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Family-friendly vacation rentals in Paia

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Paia

  • Total vacation rentals

    Explore 30 vacation rentals in Paia

  • Nightly prices starting at

    Paia vacation rentals start at G$46,012 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,700 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Paia vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Paia rentals

  • 4.8 Average rating

    Paia stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated family-friendly rentals in Paia

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
Guest suite in Paia

Paia Surf Suite. Quiet beach access & walk to town

A private beach path 150m from your door! Walk to the surf! Less than 15 minute walk to the charming cafes of Paia town. Located at the rear of an ocean-front property on the beautiful North Shore, 5 minutes from world famous Ho.okipa. The rental contains 1 bedroom, 1 bathroom, living area & private lanai (patio). The kitchenette is equipped with mini-fridge, toaster oven and microwave. On the start of road to Hana, central to everything! NOT affected by Bill 9. Your booking is 100% secure!

4.9 out of 5 average rating, 199 reviews
Top guest favorite
Home in Haiku-Pauwela

Live Like a Local; near Coffee, Road to Hana and Haleakala

Grab a coffee and drive to the beach to catch waves or watch sea turtles nesting in the sand. This peaceful home with a private yard, outdoor shower, and fun surfboard fence is a great base for exploring the Road to Hana or Haleakala. Located on the quiet north shore of maui, 1 hour from popular tourist areas. Ideal for returning maui visitors who want to stay on the north shore or guests splitting their stay between 2 sides of the island of Maui. Sleeps: 4 guests max (including kids/infants)

4.97 out of 5 average rating, 295 reviews
Superhost
A vibrant green chair provides a seating option next to a modern entertainment center. Palm and pineapple decor are featured on a stylish cart. Wall art, including framed fish illustrations, adds a tropical touch, while natural light flows through the nearby sliding glass door.
Condo in Paia

Kuau Plaza Paradise in Paia 3

Tucked away on Maui’s north shore, this cozy hideaway offers a relaxed, local vibe—far from the resort crowds. Just steps from Mama’s Fish House and Mama’s Beach, you’ll be close to some of the island’s most stunning and uncrowded spots. Ho’okipa Beach, a world-famous surf and turtle-watching destination, is just minutes away, and downtown Paia—with its eclectic shops and cafés—is only a mile down the road. If you're seeking an escape with true island character, this is your kind of place.

4.83 out of 5 average rating, 239 reviews
Guest favorite
The exterior of a private cabin is surrounded by lush greenery, featuring vibrant tropical plants. A porch with rocking chairs offers a welcoming spot to relax. The cabin's distinctive architecture includes a sloping roof and decorative wooden details, providing a harmonious blend with the natural environment.
Farm stay in Haiku-Pauwela

Ocean View - Private Cabin

NOTE: Many oceanfront condominiums are currently under threat of a phase-out. Farm stays are a "Permissible Use" on agricultural bona fide farms by State of Hawai'i law. Be assured your reservation here will be safe from government interference. Located on a working coffee plantation and food forest, this restored cabin is private but close to lots of upcountry activities. Kitchen, ocean view, open concept, great lanai spaces, plenty of off-street parking, access to private hiking trails.

4.97 out of 5 average rating, 332 reviews
Top guest favorite
A charming studio cottage with a distinctive shingle exterior is set among lush greenery. A golden retriever rests on the pathway in front, alongside large trees that provide shade. A vibrant green door invites guests into the cozy interior.
Farm stay in Haiku-Pauwela

Adorable Gingerbread House Farm Stay, Makawao

This LEGALLY PERMITTED Farm Stay has the lush beauty and privacy,, without the drive to Hana! Only 15-20 minutes to the airport, 10 minutes to beaches, 2 minutes to restaurants and shops...on a private gated property with organic nursery. Seasonal stream in the back yard. Simply BEAUTIFUL! We gave 8.5 acres of diversified farm-fruit, water lilies, 10,000 sq ft greenhouse) Comes with a FREE FARM TOUR and/or LABYRINTH WALK with every booking! Permit Number STMP 2015 / 0001 SUP2 2013 / 0013

4.94 out of 5 average rating, 685 reviews
Guest favorite
The exterior view shows a charming gray house with white trim and multiple windows. Flower boxes are mounted under the windows, and a concrete pathway leads past the property. Lush greenery and tall trees are visible in the background under a clear blue sky.
Home in Haiku-Pauwela

Quaint 4-bedroom in Ha'iku, Maui

Bring the whole family to the north shore of Maui and stay in our quaint, plantation-era home! At Kihau Gardens (Maui County STRH Permit #2019/0001 and Hawai'i State TAT #T-036-968-8576) we offer a unique home. On each side of a carport, there are two bedrooms, a living area, a small office space, and one and a half baths. Our home in Ha'iku is the perfect stay for two small families who want to explore the north shore, upcountry, Haleakala crater, and the epic drive to Hana.

