Best price vacation rentals in Upcountry, Maui, HI, USA • 48 Listings
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Upcountry, Maui, HI, USA Vacation Rentals | 

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5.0 (35)
North Shore Lookout Maui - Pele Suite - Upcountry - Makawao - Maui! B&B
Up to 3 guests
Vrbo$315
Airbnb$325
Average Nightly Rate
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5.0 (27)
North Shore Lookout Maui! Hoku Suite -upcountry -Makawao -Maui B&B
Up to 2 guests
Airbnb$342
Vrbo$350
Average Nightly Rate
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5.0 (108)
Upcountry Kula - Private House On The Slopes Of Haleakala - Multi-Island View
Up to 4 guests
Vrbo$299
Airbnb$313
Average Nightly Rate
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5.0 (71)
Luxury Upcountry retreat with breathtaking views!
Up to 2 guests
Vrbo$395
Airbnb$395
Average Nightly Rate
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5.0 (191)
Ocean View Cabin located on Organic Coffee Farm with Hiking Trails
Up to 4 guests
Airbnb$320
Vrbo$326
Average Nightly Rate
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5.0 (705)
2BR Suite with Hot Tub & Fruit Trees, on the Way to Haleakala National Park!
Up to 4 guests
Airbnb$139
Vrbo$143
Average Nightly Rate
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5.0 (114)
PERMITTED Charming LOG HOUSE in REAL Upcountry Maui. Magical and Peaceful!
Up to 10 guests
Airbnb$850
Vrbo$850
Average Nightly Rate

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5.0 (48)
Sensational View - Central Location - Clean and Cozy
Up to 2 guests
Airbnb$199
Vrbo$212
Average Nightly Rate
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5.0 (78)
Beautiful Cozy Cottage 15 Minute Drive to Beaches
Up to 4 guests
Airbnb$206
Vrbo$220
Average Nightly Rate

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5.0 (37)
Nestled on the Slopes of Haleakala with a View from Coast to Coast - Permitted
Up to 6 guests
Airbnb$595
Vrbo$595
Average Nightly Rate
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4.9 (236)
Private Home with Pool & Fruit Trees, on the Way to Haleakala National Park!
Up to 7 guests
Airbnb$289
Vrbo$298
Average Nightly Rate
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4.9 (127)
Pookela Paradise 2-Panoramic Ocean Views, Big Yard, Secluded but close to Town.
Up to 8 guests
Vrbo$391
Airbnb$443
Average Nightly Rate
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5.0 (16)
Historic Maui House, 7 Unit Estate, Pool, Central Maui Location
Up to 16 guests
Vrbo$1,431
Average Nightly Rate
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5.0 (29)
Hike on Scenic Trails at a Luxury House on Seven Acres
Up to 4 guests
Airbnb$975
Average Nightly Rate
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5.0 (131)
Malu Manu
Up to 2 guests
Airbnb$375
Average Nightly Rate
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5.0 (20)
Romantic garden cottage with hottub
Up to 4 guests
Airbnb$325
Average Nightly Rate
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5.0 (261)
HALEKALANI - Paradise in Upcountry
Up to 4 guests
Airbnb$266
Average Nightly Rate
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5.0 (65)
Maui Star Dome - Includes Skylight Loft Bedroom
Up to 2 guests
Airbnb$325
Average Nightly Rate
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5.0 (28)
North Shore Lookout Maui - PANIOLO SUITE -Maui B&B
Up to 4 guests
Airbnb$342
Average Nightly Rate
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5.0 (71)
sweet country cottage on 2 acres; palm trees birds
Up to 2 guests
Airbnb$250
Average Nightly Rate
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5.0 (24)
House of light
Up to 4 guests
Airbnb$350
Average Nightly Rate
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5.0 (185)
Maliko Retreat
Up to 4 guests
Airbnb$434
Average Nightly Rate
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5.0 (40)
beautiful 3 bedroom 2 1/2 bath upscale upcountry
Up to 6 guests
Airbnb$450
Average Nightly Rate
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5.0 (22)
Maui Escape
Up to 3 guests
Vrbo$295
Average Nightly Rate
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5.0 (109)
Oceanview Cottage away from heat! w/ County Permit
Up to 4 guests
Airbnb$310
Average Nightly Rate
  1. United States
  2. Hawaii
  3. Maui
  4. Upcountry Vacation Rental Price Comparison

More price comparison of vacation rental locations

  1. Central Maui
  2. East Maui
  3. North Shore
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  5. West Maui

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