Family-friendly holiday rentals in Kapalua

4.97 out of 5 average rating, 105 reviews

Experience Tropical Paradise at Napili Bay

✨ Welcome to Where Maui Magic Meets Comfort ✨ Experience Luana, the Hawaiian practice of relaxing, enjoying, and finding happiness. Just 200 steps from the inviting turquoise waters of Napili Bay, this luxurious 3BR/2.5BA townhome at the Residences at Napili Bay is your gateway to one of Maui’s most enchanting coastlines. Imagine snorkeling alongside sea turtles, sipping cocktails on your private lanai (deck), and falling asleep in the comfort of Westin Heavenly Beds with the cool trade winds—o

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A lush green lawn is framed by swaying palm trees, leading toward a vibrant blue ocean. In the background, a thatched-roof structure is visible, alongside tranquil water and distant islands. The bright sky adds to the serene coastal atmosphere.

4.99 out of 5 average rating, 127 reviews

Ocean View Studio steps away from Napili Bay! w/AC

Beautiful ocean view, air-conditioned studio is located at Napili Shores Resort! Napili Shores is a stunning, beautifully maintained, ocean front resort that offers 2 pools, hot tub, an onsite surf and snorkel rental shop, 2 restaurants, and is steps away from both Napili Bay and Kapalua Bay. The unit is located on the 2nd floor with privacy and an ocean view, with a king size bed, 55" TV, and a full size, fully equipped kitchen. The unit also includes Tommy Bahama beach chairs for guests use.

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4.97 out of 5 average rating, 259 reviews

A two-story green house is surrounded by lush tropical gardens, showcasing large windows that provide a bright interior. A spacious deck extends from the structure, offering views of the vibrant foliage and the inviting outdoor space.

Cabin in Maui County

★Rainbow Lookout - PRIVATE HOT TUB+ACCESS TO POOL

This Stunning North Shore Maui hideaway is surrounded with lush fruit and flower gardens, coconut palms, banana trees, and has easy access to all there is to do on this magnificent island. Stargaze … soak in your own private hot tub with a chilled glass of wine and enjoy a once-in-a-lifetime experience. The 'real' Maui:)! ★Jump Start to The to the Road to Hana! ✔ ★New Cold Central AC ✔ ★Cliff Walk ✔ ★Ocean View✔ ★Private Hot Tub ✔ ★44 ft Swimming Pool ★King Bed ✔ ★Sunrise View✔ ★Star Gazing✔

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A clear blue sky and palm trees frame a sparkling pool surrounded by lounge chairs. A thatched-roof pavilion stands nearby, providing a shaded area with tropical landscaping all around, emphasizing the inviting atmosphere of the resort.

4.88 out of 5 average rating, 153 reviews

Summertime in Napili Shores-Cozy, Oceanside Condo

Napili is the perfect place for your Maui vacation. This beautiful condo’s location is the best mix of resort life and local vibe. Our newly renovated condo is located oceanside and is only a short walk to soft, sandy, quiet beaches. This second floor, corner unit overlooks the beautiful gardens, the tranquil Koi pond and resort swimming pool. The private lanai is the perfect setting to relax and listen to the birds sing, the rustling of the Koi pond and take in the magical Maui ocean breeze.

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Bungalow in Napili-Honokowai

A charming bungalow is surrounded by lush greenery and tropical landscaping, with tall palm trees framing the entrance. A dark blue SUV is parked in the driveway, positioned beside the front door. Bright sunlight highlights the vibrant plants and landscaping, creating a welcoming atmosphere.

4.99 out of 5 average rating, 220 reviews

Peaceful Maui Bungalow | Ka Hale Aloha-Love Shack

Escape and fall in love with “Ka Hale Aloha-The Love Shack” where paradise awaits you....This adventurous hideaway will leave you feeling refreshed, relaxed and more alive!! Experience all the life & Aloha the island of Maui has to offer in your private detached bungalow located on an old 8 acre fruit plantation turned condos, steps to the ocean & walking distance to 2 beaches. Ka Hale Aloha will make you feel like you’re truly living the island life. * Check us out on IG at @thoughtfulstays

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A spacious living area is furnished with a seven-piece sectional sofa and a comfortable twin daybed. A coffee table rests on a patterned area rug. Floor-to-ceiling windows provide garden views, while a ceiling fan adds comfort to the inviting ambiance.

4.99 out of 5 average rating, 162 reviews

NEWLY REMODELED OCEAN VIEW CONDO, STEPS FROM BEACH

Your next relaxing Lahaina escape awaits at this stunning 1-bedroom, 2-bath vacation rental condo - steps away from Kapalua Bay Beach & located next to The Resort at Kapalua Bay (formerly Montage). Your group of up to 6 guests will love returning to the comfort of this home, offering over 1,100 sq ft of living space. With easy access to championship golf courses, fine dining, walking/hiking paths, spas, & several bays/beaches for snorkeling, surfing, & relaxing, this is the perfect home base.

