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.

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  • Ocean View home with central a/c - Walk To Downtown Paia and Beaches

    Permit STPH 2015/0002 GET: 146669772802 TAT: 14666977280
    Paia Ko is a quiet, lovely, 3 bedroom 2 and a half bath home with beautiful ocean views and central air conditioning that backs up to an old sugar cane field. With the benefit of a ...

    • 3 bedroom
    • 3 bathroom
    • Sleeps 6
    Hawaii> Paia
    157  reviews
    from $299 
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  • Romantic Beach Villa, Private Pool & Courtyard - 3 min. Walk to Baby Beach

    Gorgeous and elegant 3 Bedroom/3 Bath Beach Home, a few steps from famous Baby Beach is waiting for your arrival. Perfect for couples. This beautiful and renovated Beach Home is your ticket to a perfect vacation. Nestled in a quiet upscale ...

    • 3 bedroom
    • 3 bathroom
    • Sleeps 6
    Hawaii> Paia
    65  reviews
    from $1,616 
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  • IDEALLY LOCATED, FABULOUS "HALE NANEA" Beach House- AC

    HI Tax ID-W01462890-02

    31 Kaiholo place, nestled behind the famous Mama's Fish House(please make reservations before you arrive).

    This home has 3 bedrooms, 2 full baths, living room, dining room, dining area, fully equipped ...

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Paia
    53  reviews
    from $660 
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  • Palm Maui County permit STPH 20130018

    Maui North Shore Oceanfront Cottage 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 turtles swimming. Minutes ...

    • 2 bedroom
    • 1 bathroom
    • Sleeps 4
    Hawaii> Paia
    68  reviews
    from $525 
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  • Aloha Charm on Maui's North Shore

    SUPPORT MAUI THROUGH ALOHA TOURISM.
    Maui Winds II Paia - permit # STPHT2013/0019 is perfect for family and friends or a couple. This breezy and charming home invites rest and relaxation and offers exciting activities for top-notch athletes ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Paia
    65  reviews
    from $546 
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  • Paia Family Cottage - Walk to everything in Paia Town

    Walk to everything in Paia Town. Paia Family Cottage is well equipped, with comfortable indoor, and sweet outdoor living spaces for everyone. There is AC in all bedrooms and living room. And a yard where kids can play, with views out over the ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Paia
    74  reviews
    from $345 
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  • Luna House in the Heart of Paia, Maui

    PLEASE VISIT THE STATE / COUNTY WEBSITES FOR CURRENT COVID INFORMATION

    Located in central Paia, a short walk to beach, restaurants, bars, grocery, bank, boutiques. A thoughtfully remodeled c. 1934 plantation cottage, 832 SF, with modern...

    • 2 bedroom
    • 1 bathroom
    • Sleeps 4
    Hawaii> Paia
    43  reviews
    from $349 
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  • Ocean View 1 BR Cottage on Oceanfront Property. Permitted

    $320/night (+ tax 17.962%)(Permit # CP2001/0018 & HT ID TA-003-079-5776-01 & TMK 2-6-009-008).
    Minimum stay 7 nights. Want to stay fewer days? At certain times of the year, or for last minute bookings, we might waive the minimum nights ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Paia
    66  reviews
    from $320 
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  • Charming. permitted cottage, short walk to Paia town & beach.nSTPH 2013/0004

    Nestled on Baldwin Avenue, our plantation style one bedroom cottage provides convenient and comfortable accommodations for 2 people, with the amenities of Historic Paia Town and Paia Bay just a few minutes walk away and all areas of the Island ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Paia
    99  reviews
    from $195 
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  • Milo Maui County permit STPH 20130018

    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. Minutes away from world famous Ho'okipa Beach Park and Paia...

    • 4 bedroom
    • 2 bathroom
    • Sleeps 7
    Hawaii> Paia
    83  reviews
    from $709 
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  • Northshore - Paia Beach Town

    Walk to the beach and everything in Paia Town. Paia Family House is very spacious, well equipped, with a variety of comfortable indoor, and sweet outdoor living spaces for everyone! There's a yard where kids can play, and views out over the ...

