Paia Vacation Rentals

Paia is a historic plantation town on Maui’s north shore. Here you will find studio rentals, beach bungalows, romantic cottages and homes by the sea. Paia is the ideal vacation destination for those who want to be away from the typical touristy spots and still be in a lively place, where there is plenty to see and do. Paia is known as the "World Capital of Windsurfing" because of nearby Hookipa Beach, where the windsurfing conditions are excellent. Other nearby attractions are Haleakala National Park and the Road to Hana. Browse through this selection of Paia vacation rentals below and find the one that suits you best.

  • Charming Hawaiian style cottage, walk to beach & Mama's, private yard

    The Menehune Cottage & House are in a perfect location for an ocean-lover's holiday! Permitted: STPH2013/0010 - TAT/GET: WO1738206-02. ** Once the reservation is accepted, guests will receive our rental agreement to review, fill out and sign. **...

    2 Bedrooms, 1 Bathrooms, Sleeps 4


    195 USD - 295 USD


    2,065 USD - 2,065 USD


  • Large Studio In A Tropical Sanctuary Just A Short Walk To Paia Town & Beach

    We have 4 air-conditioned studios, and a 4 bedroom house on our property. This add features our 'Large Studio' it has a king size bed in the main room and a full size memory foam sofa sleeper in an adjacent sun room. Sleeps up to 3. There is a f...

    0 Bedrooms, 1 Bathrooms, Sleeps 3


    230 USD - 375 USD


    1,610 USD - 2,625 USD


    6,440 USD - 8,400 USD


  • Paia Luxury Beachfront Villa, 3 Bdr/2 Bath, Steps to White Sand Beach!

    Introducing a beachfront Maui vacation without the crowds! Permit # STRH 2013/0005 The Beachcomber is located in the heart of the hip beach town of Paia. You won’t find any skyscrapers, big hotels, or condo complexes in this historic plantation...

    3 Bedrooms, 2 Bathrooms, Sleeps 6


  • Maui Winds II Permit # STPHT2013/0019 - Charming home on Maui's north shore.

    Maui Winds II - permit # STPHT2013/0019 is the perfect for a romantic couple or family and friends. This breeze and charming home invites rest and relaxation and offers exciting activities for top notch athletes ready to windsurf, surf or bike Mau...

    2 Bedrooms, 1 Bathrooms, Sleeps 6


  • Maui Plantation Beach Home, Spreckelsville, Paia

    Maui Plantation Beach Home, Spreckelsville, Paia is only a short walk (3min/300 steps) to two of Maui's most beautiful and secluded beaches. Baby Beach is Maui's best swimming beach and voted second best beach on Maui! It's not just a home, it's ...

    4 Bedrooms, 3 Bathrooms, Sleeps 8


  • Beach Front Condo - Maui North Shore GET/TAT - W-01679382-01

    One of the rare BEACHFRONT Maui North Shore vacation rentals. WINDSURF, KITESURF, STAND UP PADDLE (SUP), and SURF from the yard! Hale Surf (say hah-lay surf, Hawaiian for Surf House) is as close to the ocean as it gets: just steps away from Sugar...

    3 Bedrooms, 4 Bathrooms, Sleeps 7


  • Maui North Shore Oceanfront Cottage

    Maui Country STPH permit # 20130018 GE/TAT 165-226-9056-01 2 bedroom oceanfront cottage, sleeps 4, one rental group at a time. Relax in this charming bungalow or under the palm trees. Enjoy the surf or the nearby swimming beach or watch the t...

    2 Bedrooms, 1 Bathrooms, Sleeps 4