4.9 out of 5 average rating, 173 reviews
Top guest favorite
An open concept living space is displayed, featuring a comfortable leather sofa and a wooden dining table. Large sliding glass doors invite natural light, while a modern kitchen is visible in the background. Ceiling fans and decorative elements enhance the airy ambiance.
Farm stay in Haiku-Pauwela

Kalani at Haiku Garden Cottages Farm Sanctuary

Welcome to Haiku Garden Cottages, a licensed Farmstay and B&B on Maui’s North Shore (Permit #BBPH2017/0002). Kalani is a charming cottage where you can sip coffee on the lanai, wander garden paths, harvest seasonal fruit, and settle into island rhythms. Enjoy ocean and garden views, a private outdoor shower, and relaxed indoor-outdoor living—just minutes from Haleakalā, the Road to Hāna, beaches, hiking trails, restaurants, and farmers markets.

4.94 out of 5 average rating, 456 reviews
Top guest favorite
The living area features a wooden dining table surrounded by four chairs, with a comfortable beige sofa positioned nearby. Large glass doors provide natural light and views of the backyard, framed by vibrant greenery. A flat-screen TV is mounted on the wall opposite.
Condo in Paia

Locally-Owned Eco-Friendly Condo on Road to Hāna

Kūʻau on Maui's north shore offers uncrowded access to unique beaches and the best proximity to Mama's Fish House, Pāʻia town, Road to Hāna, Haleakalā National Park, and Kahului airport. Designed with environmentalist principles, every detail has been mindfully chosen. This local family-owned small business proudly supports other local businesses. I welcome people of all backgrounds to connect with the natural environment and cultures of Maui.

4.93 out of 5 average rating, 516 reviews
Superhost
A spacious living area features a modern couch adorned with decorative pillows. Large glass doors open to a lush lawn area, allowing natural light to fill the room. A ceiling fan and a small dining table complement the welcoming ambiance, while tropical plants add a touch of greenery.
Condo in Paia

Paradise In Paia 2

This lovely, recently updated condo on Maui's beautiful North Shore is located at Kuau Plaza in Paia. If you are looking for a great location, steps from the beach and want to experience the real Maui, look no further. This first floor unit offers an expansive lawn with a direct path to the beach. The updated decor is mid century modern with tropical accents to honor the building’s history which is reminiscent of Old Hawaii.

4.85 out of 5 average rating, 250 reviews
Top guest favorite
The exterior of a two-story home is displayed amid lush greenery. A spacious deck is highlighted with white railings and a pergola, complementing the tranquil surroundings. The sky is bright with scattered clouds, enhancing the feeling of openness and serenity.
Home in Haiku-Pauwela

The Art Estate, Haiku Maui Hawaii

Our spacious, open-floor-plan home has a contemporary style. The secluded 17-acre, lush, tropical estate has exotic varieties of Bamboo, Palms, Avocados, and various fruit trees. Located on the grounds is a private, functioning, award-winning art studio creating films, photography, video installations, and sculpture. If you are looking to explore, we are just a quick ten-minute drive to the best beaches on the North Shore!

4.92 out of 5 average rating, 103 reviews
Top guest favorite
A modern, two-bedroom home is showcased, featuring a covered lanai with a dining area for six. Large windows provide views of the surroundings, while the exterior combines wood and blue siding against a bright sky and greenery.
Home in Haiku-Pauwela

Peaceful and Spacious; North Shore Maui

New, spacious two-bedroom home in Ha'iku, Maui (Permit STPH20200003). With beautiful ocean views and peaceful surroundings, located on the Northshore of Maui, this is the perfect place to stay to explore the Road to Hana, the Northshore, and upcountry Maui. Perfect for two couples or a family, you'll have everything you need to explore the island and a peaceful living area to relax following a day of adventuring.

