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.

  • 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


    180 USD - 300 USD


    1,260 USD - 2,100 USD


    5,040 USD - 8,400 USD


  • 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 Experience a delightful part of “old Hawaii” with all modern conveniences by staying at the Menehune Cottage i...

    2 Bedrooms, 1 Bathrooms, Sleeps 4


    195 USD - 295 USD


    2,065 USD - 2,065 USD


  • Paia Ko - beautiful ocean view home with central air and other fine amenities

    Paia Ko, Permit STPH 2015/0002, is a quiet, lovely, 3 bedroom 2 and a half bath home with beautiful ocean views and central air conditioning that backs up to a sugar cane field. With the benefit of a sidewalk It's about a fifteen walk to downtown ...

    3 Bedrooms, 2 Bathrooms, Sleeps 6


    305 USD - 345 USD


    2,415 USD - 2,415 USD


  • 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


  • Short walk to Baldwin/Baby Beach, remodeled, fabulous patio - Permitted

    Permit: BBWK2009-0003. TA-020-791-2960-01. Kahale Makani is just around the corner from Baby Beach and Baldwin Beach. Is it walking distance? Absolutely! And the best thing is that it will only take a couple of minutes. Located off the ocea...

    3 Bedrooms, 3 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