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4.96 out of 5 average rating, 235 reviews

Spectacular views, prime location Kapalua, Maui.

Prime Kapalua location this stylish, romantic two-level villa offers elevated panoramic ocean views. Wake in a luxurious California King bed to stunning Pacific sunrises and fall asleep to the soothing sound of ocean waves. Relax on your private upstairs lanai or spacious patio and take in the breathtaking views. Walk to beaches, scenic trails and dining. Peaceful, magical- your perfect Maui escape. A/C on both levels and bright, airy interiors, this villa is a tranquil upscale Maui retreat.

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A lush outdoor garden area is visible, featuring vibrant green grass and tropical plants. A seating arrangement with a table and chairs can be seen under an overhang, framed by a flowering tree. The ocean glistens in the distance beneath a clear blue sky.

4.95 out of 5 average rating, 182 reviews

Amazing Kapalua ,Stay 7 nights, only pay for 6 !

Our place is close to 3 beautiful beaches, 2 spectacular golf courses, tennis garden, hiking trails, whales, zip line, shops, restaurants, pools, barbecue, and spas. You’ll love our place because of the incredible views from the outdoor garden. It is huge and we call it our living room on the lawn. You'll love the ambiance, neighborhood, people. You will love everything about the Ridge at Kapalua. Our place is good for couples, solo adventurers, business travelers, not suitable for children.

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A dining table is set with plates and utensils, positioned on a lush green lawn. Palm trees surround the area, offering a tropical ambiance with the ocean visible in the background under a partly cloudy sky.

4.9 out of 5 average rating, 168 reviews

OCEAN FRONT Condo at Napili Bay, Near Kapalua!

Thank you for checking out my OCEAN FRONT condo located at the Charming Napili Shores resort. This recently renovated condo is in the high demand I building, which is the closest to the ocean in the complex. Imagine every morning you enjoy the brunch ordered from the famous Gazebo restaurant at your own Lanai right beside the ocean; Soak up the sunshine on the Napili beach steps away from the resort during the day, and come back in the evening to watch the stunning sunset in your room!

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Farm stay in Haiku-Pauwela

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.

4.94 out of 5 average rating, 683 reviews

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

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An aerial view captures the lush green landscaping surrounding the property, featuring palm trees and well-maintained rolling lawns. The ocean sparkles in various shades of blue, while nearby buildings with solar panels are visible, creating a serene atmosphere just steps from the beach.

4.98 out of 5 average rating, 110 reviews

Napili Bay Oceanview Resort Hideaway

Welcome to Napili Bay, Maui's hidden gem, and a favorite spot for some of the best snorkeling on Maui. Relax in the ocean breeze from your private lanai. Enjoy ocean views throughout the condo. Lush tropical landscaping, plumerias, monkeypods, and many more plant varieties throughout the property. 2nd floor studio condo, beautiful vaulted ceilings, low density property, old school Hawaiian resort. Easy access to world-class beaches, restaurants, shopping and golfing.

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4.97 out of 5 average rating, 173 reviews

Napili Bay Studio $169 Airbnb guest’s fee included

Aloha! Corner unit . 43 vizio TV(Smart) Free WiFi 1 King size bed Ceiling fan AC 12000 BTU Balcony’s chair Beach umbrella Beach chairs (2) And cooler Oven Microwave Refrigerator Pots,pans,utensils Coffee maker Complimentary coffee Set of beach towels (2) Set of towels,hand towels Etc Hair dryer Pool/all year around Iron Start up hand soap shampoo,conditioner. Free parking Bbq area Toaster Blender Sal/pepper Ceiling fan 10 min walk to Napili bay

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Popular amenities for Kapalua family-friendly rentals

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Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A serene view captures oceanfront scenery at sunset, with vibrant sun rays filtering through palm trees. Lush green grass leads to rocky shorelines, while gentle waves crash in the background, providing a tranquil backdrop to the breathtaking coastal landscape.

4.96 out of 5 average rating, 112 reviews

Direct Oceanfront View Napili Bay Maui

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A view from the lanai features lush green grass and palm trees swaying gently in the breeze. A glimpse of the ocean is visible in the distance, with neighboring buildings set against a clear blue sky.

4.96 out of 5 average rating, 279 reviews

Ocean View Oasis at Napili, West Maui

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A modern living area showcases a large flat-screen television mounted above a white entertainment unit. A polished wooden table is centered in the room, adorned with decorative items. Potted plants add a touch of greenery, complemented by comfortable seating options and natural light from tall windows.

4.88 out of 5 average rating, 166 reviews

Luxury 3 Bedroom Island Retreat and Private HotTub

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A bright living area is furnished with a comfortable couch and a wooden coffee table. A patterned rug lies underfoot, and the space features large windows reflecting natural light. The area includes a TV and shelves with decorative items, creating a functional and inviting ambiance.