4.98 out of 5 average rating, 160 reviews
Top guest favorite
A bright bedroom features a spacious bed adorned with white linens and green accents. Large windows provide natural light and views of the surrounding greenery. A small table with two chairs is positioned nearby, complemented by soft drapes that frame the windows.
Guesthouse in Makawao

Serene Starting Point for Roaming Island Wide

The Orchid Wing is a private 2-bedroom guest wing within our intimate historic inn, ideal for families or close friends ready to reconnect and roam. Vintage charm, views of Maui’s largest Norfolk pine, lush gardens, beach gear, Haleakalā blankets, and daily brekky baskets create a warm Upcountry home base for island adventures. No indoor common area. Please see floor plan in photo gallery. BBMPT20200001

4.95 out of 5 average rating, 126 reviews

Popular amenities for Paia family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favorite
A charming cottage is set on a spacious lawn, surrounded by lush greenery. The exterior features a broad lanai with white railings, providing a welcoming entrance. Tropical trees and plants frame the property, contributing to a serene atmosphere.
Guesthouse in Haiku-Pauwela

Maile Bungalow- County Licensed

4.93 out of 5 average rating, 152 reviews
Guest favorite
A distinguished bamboo cottage is elevated on stilts, surrounded by lush tropical vegetation. Wooden decks wrap around the structure, providing access to outdoor seating areas. Large windows offer views of the surrounding greenery, harmonizing the indoor and outdoor environment.
Cottage in Haiku-Pauwela

Hawaiian DreamTemple- Tropical Oasis BBPH20120004

4.83 out of 5 average rating, 219 reviews
Guest favorite
A clear view of a swimming pool is presented, surrounded by lounge chairs and tropical greenery. Palm trees frame the scene, with the ocean visible in the background under a bright blue sky dotted with clouds.
Condo in Kihei

3BR spacious Condo with Ocean View in top location

4.92 out of 5 average rating, 194 reviews
Guest favorite
A scenic view showcases swaying palm trees against a vibrant blue sky, with a glimpse of the ocean in the background. Lush greenery frames a pool area, inviting relaxation, while the buildings provide a residential atmosphere. The beach appears just beyond the manicured lawns.
Condo in Kihei

Lovely Oceanfront Condo with pool

4.92 out of 5 average rating, 174 reviews
Top guest favorite
Apartment in Kihei

Family-friendly Oceanview beach retreat | AC, Pool

4.89 out of 5 average rating, 212 reviews
Guest favorite
A large swimming pool is surrounded by lounge chairs and tropical landscaping, offering views of palm trees and the ocean. The area features a sun deck, umbrellas, and a shaded seating spot, contributing to a relaxed resort environment.
Condo in Wailea

Spacious comfy unit Netflix & huge pool Maui Hill

4.92 out of 5 average rating, 170 reviews
Guest favorite
An aerial view of the Maui Sunset beachfront complex reveals manicured lawns and vibrant tropical landscaping. A central pool is surrounded by palm trees, with direct beach access visible in the background. Tennis courts are located adjacent to the lush green area.
Condo in Kihei

Spacious 2BR + Private Alcove @ Maui Sunset, AC

4.9 out of 5 average rating, 105 reviews
Top guest favorite
A sandy beach stretches along the coastline, framed by tall palm trees swaying gently. Gentle waves lap against the shore, creating a serene atmosphere. In the distance, lush green hills rise under a partly cloudy blue sky, enhancing the natural beauty of the location.
Condo in Wailea

Very Comfortable Kamaole Sands Condo Sleeps 4

4.99 out of 5 average rating, 150 reviews

Family- and pet-friendly home rentals

Top guest favorite
A sunlit swimming pool is framed by lush green grass, leading to a well-designed single-story home with a distinct round roof. The expansive landscape stretches in the background, providing a view of the ocean and distant mountains under a clear blue sky.
Home in Kula

Kula Jewel - Pool, Hot Tub & Awesome Views!

4.93 out of 5 average rating, 420 reviews
Guest favorite
An open living space features a comfortable bed with soft blue linens, a stylish fold-out loveseat, and a large area rug. A fully equipped kitchen with wooden cabinets and a breakfast bar is visible, complemented by natural light from nearby windows.
Guest suite in Wailuku

Oceanview, Banana Bread, Hot Tub & Sauna near OGG

4.89 out of 5 average rating, 569 reviews
Guest favorite
Cottage in Maui County

Haleakala Cottage - private hot tub, pool access

4.96 out of 5 average rating, 232 reviews
Guest favorite
A bright living area is showcased with large glass doors offering access to an outdoor space. Comfortable seating is provided by a gray sofa and wicker chairs, accented with blue and patterned cushions. A glass coffee table is placed centrally, complemented by a mounted flat-screen TV.
Condo in Kihei

Sleeps 8 Ocean View 3bth Kamaole Beach HOT TUB

4.86 out of 5 average rating, 107 reviews
Guest favorite
A cozy outdoor deck is showcased, featuring two wicker chairs and a small table, inviting relaxation. The inviting turquoise door stands adjacent to a wall with the word 'Aloha' elegantly displayed. String lights add a warm touch above, surrounded by tropical greenery.
Home in Kihei

Enjoy paradise living at the THERE Maui House!

