Family-friendly holiday rentals in Kaanapali

A lanai offers a view of the ocean, framed by tall palm trees swaying in the breeze. In the foreground, a small table is set with two wine glasses, inviting relaxation and enjoyment of the coastal scenery.

4.88 out of 5 average rating, 321 reviews

Kaanapali Shores Double Oceanview Resort Living

It gets no better than world class Kaanapali Beach! Add our gorgeous yet sensibly priced condo great for singles, up to 3 couples and perfect for families saving the high cost of 2 bedroom units! We are hotel zoned in a beautiful resort, not being barred from short term rental. Wake to ocean views from the king bed and from the living room and lanai (balcony). Enjoy resort amenities with no resort fee! You're beach ready with included beach umbrella, chairs, boogie boards, cooler and toys!

4.99 out of 5 average rating, 168 reviews

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.

Condo in Kapalua

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.

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, 160 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.

4.93 out of 5 average rating, 151 reviews

Cottage in Kaanapali

Kaanapali Cottage ICC 29 Indoor/Outdoor Living

International Colony Club’s cottage 29 is located in the world-famous Kaanapali Beach area, and a five minute walk from one of Maui’s best beaches. Built in 1964, this community affords a spacious and mature landscape between 44 private cottages spread over 10 acres. Our Hawaiian plantation style cottage is reminiscent of homes built during the plantation era and conveniently located close to beaches, shopping and restaurants, but is secluded from the hustle and bustle of the big resorts.

Apartment in Napili-Honokowai

A spacious balcony features a simple dining table surrounded by two chairs, offering an unobstructed view of the ocean. Palm trees frame the scene, while a bottle and glass sit on the table, reflecting the bright blue sky above and the serene water below.

Maui Full Oceanfront Paradise

Indulge in the ultimate Maui getaway at our full oceanfront condo. The cozy balcony beckons you to unwind and marvel at the mesmerizing sea life. Sip on your morning coffee, or relish a sunset cocktail while you watch the ocean's playful inhabitants. For those warm tropical nights, rest easy knowing that the condo is equipped with air conditioning to ensure a comfortable night's sleep. The fully stocked kitchen provides all the essentials for cooking up a delightful island feast.

4.97 out of 5 average rating, 107 reviews

4.95 out of 5 average rating, 157 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.

4.99 out of 5 average rating, 185 reviews

Quiet Luxury Awaits: Partial Ocean-View Gem

Experience luxury at Honua Kai with ZERO resort or parking fees! This FIFTH floor 1-bedroom retreat features a partial ocean view from the lanai, a plush King bed, and a Queen sofa sleeper. Enjoy premium resort amenities including four pools, five spas, and beachfront dining at Duke’s. We provide all your beach essentials—chairs, an umbrella, coolers, and boogie boards! Plus, stay connected with Gig-speed Wi-Fi, perfect for remote workers. Your ultimate getaway awaits!

The resort pool is illuminated at dusk, surrounded by lush palm trees and landscaped greenery. Lounge chairs are positioned along the water's edge, with torches casting a warm glow. The ocean can be seen in the distance, creating a tranquil atmosphere.

4.94 out of 5 average rating, 101 reviews

Luxury 2 BD Condo at Honua Kai Resort on the Beach

2 - TWO BEDROOM & 1 Bath! It is 915 sq. ft facing the park. with a 175 sq ft lanai. Nana wall of windows opens up this living space to feel like your inside is outside when enjoying this beautiful condo. This has a gourmet kitchen is fully stocked & featuring beautiful stainless steel appliances and french door fridge. The Master bedroom has a king-size bed plus an 4K Smart TV, and a huge ensuite bath. High-end sound bar in the living room.

4.98 out of 5 average rating, 207 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.

A spacious lanai offers a stunning ocean view, featuring a glass-top table with two wicker chairs. Bright blue beverages are placed on the table, while blue skies and gentle waves stretch out towards the horizon.

4.98 out of 5 average rating, 140 reviews

Stylish Love Hideaway, Maui Kaanapali Oceanfront

Oceanfront studio in one of a kind boutique condominium, on world famous Kaanapali Beach. Wake up to a breathtaking oceanview, take it all in from spacious lanai, fall asleep to the sound of the ocean every night Located on the 3rd floor with close touch to ocean breeze and fantastic views, easy access to world-class beaches, restaurants, shopping and golfing

4.81 out of 5 average rating, 118 reviews

A spacious outdoor area features a private pool with clear blue water, framed by stone landscaping. An arched structure offers shade near the pool, and a red bowl sculpture adds a pop of color. Lush greenery surrounds the space, enhancing the serene environment.

Villa in Kaanapali

Kaanapali Fairway Villa 3BR/3BA.

