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. permitted, air conditioned cottage, walking distance to Paia.

    Permitted vacation rental, STPH2013/0004 Nestled on Baldwin Avenue, our plantation style one bedroom cottage provides convenient and comfortable accommodations for up to 3 people (1 king bed and 1 double sofa bed) with the amenities of Historic...

    1 Bedrooms, 1 Bathrooms, Sleeps 2


    180 USD - 180 USD


    1,175 USD - 1,175 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. ** 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


  • 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


  • Sprecks Plumeria w/Large Lanai

    Permit Number: BBWK 2014/0002. TAT W43140178-01, Located on the north shore of Maui and half way between the town center of Paia and the airport. Ten minutes in either direction. Just off the Hana Hwy. Great location for windsurfers, kiters, surfe...

    0 Bedrooms, 1 Bathrooms, Sleeps 2


  • Beautiful Historic Oceanfront Compound - Paia Paradise Beach House

    4 bedroom 3 bath - Vacation License #STPH 20130015 Experience the beauty of a Maui vacation with the comforts of a family home. Paia Paradise Beach House is an old plantation style home with modern updates that take you back to the ambiance of ano...

    4 Bedrooms, 3 Bathrooms, Sleeps 9


  • 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 4 bedroom, two bathroom, oceanfront cottage, sleeps 7, one rental group at a time. Relax in this charming 2 story house or under the palm trees. Enjoy the surf or nearby swimming beach. M...

    4 Bedrooms, 2 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 Cottage Steps from the Beach!

    We would love for you to stay at our Cottage and experience the charming Historic town of Paia while having direct access to the private stunning Baldwin Beach within a few steps of our Cottage. Paia sits at the gateway to the road to Hana. Wit...

    0 Bedrooms, 1 Bathrooms, Sleeps 3