4.92 out of 5 average rating, 146 reviews
Superhost
Home in Wailuku

3B2B w/HotTub FamilyComfort HawaiianaCharm Central

4.81 out of 5 average rating, 113 reviews
Top guest favorite
The open living area showcases vaulted ceilings and warm wood beams. A modern kitchen island with a marble finish is complemented by stylish pendant lights. A cozy seating area invites relaxation, while large windows offer views of the surrounding landscape, enhancing the bright and airy atmosphere.
Townhouse in Wailea

Beautiful Wailea Ekolu Townhouse-Perfect Get-Away

4.97 out of 5 average rating, 145 reviews
Top guest favorite
A serene beach scene at sunset showcases soft hues of orange, pink, and purple in the sky. Silhouetted figures walk along the shoreline, while a tall palm tree stands nearby, framing the tranquil landscape and creating a sense of calm.
Condo in Kihei

Ocean View Superior Deluxe - 200

4.84 out of 5 average rating, 431 reviews

Family-friendly home rentals with a pool

Top guest favorite
A spacious living area features a light grey sofa and a wooden coffee table positioned on a natural fiber rug. Large glass doors open to a patio with ocean views, while a flat-screen TV sits atop a console. Neutral curtains frame the windows, creating an airy atmosphere.
Condo in Maalaea

Coastal Dream Oceanfront Condo!

4.98 out of 5 average rating, 124 reviews
Top guest favorite
A vintage toy van is positioned on a sandy beach, facing a vibrant sunset over the ocean. Warm golden light reflects off the waves, creating a serene scene. The gentle surf adds a sense of calm to the atmosphere, with small ripples lapping at the shore.
Condo in Wailea

Groovy bright condo 2 bed / 2 bath South Kihei

4.93 out of 5 average rating, 205 reviews
Guest favorite
An aerial view captures the coastal Menehune Shores complex, showcasing its resort-style architecture alongside the ocean. Lush green lawns extend towards the shore where gentle waves lap against the sandy beach. The backdrop features the expansive landscape of Maui, highlighting both land and sea.
Condo in Kihei

Stylish Kihei Condo in Oceanfront Resort Complex

4.99 out of 5 average rating, 147 reviews
Guest favorite
A private beachfront lawn is shown, featuring several lounge chairs arranged on lush green grass. Umbrellas stand nearby, providing shade. A backdrop of palm trees frames the view of the ocean, with gentle waves lapping against the shore under a partly cloudy sky.
Condo in Kihei

Oceanfront Condo on magic Sugar Beach - Ocean View

4.93 out of 5 average rating, 219 reviews
Guest favorite
A modern loft interior features a spacious living area with a light grey sectional sofa adorned with various blue and white throw pillows. A simple wooden dining table with teal seating is visible alongside a kitchen with a white island. Large windows allow natural light, and a decorative wall clock adds charm.
Condo in Kihei

Live, Love, Loft in Beautiful Maui

4.98 out of 5 average rating, 201 reviews
Top guest favorite
A picturesque view captures a beach at sunset with vibrant orange and purple hues in the sky. Swaying palm trees line the shoreline, where beachgoers can be seen enjoying the golden sand and gently lapping waves. The grassy area near the beach is dotted with lounge chairs.
Condo in Wailea

Mana Kai Palms Oceanfront Condo: Keawakapu Beach

4.97 out of 5 average rating, 105 reviews
Guest favorite
A serene bedroom features a queen bed adorned with decorative pillows in calming colors. An ocean-themed quilt complements the space, while a tray holding a teal cup and a pink plate rests on the bed. Art depicting a sea turtle and a beach scene decorates the walls.
Condo in Kihei

Only $125/Night! September Openings! Kihei

4.95 out of 5 average rating, 110 reviews
Guest favorite
Condo in Maalaea

Oceanfront, Ground Floor Condo Steps to Ocean

4.94 out of 5 average rating, 127 reviews

When is the best time to visit Paia?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$121,933 GYDG$104,573 GYDG$120,050 GYDG$94,116 GYDG$100,181 GYDG$115,031 GYDG$103,946 GYDG$93,698 GYDG$94,116 GYDG$93,489 GYDG$100,181 GYDG$118,586 GYD
Avg. temp23°C23°C23°C24°C25°C26°C27°C27°C27°C26°C25°C24°C

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