Family-friendly holiday rentals in Kaanapali

A living room space features a patterned couch and a wooden coffee table. A dining area with wooden chairs is visible beside a balcony door leading to ocean views. Large glass windows create an open atmosphere, allowing natural light to fill the room.

4.94 out of 5 average rating, 132 reviews

Oceanfront Two Bedroom at Kaanapali Shores #504

Enjoy oceanfront views from this 5th floor 2-bedroom / 2-bath condo at the popular Kaanapali Shores Resort. Central A/C, spacious living room, washer/dryer, full kitchen, wifi, cable tv & SNES classic Just steps away from the ocean Watch beautiful sunsets from the resort The resort has pools, hot tubs, restaurant and bar, and more Supermarket across the street *Wildfire Update* This condo is located in North Kaanapali outside the Lahaina wildfire burn zone. West Maui is now open to visitors

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, 139 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 & centrally located next to the Montage Resort. 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, shopping, spas, & several bays/beaches great for snorkeling, surfing, & relaxing, this is the perfect home base.

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.

4.99 out of 5 average rating, 135 reviews

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

Locally Owned and Operated 1BD/2BA condo with the best direct beachfront location, panoramic Ocean views, sunsets, and seasonal whale watching. The owner’s spared no expense in renovating this unit making it hand’s down one of the nicest units in all of the Mahana. Wake up to the cool tropical breeze and sounds of the shoreline just 50 feet away. Floor to ceiling windows in the living area and bedroom bring the stunning views and warm Maui sun inside while central AC keeps you cool inside.

4.99 out of 5 average rating, 202 reviews

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.

Bungalow in Lahaina

Ka Hale Aloha (The 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 than ever before!! 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, just steps from the ocean. This is a unique experience...there’s nothing quite like "Ka Hale Aloha" on island * Check us out on IG at @kahalealoha

A welcoming studio space features a king bed and comfortable seating area. A round dining table with chairs and a wooden coffee table are positioned beside the large window, which offers views of the outdoor landscape. Artwork adorns the walls, adding a touch of style.

4.95 out of 5 average rating, 179 reviews

Ocean Tropics Oasis, Beachfront, King bed, AC/pool

Welcome to the Royal Kahana! Views from your private lanai are first class. View includes ocean, sunset, neighboring islands, mountains, and even humpback whale breaches. Relax at our upgraded studio which has all the amenities you need for an amazing stay. Recent upgrades include updated lighting, artwork, furniture, all new bedding and pillows, new and additional seating on the lanai, and OLED tv. USB ports by bed and kitchen. Great for couples, with sofa bed we can accommodate 3.

Superhost

The resort's large oasis pool is surrounded by lush tropical landscaping, featuring palm trees and vibrant flora. Comfortable lounge chairs and umbrellas are positioned around the pool area, while several guests enjoy the serene water. The four-story buildings create a welcoming atmosphere against a bright blue sky.

4.82 out of 5 average rating, 124 reviews

Kaanapali Shores Modern Beachside Resort Condo

Located on Kaanapali Beach, Kaanapali Shores is a full service resort offering amenities that surpass other resorts. Lavish tropical landscaping, waterfalls, large oasis pool and lap pool at the ocean edge, 2 hot tubs, sauna, ocean activities center, retail stores, Fitness Center, Pickle Ball Court and other great amenities. The on-site Beach Club Restaurant offers ocean views live music and a great Happy Hour! Unit 538 has substantial upgrades compared to other units in the resort.

4.94 out of 5 average rating, 140 reviews

Kaanapali Fairway Vista - Legal STR Hotel Zoned

Escape to a Slice of Paradise – Where the Fairway Meets the Ocean. This beautifully appointed condo offers the best of Kaanapali living, featuring a prime golf course front position with serene, sweeping views and a sparkling partial ocean view that will take your breath away. Wake up to the sight of golfers setting off on the world-renowned Kaanapali Golf Courses. In the afternoon, relax on your private lanai and watch the sunset paint the Pacific Ocean in hues of gold and orange.

The image captures a vibrant pool surrounded by natural stone features and lush tropical landscaping. The resort's multi-story buildings are visible in the background, framed by swaying palm trees under a partly cloudy sky. A wooden bridge crosses the pool area, adding to the serene atmosphere.

4.99 out of 5 average rating, 162 reviews

Beautiful Ocean View on Quiet Side of Honua Kai!