Welcome to this Kaanapali Golf course 3 bedroom 3 bath bed and breakfast. Permit number BBWMT 2021/0003-159 Halelo. This beautiful Mediterranean home is conveniently located on hole number 5 of the Kaanapali Golf Course with a private pool, swim up bar, and ocean view. Recently renovated with many added amenities and features, please see in description below.

4.84 out of 5 average rating, 159 reviews

Gorgeous 2bed/2bath Papakea Oceanview!

Our spacious, remodeled two bedroom/two bathroom condo on the 4th floor is fully air conditioned with separate AC controls in each room. With its vaulted ceilings and a gorgeous ocean view from a roomy lanai, this is the perfect home base for up to 6 people to relax and enjoy all that Maui has to offer. Everything you need to enjoy your vacation is provided.

Popular amenities for Kaanapali family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A dining setup is presented on a patio table with bowls and turquoise glasses. A decorative pineapple stands at the center. The background features a stunning ocean view with clear blue waters and a line of greenery, under a bright sky with soft clouds.

4.97 out of 5 average rating, 130 reviews

Mahana at Kaanapali- Beachfront Walkout Jewel

Lush tropical gardens and palm trees are visible alongside a well-manicured lawn. A blue ocean stretches into the distance under a partly cloudy sky. In the foreground, a swimming pool area features lounge chairs, while a community building can be seen to the left.

4.88 out of 5 average rating, 140 reviews

Condo in Lahaina, New Remodel, Amazingly Peaceful

4.93 out of 5 average rating, 213 reviews

Eldorado Beach Resort Ka’anapali - Whalers Village

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, 150 reviews

Beautiful Papakea 1 Bedroom with A/C

4.93 out of 5 average rating, 121 reviews

Kaanapali Shores Resort Studio #334 ~ West Maui ~

4.94 out of 5 average rating, 31 reviews

Ocean View Kaanapali Shores Condo | Pool & Beach

5.0 out of 5 average rating, 3 reviews

Honua Kai - Konea 510

4.96 out of 5 average rating, 55 reviews

2BR/2BA | @ Alii Beachfront Resort | Sleeps 8

Family- and pet-friendly home rentals

4.84 out of 5 average rating, 433 reviews

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

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.

Maliko Retreat

4.99 out of 5 average rating, 387 reviews

4.89 out of 5 average rating, 576 reviews

Guest suite in Wailuku

Oceanview, Banana Bread, Hot Tub & Sauna near OGG

4.93 out of 5 average rating, 423 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!

4.86 out of 5 average rating, 108 reviews

Condo in Kihei

Sleeps 8 Ocean View 3bth Kamaole Beach HOT TUB

4.96 out of 5 average rating, 146 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

4.95 out of 5 average rating, 115 reviews

A private lanai features a round glass-top table surrounded by colorful cushioned chairs. Lush tropical plants and palm trees create a serene garden view, while a clear blue sky adds brightness to the scene.

Condo in Kihei

Walk to Kam Beach! King Bed, Pools, Pet Friendly.

4.82 out of 5 average rating, 114 reviews

Home in Wailuku

3B2B w/HotTub FamilyComfort HawaiianaCharm Central

Family-friendly home rentals with a pool

The lanai offers a table with a blue glass bottle as its centerpiece, surrounded by two comfortable chairs. Vibrant blue surfboards are positioned against the wall, while the ocean gently laps at the shore in the background, framed by swaying palm trees.

4.96 out of 5 average rating, 281 reviews

Soothing Waves with 180° View In Kahana, HI

A private lanai features a round glass table surrounded by two rattan chairs. Lush tropical plants are positioned in pots around the area. The ocean stretches into the distance, framed by majestic mountains under a clear blue sky.

4.97 out of 5 average rating, 244 reviews

Kaimana On top of the Ocean Hideaway MermaidPalace

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.

Peaceful Maui Bungalow | Ka Hale Aloha-Love Shack

4.99 out of 5 average rating, 223 reviews

A vibrant resort pool is visible, featuring clear blue water and surrounded by lush tropical palm trees. Several lounge chairs are positioned around the pool, with bright red umbrellas providing shade. In the background, the ocean can be seen beyond the landscaped grounds.

4.64 out of 5 average rating, 22 reviews

Honua Kai Resort & Spa Partial Ocean View 2BD/2BA

5.0 out of 5 average rating, 4 reviews

Luxury 2BR Penthouse with Breathtaking Ocean Views

5.0 out of 5 average rating, 22 reviews

Oceanfront Mahana Panoramic Pacific Views

Apartment in Napili-Honokowai

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.

Oceanfront penthouse - stunning view!

5.0 out of 5 average rating, 80 reviews