North Shore and Upcountry Homes & Cottages

The island’s northeastern coast and its surrounding communities are referred to as Maui’s North Shore. The charming village of Paia is Maui’s primary North Shore town. Heading inland from Paia, there are a number of small residential towns scattered along the slopes of Mount Haleakala. This area, called Upcountry Maui, is known for its cooler temperatures, expansive ranch land, and spectacular panoramic views of the island’s coastline. Maui north shore vacation rentals or homes in Upcountry Maui can provide a relaxed and unique island experience for visitors who enjoy being outside the busier, more traditional “tourist areas.”

Menehune House

Menehune House in Paia is located within easy walking distance to Mama’s beach (the Kuau Channel) for surfing and windsurfing access. This charming “beach house” style home offers three bedrooms (all with queen size...See More →

Rates from: $425  

Guests: Up to 6

Bedrooms: Up to 3

Friendly Beach Vacation Suite

Our Friendly Beach Vacation Suite is located on what some people call the best watersports vacation beach in the world...others call it the best "chill spot" on Maui. Situated between Kanaha and Baldwin Beach...See More →

Rates from: $325  

Guests: Up to 4

Bedrooms: Up to 1

Milo Bungalow and Palm Cottage

Four-bedroom Milo Bungalow and two-bedroom Palm Cottage are Hawaiian themed and are located on the same ocean front lot in the heart of Paia, but are surprisingly private. One or both are perfect for...See More →

Rates from: $325  

Guests: Up to 11

Bedrooms: Up to 6

Maui by the Sea

Maui by the Sea is a beautiful vacation rental—an ideal oceanview cottage located on an oceanfront property between Paia and Hookipa, on Maui's scenic and exciting North Shore. Our two-story plantation-style cottage has gorgeous...See More →

Rates from: $275  

Guests: Up to 2

Bedrooms: Up to 1

Huelo Point Lookout

Especially popular with honeymoon couples, Huelo Point Lookout is a unique hideaway with gorgeous views sweeping along Maui’s north shore cliffs to Hana, then back inland right up to the 10,000-foot summit of Mt...See More →

Rates from: $250  

Guests: Up to 8 + kids

Bedrooms: Up to 4

Hale Mauka Makai

This beautiful 3 bedroom, 3 bath Haiku home conquers your heart and soul the moment you step in, with its simple elegance and unbelievable feeling. Set on over 4 acres of estate-like gardens, Hale...See More →

Rates from: $600  

Guests: Up to 9

Bedrooms: Up to 3

Ho’okipa Bayview Cottage

Ho'okipa Bayview Cottage in Haiku has a spectacular ocean/sunset view. Luxurious king bed, deep soaking tub for 2. Spacious walk-in luxury shower plus 2 side-by-side outdoor showers off the private sundeck overlooking a peaceful...See More →

Rates from: $289  

Guests: Up to 2

Bedrooms: Up to 1

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