Family-friendly vacation rentals in Kaanapali

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

Maui Gov’t Approved Short Term Rental - Hotel District- Direct beach access with ground floor spacious lanai. Unreal views from this one bedroom, one sofa bed ground level entry, beachfront condo located directly on Kaanapali Beach. Central AC with LR and BR providing separate direct walkout to the lanai and 15 steps away is the beach! 75" TV, Sonos system, Apple TV, washer/dryer etc. Stocked kitchen includes coffee makers and supplies to get yourself ready for romantic dinners with the sunset!

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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!

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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.

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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.

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4.93 out of 5 average rating, 152 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.

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A balcony setting is presented with a round table surrounded by four high-back chairs. Two glasses filled with a red beverage sit on the table. Beyond, lush greenery and palm trees are visible, alongside a view of the ocean and resort buildings.

4.88 out of 5 average rating, 170 reviews

Newly Relisted! Discounted rates. No resort fees

We are returning our condo to Airbnb after a year and a half hosting a lovely family who’s home burned down in the Lahaina fire. They have a new permanent home and are doing well so we are happy to have our Airbnb. guests back! This third-floor oceanview condo has a beautifully remodeled and fully equipped kitchen with granite countertops, marble backsplash and stainless steel appliances. Living room A/C. The bathroom has been remodeled with a granite countertop and walk-in shower.

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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.

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4.97 out of 5 average rating, 107 reviews

4.95 out of 5 average rating, 158 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.

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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

Valley Isle Resort 306 We are located beachfront with an amazing view of the ocean and sunset. We can look right down into the water and watch the turtles swimming. We offer a full kitchen including poolside barbecue grills. Within a block of our Resort are several restaurants and bars. Our condo has a comfy queen-size wall bed along with a small sofa bed. We offer a well stocked kitchen. The ambiance is soothing and relaxing. Our place is good for couples and solo adventurers.

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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!

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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.

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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

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Popular amenities for Kaanapali family-friendly rentals

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Free parking on premises

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Family-friendly home rentals with air conditioning

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

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Vacation home in Napili-Honokowai

The living area showcases large floor-to-ceiling windows framing ocean views. A comfortable sectional sofa is positioned around a wooden coffee table, with a wall-mounted TV and a rustic cabinet nearby. A ceiling fan adds a cooling touch, and outdoor seating is visible through the glass doors.

Oceanfront Paradise! Sea Turtle Cove C24 Napili Pt

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4.97 out of 5 average rating, 136 reviews

Vacation home in Napili-Honokowai

Sun loungers are arranged on a grassy area next to the water, with palm trees swaying in the light breeze. The ocean is visible in the background, with distant mountains on the horizon. The sky is partly cloudy, creating a peaceful atmosphere.

Marvelous Maui, Oceanfront Paradise!

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4.96 out of 5 average rating, 103 reviews

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

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4.93 out of 5 average rating, 213 reviews

Eldorado Beach Resort Ka’anapali - Whalers Village

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A spacious studio features a large bed with crisp white linens, complemented by soft throw pillows. Mirrors enhance the light throughout the room. A comfortable seating area with a light-toned sofa is present, while floor-to-ceiling windows offer sweeping views of the Pacific Ocean.

4.98 out of 5 average rating, 105 reviews

Maui Penthouse Studio Mahana 1213

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4.98 out of 5 average rating, 252 reviews

On Top of Water View-5 Stars-Pohailani 303

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4.96 out of 5 average rating, 153 reviews

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

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Family-friendly home rentals with a pool

4.79 out of 5 average rating, 112 reviews

2 BdRm - Cozy Condo near Kaanapali! B5

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4.96 out of 5 average rating, 55 reviews

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

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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

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5.0 out of 5 average rating, 22 reviews

Oceanfront Mahana Panoramic Pacific Views

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5.0 out of 5 average rating, 14 reviews

Oceanview Kaanapali Shores- Beachfront resort w/AC

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5.0 out of 5 average rating, 29 reviews

Beachfront Ka'anapali Studio - Vacation West Maui

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4.96 out of 5 average rating, 24 reviews

Newest 1 BR, Modern Coastal Luxury, Beachfront Cab

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5.0 out of 5 average rating, 3 reviews

Ocean View steps from beach, dining, shopping 723

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Family-friendly home rentals with a kitchen

4.96 out of 5 average rating, 26 reviews

Honua Kai K830 - Renovated Tranquil Mountain Views

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4.94 out of 5 average rating, 32 reviews

Walk to Kaanapali Beach! Fully Remodeled 1BR, Pool

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5.0 out of 5 average rating, 9 reviews

Direct Beachfront 1BD Escape w AC - MKV 179

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4.73 out of 5 average rating, 41 reviews

The Perfect Spot for Your Dream Vacation!

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5.0 out of 5 average rating, 4 reviews

Luxury 2BR Penthouse with Breathtaking Ocean Views

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A bright living area is visible, featuring a comfortable couch and dining space that opens to a lush outdoor garden. Large sliding glass doors allow natural light to fill the room, and decorative accents can be seen on the counters and furniture, inviting a relaxed ambiance.

4.88 out of 5 average rating, 95 reviews

Honua Kai Desired ground floor. Suite H116

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An aerial view captures the resort unit in proximity to the Kaanapali golf course and the coastline. Lush green lawns and palm trees frame the landscape, with the ocean visible in the distance. The serene environment highlights the proximity to both the beach and recreational areas.

4.95 out of 5 average rating, 78 reviews

Maui Eldorado J102 - Black Rock and Ocean Views

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