Family-friendly holiday rentals in Kaanapali

4.98 out of 5 average rating, 135 reviews

Best Location in Kapalua, walk to beach, spacious

Best location spacious 1-bedroom 1-bath Kapalua Bay Villa, walk to Kapalua Bay Beach and Napili Bay -best for swimming and snorkeling. Ideal for families and couples. Modern interior with lots of natural light. Enjoy views and fresh island air from this ground-level unit with large bay windows and a walk-out patio. Walk to Montage, Ritz Carlton, Honolua Store, restaurants (Cane & Canoe, Merriman's, Taverna, Sansei, Seahouse), golf, and tennis. Free parking/wifi. Up to 4 people (including infants

4.94 out of 5 average rating, 130 reviews

Oceanfront Two Bedroom at Kaanapali Shores #504

Enjoy oceanfront views from this 5th floor 2-bedroom / 2-bath condo at the popular Kaanapali Shores Resort. Central A/C, spacious living room, washer/dryer, full kitchen, wifi, cable tv & SNES classic Just steps away from the ocean Watch beautiful sunsets from the resort The resort has pools, hot tubs, restaurant and bar, and more Supermarket across the street *Wildfire Update* This condo is located in North Kaanapali outside the Lahaina wildfire burn zone. West Maui is now open to visitors

4.99 out of 5 average rating, 138 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.

4.99 out of 5 average rating, 134 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, 202 reviews

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

4.94 out of 5 average rating, 138 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.

4.95 out of 5 average rating, 104 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

4.86 out of 5 average rating, 286 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.

4.99 out of 5 average rating, 159 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.

4.96 out of 5 average rating, 144 reviews

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.

4.98 out of 5 average rating, 191 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.