
Family-friendly vacation rentals in Kaanapali
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Kaanapali

Total vacation rentals
Explore 2,800 vacation rentals in Kaanapali

Nightly prices starting at
Kaanapali vacation rentals start at G$2,093 GYD per night before taxes and fees

Verified guest reviews
Over 17,200 verified reviews to help you choose

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Vacation rentals with a pool
2,460 properties feature pools

Rentals with dedicated workspaces
2,070 properties have a dedicated workspace

Wi-Fi availability
2,800 of Kaanapali vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Kaanapali rentals

4.8 Average rating
Kaanapali stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated family-friendly rentals in Kaanapali
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Peaceful Maui Bungalow | Ka Hale Aloha-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!! 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, steps to the ocean & walking distance to 2 beaches. Ka Hale Aloha will make you feel like you’re truly living the island life. * Check us out on IG at @thoughtfulstays

Kula Jewel - Pool, Hot Tub & Awesome Views!
Pamela has been hosting two fully permitted listings for the last 12 years with over 1,500 five star reviews. BUT Kula Jewel, burned to the ground in the Maui wildfires in 2023. We have recently completed building the NEW Jewel, and it is GORGEOUS! We just had our first guests stay, and this was their review: "The Jewel is extraordinary! The views are stunning! I’ve stayed in many Air B&Bs. I give her place my highest rating!" Btw, we have not raised our prices. The service fee now shows.

Sweeping Panoramic Ocean Views - Private Ohana
Live like a local at the Ocean Blue Ohana - the private first floor of this amazing Hawaiian pole home on a half acre property in South Maui. As you enter the space, you will be drawn to the sweeping panoramic ocean views. You are sky-high, perched 500 feet above sea level, looking at the most glorious views of the neighboring islands, mountains, coastline, and Maui's amazing skyline. To top it off, you are 5 minutes from the Wailea Resorts and beautiful golden sand, crystal clear beaches.

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.

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.

Adorable Gingerbread House Farm Stay, Makawao
This LEGALLY PERMITTED Farm Stay has the lush beauty and privacy,, without the drive to Hana! Only 15-20 minutes to the airport, 10 minutes to beaches, 2 minutes to restaurants and shops...on a private gated property with organic nursery. Seasonal stream in the back yard. Simply BEAUTIFUL! We gave 8.5 acres of diversified farm-fruit, water lilies, 10,000 sq ft greenhouse) Comes with a FREE FARM TOUR and/or LABYRINTH WALK with every booking! Permit Number STMP 2015 / 0001 SUP2 2013 / 0013

Maliko Retreat
NOTE: This farm stay is not being phased out by County regulations. Many oceanfront condominiums are currently under threat of a phase-out. Farm stays are a "Permissible Use" on agricultural bona fide farms by State of Hawai'i law. Be assured your reservation here will be safe from government interference. This eclectic antique Hawaiian cottage is perched atop a scenic jungle gorge with breathtaking views in every direction. Open and breezy; attention to detail shines from every facet.

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.

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.

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.

Kalani at Haiku Garden Cottages Farm Sanctuary
Welcome to Haiku Garden Cottages, a licensed Farmstay and B&B on Maui’s North Shore (Permit #BBPH2017/0002). Kalani is a charming cottage where you can sip coffee on the lanai, wander garden paths, harvest seasonal fruit, and settle into island rhythms. Enjoy ocean and garden views, a private outdoor shower, and relaxed indoor-outdoor living—just minutes from Haleakalā, the Road to Hāna, beaches, hiking trails, restaurants, and farmers markets.

#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.
Popular amenities for Kaanapali family-friendly rentals
Family-friendly home rentals with air conditioning

NEWLY REMODELED OCEAN VIEW CONDO, STEPS FROM BEACH

Beautiful Papakea 1 Bedroom with A/C

Stylish Love Hideaway, Maui Kaanapali Oceanfront

Kaanapali Shores Double Oceanview Resort Living

Oceanfront resort, Updated condo, Air Conditioned

MAHANA 505 OCEAN FRONT W/ SPECTACULAR VIEWS

Beautifully Remodeled 3 Bedrooms/2Bathrooms

Best Papakea Oceanfront *No resort fees* Unit A106
Family-friendly home rentals with a pool

Charming Kaanapali cottage with ocean view

Amazing Kapalua ,Stay 7 nights, only pay for 6 !

Stunning Sunset from A103's direct ocean view!

Kapalua, luxe, ocean view, beach, spa, golf/tennis

Eldorado Beach Resort Ka’anapali - Whalers Village

Mahana at Kaanapali- Beachfront Walkout Jewel

Oceanview Kaanapali Shores- Beachfront resort w/AC

Ocean View steps from beach, dining, shopping 723
Family-friendly home rentals with a kitchen

Serene and Peaceful with Heated Pool

Kahana West Maui Beach Condo | Ocean Views & Pool

Oceanfront Mahana Panoramic Pacific Views

Newly Remodeled Cottage

Kaanapali Condo , new pricing discounts

Maui Eldorado J102 - Black Rock and Ocean Views

Your Family's Perfect Island Retreat w/ Full AC

Oceanfront with Panoramic Views I Maalaea Kai 416
When is the best time to visit Kaanapali?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$175,999 GYD | G$167,419 GYD | G$175,790 GYD | G$167,210 GYD | G$148,584 GYD | G$170,767 GYD | G$183,742 GYD | G$179,138 GYD | G$122,634 GYD | G$129,331 GYD | G$133,517 GYD | G$162,187 GYD |
| Avg. temp | 23°C | 23°C | 23°C | 24°C | 25°C | 26°C | 27°C | 27°C | 27°C | 26°C | 25°C | 24°C |
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- Maui
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