    • 4 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Paia
    51  reviews
    from $800 
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  • Private Paia Studio in a Tropical Sanctuary, a short walk to Paia town & beach.

    This Private air conditioned studio is located on a newly remodeled ocean view estate, within walking distance to some of Maui's best restaurants and shops in the historic plantation town of Pa'ia. The property offers stunning views of both the ...

    • 0 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Paia
    23  reviews
    from $400 
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  • Charming Beach Cottage by Mama's Beach

    Grom's Hideaway is a charming cottage nestled in the heart of Kuau Point, the last little neighborhood 1 mile outside Paia(a 5 min drive), as you head out on Hana Highway.
    Grom's has 3 bedrooms (king, queen and two twins) and 1 Bath with an ...

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Paia
    29  reviews
    from $350 
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  • Luxurious ocean inspired studio in Paia short walk to Maui's coolest beach town

    This modern newly remodeled studio is hidden away in our tropical sanctuary we call Mangolani Inn. The studio has a king size bed, comfy love seat w/ driftwood coffee table & Mango wood dresser. Spa like custom tile bathroom and shower will ...

    • 0 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Paia
    9  reviews
    from $380 
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  • Paia beach house with huge ocean view and only one minute walk to Kuau beach

    Maui County Rental permit - STPH 2018/0003 (this is a legal, permitted Maui vacation rental)
    TA-066-523-9552-02 / GE-066-523-9552-02 TMK-260090240001

    It's a Beach House! A place to relax, unwind, listen to the breeze through the ...

    • 4 bedroom
    • 3 bathroom
    • Sleeps 8
    Hawaii> Paia
    25  reviews
    from $850 
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  • Adorable cottage near small beach

    Maui County Vacation Rental Permit: STPH2013/0010
    GE-066-317-9264-02/TA-066-317-9264-01
    TMK-260120340000
    Experience a delightful part of “old Hawaii” with all modern conveniences by staying at the Menehune Cottage or House in ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Paia
    9  reviews
    from $295 
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  • Lani Paradise Oceanfront Retreat with Private Pool

    Discover paradise with a private pool, surrounded by natural oceanfront scenery. Revel in the charm of this tastefully decorated 4-bedroom, two-story Villa and romantic 2-bedroom Cottage overlooking Maui's North Shore.

    This exclusive ...

    • 6 bedroom
    • 3 bathroom
    • Sleeps 12
    Hawaii> Paia
    1  reviews
    from $2,340 
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  • Paia Bay House, ocean front

    Oceanfront property in the heart of Paia town, surrounded by Coconut Trees with Coastline and Ocean views. The fenced in property offers great privacy and is only a few minutes walk away from Paia's Boutiques and Restaurants.
    The main house ...

    • 4 bedroom
    • 5 bathroom
    • Sleeps 8
    Hawaii> Paia
    10  reviews
    from $1,500 
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  • Aloha Glamp in Paradise

    Introducing the ultimate Maui adventure experience! Explore the magic of Maui in style and comfort with our premium 4x4 Jeep equipped with a rooftop tent, enabling you to seamlessly transition from one thrilling adventure to another while ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 1
    Hawaii> Paia
    2  reviews
    from $150 
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  • Quaint Paia Beach House with Ocean Views! Cold AC! Walk to town/beach!

    FULLY PERMITTED BY MAUI COUNTY
    STPH 2013-0026
    TA-073-017-7536-01, TA-134-951-1168-01

    Ice-cold Mistubishi Split A/C units added 5/17. New entry door added 4/17.

    This listing is for the upstairs Bay View unit. The upstairs unit...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Paia
    151  reviews
    from $310 
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  • Oceanfront: Large Private Beach House - Maui North Shore

    TAT 199-207-5264-01,GE199-207-5264-01 Lawful Transient Vacation Rental Use 10/30/2009
    Hale Ola is an original island-style beach house, recently remodeled, with beautiful panoramic views of the West Maui mountains and Kanaha Beach Park. The ...

