Family-friendly holiday rentals in Kaanapali

4.97 out of 5 average rating, 127 reviews

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.

Apartment in Kaanapali

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!

KitchenIndoor spacesBarbecue

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.

4.87 out of 5 average rating, 319 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!

Indoor spacesKitchenHot tub

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, 159 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.

Indoor spacesKitchenTV

4.93 out of 5 average rating, 150 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.

KitchenFamilyWi-Fi

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.

4.97 out of 5 average rating, 105 reviews

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.

FamilyKitchenParks

4.95 out of 5 average rating, 155 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.

KitchenIndoor spacesOutdoor spaces

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, 279 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.

Indoor spacesFamilyNearby

The image captures a scenic view of a resort featuring natural rock formations and cascading waterfalls, surrounded by lush greenery. The buildings rise in the background, showcasing modern architecture. Sunlight illuminates the water, creating a serene and inviting atmosphere.

4.99 out of 5 average rating, 183 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!

FamilyIndoor spacesWalkability

4.94 out of 5 average rating, 147 reviews

Condo in Lahaina

Beachfront Resort, Peaceful Mountain View Studio

Come stay at Lahaina Shores 506: - Oceanfront Building: Direct access to a sandy beach, pool, and hot tub just steps from the lobby - Mountain Views: Wake up to stunning sunrises from your 5th-floor lanai - Sunny & Clear: West Maui averages ~290 sunny days/year! - Amenities Nearby: Minutes drive to open spots like the Cannery Mall, Lahaina Gateway Center, & classic restaurants - West Maui: Only ~35 mins from the airport Note: Car recommended to explore the island

FamilyIndoor spacesValue

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.

KitchenFamilyHot tub

4.98 out of 5 average rating, 206 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.

FamilyKitchenLaundry

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, 137 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

KitchenFamilyAir conditioning

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 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, 171 reviews

Absolute Beachfront with Million-Dollar Views!

KitchenFamilyGetting around

A serene landscape features a tranquil pond surrounded by lush greenery and tropical plants. The setting is enhanced by Tiki torches casting a warm glow, with palm trees framing a colorful sunset over the ocean.

4.97 out of 5 average rating, 149 reviews

Oceanfront resort, Updated condo, Air Conditioned

FamilyIndoor spacesLocation

4.91 out of 5 average rating, 169 reviews

Oceanfront Condo at Napili Bay | Newly Refreshed

KitchenFamilyAccess

4.93 out of 5 average rating, 212 reviews

Eldorado Beach Resort Ka’anapali - Whalers Village

KitchenFamilyAccuracy

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.

4.95 out of 5 average rating, 171 reviews

Oceanfront Two Bedroom at Kaanapali Shores #504

Indoor spacesKitchenLong stay

Superhost

The resort property is spread across a lush landscape with well-maintained grounds and palm trees. The two main buildings are visible, alongside several outdoor lounge areas and a swimming pool, all situated close to the sandy beach and ocean.

4.86 out of 5 average rating, 105 reviews

Kaanapali Shores Studio with Pool, Beach and AC

FamilyKitchenWalkability

4.83 out of 5 average rating, 149 reviews

Kaanapali Shores Modern Beachside Resort Condo

FamilyIndoor spacesWalkability

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, 139 reviews

Condo in Lahaina, New Remodel, Amazingly Peaceful

KitchenIndoor spacesBathroom

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 420 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!

KitchenFamilyComfort

Farm stay in Haiku-Pauwela

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.

4.97 out of 5 average rating, 332 reviews

Ocean View - Private Cabin

FamilyIndoor spacesValue

4.86 out of 5 average rating, 107 reviews

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

KitchenIndoor spacesCheck-in

4.84 out of 5 average rating, 431 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

Indoor spacesFamilyBreakfast

4.89 out of 5 average rating, 570 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

FamilyKitchenBathroom

4.97 out of 5 average rating, 145 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

FamilyKitchenAccuracy

4.95 out of 5 average rating, 114 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.

FamilyKitchenSleep quality

4.92 out of 5 average rating, 146 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!

FamilyKitchenSleep quality

Family-friendly home rentals with a pool

4.83 out of 5 average rating, 121 reviews

Lovely 1 bedroom condo across from the beach

FamilyIndoor spacesSolo travel

4.99 out of 5 average rating, 165 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

FamilyIndoor spacesBeach

A small outdoor dining set is positioned on a private lanai, featuring a round table flanked by two cushioned chairs. The backdrop showcases expansive views of the turquoise ocean and a clear blue sky, with gentle waves visible in the distance.

4.89 out of 5 average rating, 103 reviews

Rare 2 King Suites•Oceanfront•Watch Whales&Turtles

Indoor spacesFamilyLaundry

Two figures are seen wading in the clear, turquoise waters, with gentle waves lapping around them. The vibrant colors of the water showcase a gradient from shallow sandy tones to deeper blue hues, while distant islands are visible on the horizon under a clear sky.

4.94 out of 5 average rating, 102 reviews

Spectacular Oceanfront Gem!

KitchenFamilyCondition

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, 223 reviews

Peaceful Maui Bungalow | Ka Hale Aloha-Love Shack

FamilyIndoor spacesBarbecue

4.93 out of 5 average rating, 29 reviews

Ocean View Kaanapali Shores Condo | Pool & Beach

FamilyKitchenLaundry

4.94 out of 5 average rating, 32 reviews

Walk to Kaanapali Beach! Fully Remodeled 1BR, Pool

FamilyKitchenDecor

Superhost

A bright interior space features a spacious bed adorned with decorative pillows, positioned beside large floor-to-ceiling windows offering sweeping ocean views. A dining table with two chairs is set near the window, complemented by a painting of tropical foliage on the wall.