Family-friendly holiday rentals in Kaanapali

4.97 out of 5 average rating, 128 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!

Indoor spacesFamilyQuiet

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!

KitchenIndoor spacesCleanliness

4.99 out of 5 average rating, 166 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.

FamilyIndoor spacesShared spaces

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.

FamilyIndoor spacesQuiet

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.

KitchenIndoor spacesBathroom

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.

FamilyIndoor spacesWalkability

4.95 out of 5 average rating, 156 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.

Indoor spacesKitchenSleep quality

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.

KitchenFamilyTV

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, 138 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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4.8 out of 5 average rating, 116 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.

Indoor spacesKitchenParking

4.84 out of 5 average rating, 158 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.

FamilyKitchenNearby

A well-lit living area features a comfortable seating arrangement, including a sofa and two armchairs. Natural light filters in through large sliding glass doors, leading to a shaded lanai with views of greenery. Decorative pillows add subtle color to the neutral tones of the space.

4.87 out of 5 average rating, 114 reviews

Honua Kai, K240 - House of the Quiet Shade

No hidden fees in price! You pay the base rate, the housekeeping fee, an Airbnb guest fee and that’s all. Honua Kai. Konea 240. On the shady and quiet side of the building. King bed in the master, queen in the den and a queen sofa bed with a memory foam mattress. Second floor unit. Don't wait forever for the busy elevators-- take the stairs right up.

KitchenIndoor spacesWi-Fi

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

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

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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, 184 reviews

Quiet Luxury Awaits: Partial Ocean-View Gem

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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

FamilyIndoor spacesCheck-in

4.91 out of 5 average rating, 169 reviews

Oceanfront Condo at Napili Bay | Newly Refreshed

KitchenIndoor spacesAmenities

4.94 out of 5 average rating, 148 reviews

Condo in Lahaina

Beachfront Resort, Peaceful Mountain View Studio

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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

FamilyIndoor spacesComfort

A colorful rainbow arches across the sky, visible through expansive glass doors. The view extends over a serene landscape, framed by a spacious private lanai with outdoor seating. Light clouds add depth to the picturesque backdrop of the West Maui mountains.

4.94 out of 5 average rating, 121 reviews

HUGE 1 Bdrm Penthouse @ luxurious Honua Kai Resort

FamilyKitchenComfort

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

Indoor spacesKitchenLayout

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 421 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!

KitchenIndoor spacesCondition

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, 387 reviews

Maliko Retreat

Indoor spacesFamilyHiking

4.86 out of 5 average rating, 108 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 spacesAir conditioning

4.89 out of 5 average rating, 571 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

Indoor spacesKitchenPool

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

KitchenFamilyLayout

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

Indoor spacesKitchenLocation

4.82 out of 5 average rating, 114 reviews

Home in Wailuku

3B2B w/HotTub FamilyComfort HawaiianaCharm Central

Indoor spacesFamilyOutdoor spaces

4.87 out of 5 average rating, 120 reviews

Home in Paia

Two Bedroom Green turtle House

KitchenFamilyBarbecue

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

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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 spacesFamilySleep quality

5.0 out of 5 average rating, 3 reviews

Apartment in Kaanapali

Honua Kai - Konea 510

Value

4.93 out of 5 average rating, 30 reviews

Ocean View Kaanapali Shores Condo | Pool & Beach

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A tranquil infinity pool with shimmering blue water is situated amidst lush tropical landscaping. Towering palm trees provide shade, while vibrant greenery surrounds a shaded cabana area. The resort buildings rise in the background against a clear blue sky, offering a serene vacation atmosphere.

5.0 out of 5 average rating, 20 reviews

Gorgeous Honua Kai GREAT ViEWS & REVIEWs 2bd/2bath

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4.94 out of 5 average rating, 32 reviews

Walk to Kaanapali Beach! Fully Remodeled 1BR, Pool

KitchenFamilyAccess

5.0 out of 5 average rating, 9 reviews

Direct Beachfront 1BD Escape w AC - MKV 179

Indoor spacesFamilyAccess