*** NO RESORT OR PARKING FEES! *** Honua Kai is a Four Star resort with four pools, five spas, a fitness center, Aina Gourmet Market, and beachfront Dukes Restaurant on premises. Our one bedroom condo has a partial ocean view from the lanai, has a KING sized bed in the bedroom AND queen SOFA SLEEPER for additional guests. We stock our condo with four beach chairs, umbrella, two coolers, boogie boards, and pool toys for you to use.

4.96 out of 5 average rating, 441 reviews

A welcoming living area features a comfortable sectional sofa beside a modern coffee table, with natural light filtering through large windows. An outdoor patio is visible, with an umbrella-shaded table and chairs overlooking lush tropical gardens and ocean views.

Home in Wailea

Stunning ocean view, heated pool at home by Wailea

Ocean, sunset views, unique home reminiscent of a Victorian villa with heated private pool for guests in the villa, tropical gardens. Home renovated and maintained by designer. Cal King in main, second has twin beds. Pac n play and high chair are available. Open plan living with dining and relaxing on the lanai. Keawakapu beach, Wailea shops and restaurants 5 minutes drive. Your private view retreat. #BBMK 2016/0003

4.96 out of 5 average rating, 145 reviews

The residence features a striking facade with dramatic floor-to-ceiling windows. Surrounded by lush greenery, the exterior is enhanced by modern architectural lines and a welcoming entrance, leading to spacious parking areas and steps that guide guests into the home.

Townhouse in Lahaina

#1 Guest Favorite for Napili & Kapalua Bays!

Enjoy this luxury residence with beautiful bamboo flooring, contemporary island design, and dramatic floor-to-ceiling windows. Staying here means you're only a few steps away to heavenly Napili & Kapalua Bays. This is not just any condo, it's your special Maui retreat. Come see for yourself, a must do for all travelers with the desire for easy access to a famous beach and the exclusive Kapalua lifestyle.

A fully equipped kitchen features granite countertops, a refrigerator, microwave, and stove with an oven. Two wooden bar stools are positioned at the counter. The open layout allows for easy movement between the kitchen and living areas.

4.98 out of 5 average rating, 191 reviews

Kaanapali Shores - SUPER CLEAN! OceanView 1bd/1ba

A legal short term rental! 1 bedroom, 1 bath with open floor plan. This condominium has a comfortable Cal-King bed in the bedroom and sofa sleeper in the living-room. **Central A/C*Fully equipped kitchen w/ granite counters*refrigerator*stove top + oven*coffee maker* microwave* dishwasher* washer/dryer* Free in room WiFi** Onsite gym is managed by an outside contractor and charges $9/day for useage.

An outdoor lanai features a small table and two wicker chairs, offering a direct view of the expansive Pacific Ocean. The ocean's vibrant blue waters stretch toward the horizon under a partly cloudy sky, creating a serene and inviting area for relaxation.

4.98 out of 5 average rating, 198 reviews

DIRECT OCEAN FRONT STUDIO W OCEAN IS UR BACK YARD!

This is a hotel-zoned condo. It will not be affected by potential upcoming county regulations. Book with confidence!! Thank you for considering my direct ocean front studio condo in Kahana, my condo is located minutes outside of Lahaina , Kaanapali , Napili and Kapalua. You'll find the ocean view from my lanai/ room to be breathtaking and serene. This is truly an hidden gem on Maui.

Popular amenities for Kaanapali family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A vibrant cultural performance takes place on an outdoor stage. Performers in traditional attire, featuring skirts made from green leaves and floral necklaces, are seen dancing with wooden sticks. The backdrop is enhanced by tiki torches, creating an immersive atmosphere.

4.94 out of 5 average rating, 191 reviews

Eldorado Beach Resort Ka'anapali - Whalers Village

A tranquil pool area is surrounded by lush tropical vegetation, with a mix of vibrant flowers and palm trees. Relaxing lounge chairs are positioned near the water, offering scenic views of distant mountains and the ocean. The sky is clear, enhancing the inviting atmosphere.

4.87 out of 5 average rating, 182 reviews

Crazy Good Deal MKV Resort Ka'anapali - Ocean View

A spacious living area features a comfortable sofa adorned with decorative pillows. A light-colored coffee table is positioned centrally on a patterned rug. The open kitchen is visible in the background, equipped with modern appliances and sleek cabinetry. Bar stools line the kitchen counter.

4.97 out of 5 average rating, 143 reviews

Beautiful Papakea 1 Bedroom with A/C

A spacious bedroom is equipped with a large bed adorned with colorful pillows. Two patterned armchairs are positioned beside a small table, creating a cozy seating area. A glass sliding door provides natural light and offers a view of the outdoor greenery.

