiku Cottage
2–9 Feb
Flat in Kihei
4.83 out of 5 average rating, 467 reviewsHawaiian Paradise Escape Across Street from Beach
24–31 Mar
Flat in Hana
4.78 out of 5 average rating, 505 reviewsStay in Hana #1
5–12 Dec
Home in Hana
4.93 out of 5 average rating, 176 reviewsHana Homestead by the Beach
13–20 Apr
Cottage in Makawao
4.93 out of 5 average rating, 570 reviewsAdorable Garden Gingerbread House
11–18 Apr
Destinations to explore
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom