25 Best Paia Vacation rentals on Holiday Lettings - House rentals

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1,113 Vacation rentals

6

Vacation private room in Paia

Maui / Paia

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 0.5 mi
  • Car not necessary
SUMMARY: No car? Don't feel like driving on vacation? Want to save on car rental? This is THE PERFECT place for you. My place is 5min walking distance to the Beach, restaurants and dining, town center, art and culture, great views, family-friendly activities. You’ll lo …see more

from $129 / night

$801 / week

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from $129 / night

7

Private room rental in Paia

Maui / Paia

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 0.5 mi
  • Car not necessary
SUMMARY: No car? Don't feel like driving on vacation? Want to save on car rental? This is THE PERFECT place for you. My place is 5min walking distance to the Beach, restaurants and dining, town center, art and culture, great views, family-friendly activities. You’ll lo …see more

from $127 / night

$801 / week

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from $127 / night

(5) Very Good 

24

Vacation apartment in Paia

Maui / Paia

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 0.5 mi
  • Child friendly
Suite w/full private bathroom in shared 2 bed 2 bath condo. Features queen-size bed, TV & free Wi-Fi. Parking may be assigned or unassigned. Shared kitchen, living room & lanai. Laundromat on site. 2 guests max. Close to Ho'okipa & Baldwin Beach, Paia Bay, Twin Falls. …see more

from $105 / night

$735 / week

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from $105 / night

(5) Very Good 

20

Paia Vacation private room rental

Maui / Paia

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
Suite w/full private bathroom in shared 2 bed 2 bath condo. Features queen-size bed, TV & free Wi-Fi. Parking may be assigned or unassigned. Shared kitchen, living room & lanai. Laundromat on site. 2 guests max. Close to Ho'okipa & Baldwin Beach, Paia Bay, Twin Falls. …see more

from $100 / night

$700 / week

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from $100 / night

14

Paia Vacation home accommodation

Maui / Paia

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Child friendly
STPH2013/0004 Nestled on Baldwin Avenue, this two bedroom cottage provides convenient accommodations, ( comfy queen sized beds in each bedroom), with the amenities of Historic Paia Town and Paia Bay just a few minutes walk away and all areas of the island within easy d …see more

from $210 / night

$1,470 / week

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from $210 / night

(4) Excellent 

51

Home rental in Paia

Maui / Paia

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden
Grom's Hideaway is three bedrooms with four beds (king, queen and two twins). There's everything you need to have a relaxing and exciting vacation with your friends or family. Enjoy the a beautiful morning at the beach and some wonderful surf, your private outdoor showe …see more

from $199 / night

$1,393 / week

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from $199 / night

(6) Very Good 

16

Paia Vacation home rental

Maui / Paia

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
What a Perfect Location for Your Family and Extended Family ! We Welcome Smaller Groups (2-6) and Small Families (2-6). We are a stone's throw away from the Beach. Hale Makai With 3,000 square feet offers beautiful views of the North Shore of Maui. A large front yard …see more

from $825 / night

$5,775 / week

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from $825 / night

(18) Excellent 

60

Vacation home in Paia

Maui / Paia

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Child friendly
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 town. The north shore has no …see more

from $245 / night

$1,995 / week

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from $245 / night

(2) Excellent 

7

Cottage rental in Paia

Maui / Paia

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
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. Minutes from world famous Ho'okipa beach park.The property has the perfect blend of privacy and s …see more

from $350 / night

$2,450 - $2,625 / week

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from $350 / night

(1) Very Good 

12

Home rental in Paia

Maui / Paia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Pet friendly
This unique and romantic one bedroom cottage is nestled in a mango tree. The house is an A-frame structure with high ceilings and skylights making it bright and airy. The house is located less than a mile from the bohemian town of Paia and is in the middle of all North …see more

from $225 / night

$1,425 - $1,565 / week

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avg. 2 hours 37 minutes

from $225 / night

(1) Excellent 

19

Vacation home in Paia

Maui / Paia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
This is an adorable, two bedroom (optional ONE bedroom-see below) house with high, vaulted ceilings and shiny wood floors. The house is a half block off Hana Highway, less than a mile from Paia town and all North Shore Beaches. The nearest beach access is Tavares Beach, …see more

from $265 / night

$1,750 - $2,030 / week

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avg. 2 hours 37 minutes

from $265 / night

(2) Good 

24

Vacation home rental

Maui / Paia

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Hale Ola is an original island-style beach house with beautiful panoramic views of the West Maui's and Kanaha Beach Park. This generous sized one acre beachfront property, well known as "Honey Bun's", features your own fabulous white Sandy beach cove with a private wind …see more

from $750 / night

$5,250 / week

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from $750 / night

16

Vacation apartment in Paia

Maui / Paia

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
This is an adorable ONE (or TWO) bedroom cottage that has high vaulted ceilings, and shiny wood floors. The house is a half block off Hana Highway, one the mountain side, less than a mile from the bohemian town of Paia and is in the middle of all North Shore Beaches. We …see more

from $215 / night

$1,375 - $1,655 / week

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Responds fast!
avg. 2 hours 37 minutes

from $215 / night

(21) Very Good 

37

Cottage rental in Paia

Maui / Paia

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.16 mi
  • Child friendly
MAUI NORTH SHORE OCEAN VIEW Maui by the Sea is a beautiful vacation rental - an ideal ocean-view cottage located between Paia and Hookipa, on Maui's scenic and exciting North Shore. Our two-story plantation-style cottage has gorgeous views of a sapphire ocean with danc …see more

from $275 / night

$1,925 / week

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avg. 1 hour 2 minutes

from $275 / night

12

Paia Vacation home rental

Maui / Paia

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
  • Air conditioning
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.The property has the perfect blen …see more

from $575 / night

$4,025 - $4,200 / week

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from $575 / night

10

Paia Vacation home rental

Maui / Paia

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
Oceanviews from each window! Only 50 steps from the wonderful Baby Beach end of Baldwin Beach (mile long sandy beach--best on Maui's north shore). One of the few truly ocean front cottages on Maui's north shore. This is a private cottage with no other rental downstai …see more

from $325 / night

$2,275 / week

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from $325 / night

(8) Excellent 

76

Paia Vacation home rental

Maui / Paia

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
You can't be closer to more fun than this location! MAMA'S FISH HOUSE and its gorgeous beach walkable and world-famous HO'OKIPA is just a minute beyond Mama's. Less than five minutes away is historic PAIA TOWN with it's shopping, dining, art galleries and beaches. Right …see more

from $499 / night

$3,493 / week

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from $499 / night

25

Vacation condo rental

Maui / Paia

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
Sugar Cove sits beachfront with launch access for windsurfers and kiters. Families love Baby Beach / Baldwin Beach, just a short walk down the street. This property is four manicured acres with only 18 oceanfront town homes (only 3 are available for vacation renting). …see more

from $600 / night

$4,200 / week

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Responds fast!
avg. 3 hours 12 minutes

from $600 / night

6

Vacation studio in Paia

Maui / Paia

Studio 4 1 night min

  • Studio
  • Sleeps 4
  • 1 night min
  • Child friendly
Located in Spreckelsville on Maui’s beautiful North Shore, Sprecks Plantation House is the perfect place to enjoy all that Maui has to offer. Our updated accommodations offer a charming, tropical ambiance and private lanais (Hawaiian for patio). Listen to the gentle rus …see more

from $170 / night

$1,190 / week

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from $170 / night

29

Vacation home with swimming pool in Paia

Maui / Paia

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.16 mi
  • Swimming pool
This property has been voted TOP 10 MAUI VACATION RENTALS by Trip Adviser 05/2015 Maui Plantation Beach Home, Spreckelsville, Paia is a only 2-3 min walk to Baby Beach, Maui's best swimming beach and voted second best beach on Maui! It's not just a home, it's a lifesty …see more

from $995 / night

$6,965 / week

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Responds fast!
avg. 2 hours 59 minutes

from $995 / night

12

Paia Vacation home rental

Maui / Paia

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • Child friendly
Permitted vacation rental STPH2013/004, 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 Paia Town and Paia Bay j …see more

from $180 / night

$1,260 / week

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from $180 / night

25

Vacation condo rental

Maui / Paia

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
Absolutely the best North Shore location! Sugar Cove sits beachfront, with launch access for windsurfers and kiters. Families love Baby Beach / Baldwin Beach, just a short walk down the street. This property is four manicured acres of grounds with only 18 oceanfront …see more

from $600 / night

$4,200 / week

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Responds fast!
avg. 3 hours 12 minutes

from $600 / night

20

Vacation home in Paia

Maui / Paia

3 6 6 nights min

  • 3 bedrooms
  • Sleeps 6
  • 6 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Permitted vacation rental STPH 2015/0002 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 fiftee …see more

from $335 / night

$2,345 / week

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Responds fast!
avg. 3 hours 2 minutes

from $335 / night

(2) Excellent 

98

Paia Vacation home rental

Maui / Paia

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Paia Surf! Experience the ultimate vacation spot on one of the jewels of the Hawaiian island chain from the comfort of a newly-remodeled house on Maui's famed north shore. You'll enjoy the finest land & water attractions, spectacular cuisine, and the best kind of R&R. Y …see more

from $649 / night

$4,316 / week

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Responds fast!
avg. 3 hours 24 minutes

from $649 / night

18

Vacation camper van in Paia

Maui / Paia

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Air conditioning
Explore all of Maui’s beautiful sites in a pristine 2016 4x4 Jeep Compass and connect with nature. Wake up to an amazing ocean view and star gaze in our Yakima Skyrise rooftop tent and a built-in mattress. Discover all the trails, waterfalls & beautiful beaches with thi …see more

from $160 / night

$1,100 / week

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from $160 / night

34

Vacation home with swimming pool in Paia

Maui / Paia

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 6 mi
  • Swimming pool
  • Child friendly
WALK TO EVERYTHING IN PAIA TOWN! The setting is just stunning! Enter the back gate, and the first view looking through the glass door, across the entry area, and beyond the patio is of the ocean framed by palm trees, and the sandy beaches of Paia, Baldwin and Spreckels …see more

from $1,000 / night

$7,000 / week

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Responds fast!
avg. 3 hours 12 minutes

from $1,000 / night

(54) Excellent 

110

Paia Vacation home rental

Maui / Paia

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Welcome to the newly remodeled Paia Surf House, which easily accommodates parties of 5-9 (unused parts of the house can be closed off, saving $$$) – or splurge and make it all just a honeymoon palace for two. When you're at Paia Surf, you can stash the car keys for days …see more

from $849 / night

$5,645 / week

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Responds fast!
avg. 3 hours 24 minutes

from $849 / night

(2) Excellent 

77

Vacation home in Paia

Maui / Paia

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden
The space Paia Surf! Experience the ultimate vacation spot on one of the jewels of the Hawaiian island chain from the comfort of a newly-remodeled house on Maui's famed north shore. You'll enjoy the finest land & water attractions, spectacular cuisine, and the best kin …see more

from $749 / night

$4,980 / week

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Responds fast!
avg. 3 hours 24 minutes

from $749 / night