4.98 out of 5 average rating, 99 reviews

Your Oasis by the Sea, stay at B103!

4.95 out of 5 average rating, 131 reviews

An open-concept living area features a spacious dining table with blue upholstered chairs, complemented by a calming color palette. The kitchen, equipped with modern appliances, is visible in the background, while natural light fills the space through large windows.

Apartment in Wailea

MAUI BLISS! RARE Wailea 3-bedroom...sleeps 10!

4.97 out of 5 average rating, 125 reviews

Ocean's Edge Romance: Sunsets, Whales, Views!

4.87 out of 5 average rating, 232 reviews

A view from a balcony captures a lush, green landscape dotted with palm trees. A pool is nestled amongst manicured lawns, with gentle ocean waves visible in the background under a partly cloudy sky.

Flat in Lahaina

Beautiful, Remodeled Ocean View Condo

The living area features a rattan furniture set, including a sofa adorned with tropical print cushions. A glass coffee table rests on tiled flooring, while large glass doors provide views of the lush garden outside. A ceiling fan adds to the open, airy ambiance.

4.91 out of 5 average rating, 162 reviews

Affordable Gem Honokowai /NEW AC/Location! Unit 2

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 116 reviews

The exterior of a spacious home is framed by lush tropical plants and trees. A charming pathway leads to a welcoming front deck illuminated by soft lighting. Large sliding doors enhance visibility into the interior, where comfortable seating is visible in a cozy living space.

Home in Wailea

Mana Hale Vacation Rental

4.97 out of 5 average rating, 128 reviews

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

4.89 out of 5 average rating, 503 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

4.85 out of 5 average rating, 129 reviews

Apartment in Kihei

Updated 2-Bed Studio- Steps from the Beach/Shops

The image captures a serene beach scene with clear turquoise waters gently lapping against a sandy shore. Distant islands are visible on the horizon under a bright blue sky adorned with soft white clouds. The tranquil ocean setting suggests opportunities for swimming and snorkeling.

4.85 out of 5 average rating, 124 reviews

A jewel on Oceanfront & Breath Taking Views.

4.93 out of 5 average rating, 370 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!

4.88 out of 5 average rating, 251 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.

Flat in Wailuku

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

4.97 out of 5 average rating, 304 reviews

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

Ocean View - Private Cabin

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 39 reviews

A spacious living room features a sectional sofa and an accent chair with a vibrant pattern, complemented by a round coffee table. Large glass doors open to a water-view lanai, allowing natural light to fill the space. Contemporary art adds visual interest to the neutral walls.

Home in Lahaina

Mahalo Pono @ Ka'anapali Royal

Superhost

5 out of 5 average rating, 4 reviews

Maui Beach Frt Condo w/ AC Kaanapali Shores Resort

5 out of 5 average rating, 45 reviews

A dining table is set for breakfast on the lanai, featuring colorful flowers in a vase and plates with food. The ocean can be seen in the background, along with distant islands and a clear blue sky, creating a serene beachfront setting.

Flat in Lahaina

Oceanfront penthouse - stunning view!

A tranquil pool area is framed by palm trees and tropical landscaping. Soft sunlight reflects off the clear water, while lounge chairs with shaded umbrellas are positioned around the pool, inviting relaxation. Rock formations enhance the natural beauty of the resort's outdoor space.

4.89 out of 5 average rating, 54 reviews

Westin Kaanapali Resort North Studio Villa

The outdoor pool area is illuminated by ambient lighting, surrounded by palm trees and lush landscaping. Lounge chairs are positioned around the pool, creating an inviting space. In the background, the ocean glimmers under a twilight sky, enhancing the serene atmosphere.

4.97 out of 5 average rating, 37 reviews

Huge Luxury Condo | partial Ocean View on Beach

A view from the lanai showcases the ocean with varying shades of blue extending toward the horizon, framed by lush palm trees. A clear sky enhances the serene atmosphere, creating a peaceful setting for relaxation.

5 out of 5 average rating, 6 reviews

HONUA KAI Largest 1bd Ocean View Closest to Ocean!

A warm sunset illuminates the sky over the ocean, viewed from a cozy lanai. A wooden table is set with two glasses and a bottle, accompanied by two chairs featuring soft cushions. Lush greenery can be seen in the distance, blending with the scenic backdrop.

4.98 out of 5 average rating, 116 reviews

Spectacular Ocean Views, 1st Class, Luxury Condo

An outdoor dining area is presented on a private lanai, featuring a table set with two glasses and plates of food. In the background, palm trees sway against a clear blue sky, overlooking stunning ocean views that include distant islands.