4.95 out of 5 average rating, 234 reviews

Cozy Clean Quiet 1 BD/1BA with A/C in Napili

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A spacious balcony offers a dining table set for six, with sweeping ocean views in the background. The scene is complemented by comfortable outdoor seating and lush greenery in a potted plant, all framed by the clear blue waters and sky.

4.94 out of 5 average rating, 108 reviews

Stunning Panoramic Oceanfront 2 Bed Bath with AC

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A comfortable lanai features a dining table surrounded by cushioned chairs, with an unobstructed view of the ocean and beach. Lush palm trees frame the scene, while gentle waves reflect the blue sky and distant islands.

4.94 out of 5 average rating, 169 reviews

Absolute Beachfront with Million-Dollar Views!

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4.99 out of 5 average rating, 239 reviews

A scenic view captures the sunset over a lush landscape, with a pool reflecting the colorful sky. Tall trees frame the scene, and the distant ocean is visible beneath the dramatic clouds. The vibrant greens of the surrounding vegetation provide a serene backdrop.

Cottage in Makawao

Rustic Upcountry retreat with breathtaking views!

Indoor spacesFamilyHiking

4.99 out of 5 average rating, 156 reviews

The open-concept living space features a modern kitchen with sleek cabinetry and a bar top overlooking a sunlit living area. Floor-to-ceiling windows reveal panoramic ocean views and access to a comfortable seating area, inviting relaxation in a coastal setting.

Condo in Kaanapali

Luxury Mahana 1bd/2ba-Great Views-Free Park/WiFi

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Family- and pet-friendly home rentals

Farm stay in Haiku-Pauwela

The cottage exterior is framed by lush greenery and vibrant flowers, complemented by a decorative stone pathway leading to the entrance. A unique circular window and a red door enhance the cottage's character, while balconies offer inviting views of the surrounding landscape.

4.99 out of 5 average rating, 380 reviews

Maliko Retreat

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4.93 out of 5 average rating, 416 reviews

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!

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4.89 out of 5 average rating, 569 reviews

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

FamilyKitchenHiking

4.92 out of 5 average rating, 144 reviews

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!

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4.87 out of 5 average rating, 262 reviews

An inviting bedroom features a spacious bed with a patterned blanket. Two framed paintings adorn the light blue walls, and a bedside lamp provides soft illumination. A doorway leads to a bright living area, with natural light visible from additional outdoor access.

Apartment in Wailuku

2B/2B Cottage/Cozy/Central/Private/Historic town

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Townhouse in Wailea-Makena

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.

4.97 out of 5 average rating, 145 reviews

Beautiful Wailea Ekolu Townhouse-Perfect Get-Away

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4.87 out of 5 average rating, 120 reviews

Home in Paia

Two Bedroom Green turtle House

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4.8 out of 5 average rating, 362 reviews

The kitchen area features wooden cabinets and ample counter space, with appliances including a microwave and refrigerator. A round dining table with rattan chairs is set nearby. Decorative elements and a ceiling fan enhance the inviting atmosphere, with flowers adding a touch of color.

Condo in Kihei

Across from Beach - Unit #253

KitchenIndoor spacesAir conditioning

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 21 reviews

A spacious living area is presented with a light-colored sectional sofa and a wooden coffee table. A wall-mounted television is visible, alongside a patterned armchair. Large glass doors open to the lanai, allowing natural light and views of the surrounding landscape.

Home in Kapalua

Relaxation in Kapalua-Specials!

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5.0 out of 5 average rating, 10 reviews

Amazing Ocean View-Sleeps 6-Kapalua Golf Villa 21P

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5.0 out of 5 average rating, 23 reviews

Epic Ocean View. Remodeled. Luxury condo. 2 Pools

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4.86 out of 5 average rating, 29 reviews

Villa in Kapalua

Oceanfront Kapalua Bay Villa 23G1 Gated Coastal El

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A furnished lanai features a round glass dining table surrounded by four metal chairs, offering expansive views of the Pacific Ocean and greenery. The sky is bright with clouds, enhancing the serene outdoor space ideal for relaxation.

4.97 out of 5 average rating, 29 reviews

Experience Unmatched Comfort with Magnificent Pano

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5.0 out of 5 average rating, 6 reviews

An expansive outdoor lanai offers sweeping ocean views under a partly cloudy sky. Several black wicker chairs are positioned along the railing, inviting relaxation while overlooking the rocky shoreline and vibrant blue water.

Apartment in Kapalua

Kapalua Bay Villa 34B2 By Parrish Maui

KitchenFamilyBeach

The image displays a bright room with large floor-to-ceiling windows offering views of the open lawn and the ocean. A comfortable armchair is positioned near a small wooden side table. Lush greenery is visible outside, enhancing the scenic atmosphere.

4.74 out of 5 average rating, 23 reviews

Kapalua Bay Villa 38G3 - Private OV Maui Escape

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A covered outdoor dining area showcases a spacious table set for four. Lush tropical landscaping and palm trees frame the view of the ocean and pool area. The tranquility of the setting is highlighted by bright blue skies and the gentle shoreline in the distance.