    • 4 bedroom
    • 3 bathroom
    • Sleeps 8
    Hawaii> Paia
    39  reviews
    from $1,000 
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  • Plantation Style cottage short walk to beach and town nPermit STPH2013/0004


    Nestled on Baldwin Avenue, this two bedroom cottage provides convenient and comfortable air conditioned accommodations, comfy queen sized beds and a/c units in each bedroom, with the amenities of Historic Paia Town and Paia Bay just a 5 ...

    • 2 bedroom
    • 1 bathroom
    • Sleeps 4
    Hawaii> Paia
    93  reviews
    from $220 
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  • Gingerbread House-Less than a mile from Paia town and all North Shore beaches

    This unique and romantic two story, one bedroom house is nestled in a mango tree. The house is an A-frame structure with high ceilings and skylights making it bright and airy. It is located less than a mile from the bohemian town of Paia and all...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 3
    Hawaii> Paia
    49  reviews
    from $280 
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  • #1 Family & Windsurf Friendly Private Sandy Beachfront Home on North Shore


    TAT 199-207-5264-01,GE199-207-5264-01 Lawful Transient Vacation Rental Use 10/30/2009

    NEW UPDATE!!- newly remodeled Kitchen with all new appliances including: Double Oven, Wine Fridge, Breakfast bar overlooking the ocean- ahhhh!! ...

    • 4 bedroom
    • 3 bathroom
    • Sleeps 8
    Hawaii> Paia
    10  reviews
    from $1,000 
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  • BEAUTIFUL NEW Beach-chic condo with AC 1 mile from Paia & Steps to Mama's Beach

    Ku'au Plaza is a very small, friendly, quiet 30 unit condo complex; the only one of it's kind on Maui's north shore. Our fully remodeled, Beach Chic style condo is ideally nestled next to Mama's Beach & tide pools and the famous Mama's Fish ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 4
    Hawaii> Paia
    36  reviews
    from $258 
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  • Maui Modern North Shore Beach Condo - Walk to Mamas Fish House! AC, Fast WiFi

    A beautiful, modern one bedroom condo located walking distance to the famous Mama's Beach on Maui’s majestic North Shore! Located in Paia, this unit is the perfect home away from home for exploring the delights of Maui's North Shore and ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Paia
    73  reviews
    from $179 
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  • 3 Bedroom Home - in Paia Town - Walk to it All

    If you want to be in Paia, or minutes to Ho'okipa or Sprecklesville, you'll like this location. This is the relaxed, non-touristy Hawaiian experience. Plus, Paia is the north shore hub for all sports wind and wave. And, Paia is a walk-able ...

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Paia
    77  reviews
    from $750 
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  • Gorgeous! Oceanfront with Pool and Hot-Tub - Permitted

    Maui County Rental permit - STPH 2013/0008
    TA-048-493-9776-01 / GE-048-493-9776-01
    TMK-260040080000
    WALK TO EVERYTHING IN PAIA TOWN!
    The setting is just stunning! Enter the back gate, and the first view looking through the glass ...

    • 4 bedroom
    • 4 bathroom
    • Sleeps 6
    Hawaii> Paia
    31  reviews
    from $1,500 
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  • Kuau Cottage 1 Bedroom Clean, New apartment close to Ho'okipa and Paia

    Clean, newly built 1 bedroom/1 bath with super fast internet and A/C. Situated in a quiet neighborhood in Kuau, away from the hustle and bustle of Paia but still just a short 1 mile car journey from the town. Kuau Beach and Mama’s Beach are ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 4
    Hawaii> Paia
    8  reviews
    from $260 
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  • Gorgeous Oceanfront Paia Bay Home

    Nalu House is the perfect home for a Maui vacation. This house, a beautiful designer remodeled home, combines old Hawaii's charm with all the modern amenities. Sit outside on a private covered lanai on relaxing lounge chairs to watch the ...

    • 2 bedroom
    • 3 bathroom
    • Sleeps 4
    Hawaii> Paia
    8  reviews
    from $2,300 
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