Family-friendly holiday rentals in Kaanapali

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, 143 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, 139 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, 205 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 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, 189 reviews

MKV Beach Resort Ka'anapali - Ocean & Sunset Views

Note... MKV resort charges $35 per day due at check in. Beautifully updated spacious studio with ocean view. Amazing sunsets and whale watching are found here. Features new modern furniture, fresh paint and new decor throughout. MKV has direct beach access, two swimming pools, hot tubs, spa, gym, shuffleboard, outdoor BBQ's and Castaway's ocean front bar & grill. Parking is super convenient & free. Free trolly rides to Whalers village and Ka'anapali restaurants, markets and golf courses.

A bright living space features a dining area with a round table and four blue chairs. Natural light floods in from large windows, complementing the neutral walls. A cozy seating area is visible in the background, showcasing a TV and vibrant decor.

4.95 out of 5 average rating, 111 reviews

3-min Walk to Beach, Modern & Fun Condo

- Walk across the street to beautiful, uncrowded Kahana Beach - Beach Bag, Beach Towels, Beach Chairs and Umbrella Included Free - See sea turtles and monk seals swimming in the ocean - 8 minute drive to Ka'anapali and Kapalua golf courses - Arcade machine with classic 80's games - Drop down bar on the lanai - A/C in the bedroom and living room - King size bed and queen sleeper sofa - Cable TV and smart TV, WiFi stereo - Walk to nearby groceries, restaurants, and bars - Fast WiFi

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.

4.86 out of 5 average rating, 294 reviews

Kaanapali Shores Double Oceanview Resort Living

Your perfect Maui vacation! The west side of Maui is where it’s at and it gets no better than Kaanapali Beach, recognized worldwide as one of the top beaches anywhere. Add our gorgeous yet sensibly priced condominium and you have it all. Oceanfront views from both the very private, quiet, cool lanai (balcony) and master bedroom including the beautiful Molokai island, and views of the West Maui mountains are just the beginning of the many great reasons to stay in our condominium.

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, 170 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.

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.

4.98 out of 5 average rating, 192 reviews

Sunsets and Turtles and Whales, Oh My!

Spectacular ocean views Whales and turtles galore(whale season Nov-March) Great snorkeling Gorgeous landscaping Pool, grills, shuffleboard, laundry, and huge sundeck Pristine beaches, grocery stores and world class shopping nearby Sleek and modern Maui hale Chef's kitchen Stainless steel appliances Tv & wifi Cali King bed with luxury linens Beach toys Cooling trade winds Boutique building Elevator and luggage carts Free parking

4.96 out of 5 average rating, 447 reviews

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, 150 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, 193 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.

4.99 out of 5 average rating, 110 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

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.

4.93 out of 5 average rating, 193 reviews

Maui Eldorado Resort Ka’anapali & Whalers Village

The living area showcases a spacious seating arrangement facing an unobstructed ocean view through large windows. A dining table is visible nearby, accompanied by a ceiling fan and modern decor. Natural light enhances the airy feel, while the tranquil ocean can be seen in the distance.

4.89 out of 5 average rating, 146 reviews

Absolutely Oceanfront - Corner Unit- Amazing Views

4.96 out of 5 average rating, 136 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!

5 out of 5 average rating, 17 reviews

A resort landscape is depicted, featuring a lagoon-style pool surrounded by palm trees and lounge areas. Ocean waves gently lap at the shore in the background, with a clear blue sky above. The building architecture showcases multiple levels, blending naturally with the tropical environment.

Villa in Lahaina

Westin Nanea Kaanapali Ocean Villa 2BR Sleeps 6

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, 56 reviews

Westin Kaanapali Resort North Studio Villa

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.

4.87 out of 5 average rating, 123 reviews

Condo in Lahaina, New Remodel, Amazingly Peaceful

4.97 out of 5 average rating, 131 reviews

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

A comfortable living area features a spacious sectional sofa adorned with decorative pillows. A unique coffee table sits at the center, complemented by a woven basket. The kitchen bar, equipped with high stools, reveals stylish tiles, while large windows allow natural light to filter through.

4.97 out of 5 average rating, 29 reviews

Newly Remodeled Ka'anapali Ali'i suite #236

Family- and pet-friendly home rentals

4.78 out of 5 average rating, 293 reviews

A well-appointed bedroom features a spacious bed with decorative pillows and a quilted coverlet. Wall-mounted lighting provides soft illumination. Floor-to-ceiling curtains drape over a window, allowing filtered light to enter. A modern ceiling fan above adds comfort to the room.

Apartment in Kihei

Ocean View-FULL AC-BEACH Kihei Maui

4.98 out of 5 average rating, 119 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

Superhost

A dining table is set on a balcony, featuring two plates and glasses filled with pink drinks. Lush green table mats complement the scene, with a pineapple as a decorative centerpiece. In the background, palm trees sway gently against a bright blue ocean and sky.

4.88 out of 5 average rating, 183 reviews

Beachfront Oceanview Seaside Retreat SoothingWaves

4.99 out of 5 average rating, 355 reviews

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.

Farm stay in Haiku

Maliko Retreat

4.97 out of 5 average rating, 131 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, 517 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

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, 125 reviews

A jewel on Oceanfront & Breath Taking Views.

4.93 out of 5 average rating, 380 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!

Family-friendly home rentals with a pool

5 out of 5 average rating, 51 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!

4.92 out of 5 average rating, 77 reviews

Home in Kaanapali

#1 Kaanapali Beach, Ocean View MER K218

A welcoming outdoor seating area features a small table set with a wine bottle and glasses, accompanied by a bowl of fruit. Lush green grass stretches out to a view of palm trees and the ocean in the background under clear blue skies.

5 out of 5 average rating, 91 reviews

Amazing Oceanview, Kaanapali Beach, Prime Location

4.95 out of 5 average rating, 165 reviews

A covered private lanai features a comfortable seating arrangement with a coffee table, while natural light enhances the space. Sunset views are visible through palm trees, providing a serene backdrop. The entrance to the indoor living area is seen through glass doors.

Flat in Wailea

Ocean Front Vibes Maui

A studio bedroom features a wooden bed frame with a neatly made bed. Two bedside tables with lamps are positioned on either side. A decorative painting hangs above the bed, and a flat-screen TV is mounted on the wall opposite. Natural light fills the space through a nearby window.

5 out of 5 average rating, 40 reviews

Maui El Dorado Kaanapali Beach Studio - G204

A bright living area is featured, showcasing a comfortable seating arrangement with tropical-themed cushions and a glass coffee table. Large windows offer views of lush greenery, while a dining table for four is positioned nearby. A TV is mounted on the wall opposite the seating.

4.92 out of 5 average rating, 91 reviews

Beachfront Resort! Easy Access Ground Floor Condo

A large pool area is surrounded by palm trees and lounge chairs. The clear blue water reflects the sun, while shaded umbrellas offer respite nearby. In the background, resort buildings and lush greenery are visible under a bright sky.

4.91 out of 5 average rating, 11 reviews

Affordable Maui Resort Condo @Kaanapali Beach Club

A sandy beach is bordered by gentle waves lapping at the shore, with lush green trees providing shade. The distant view features a mountain range under a clear blue sky, creating a serene coastal backdrop. The image captures a tranquil outdoor environment ideal for relaxation.