Family-friendly vacation rentals in Kaanapali

4.83 out of 5 average rating, 144 reviews

A spacious living area is furnished with two light-colored sofas adorned with patterned cushions. A glass coffee table sits at the center, complemented by a potted plant in the corner. Natural light enters through large windows with sheer curtains, enhancing the inviting atmosphere.

Condo in Wailea

Beautiful Palms At Wailea #608-2 BR/2 BA

Beautiful Palms At Wailea Condo, located in the heart of Wailea, surrounded by $mil.homes. 5* location. Vinyl wood flooring & Split Air-Cond. system in hallway & in master-B/R. Fans through-out. Immaculately clean & comfortable. Walking distance to shops, hotels, restaurants, beaches.1200 sq. ft., 2BR/2Ba, wide open floor plan ,2nd. fl.unit. Low rise complex. Very private. Large lanai . Barbecue grills located near entryway of complex. Views from the Club House & Pool.The best place to stay!

A person stands in the ocean water, silhouetted against a vibrant sunset with shades of orange and gold. Gentle waves lap at the shore, reflecting the warm colors of the sky, while clouds drift above, adding texture to the scene.

4.89 out of 5 average rating, 128 reviews

Incomparable Maui Sunset condo, includes all taxes

This Renovated, beach themed condo in the Oceanside Maui Sunset is shaded from the afternoon sun on the B side. Our rate includes the 19% state tax! 2 full bathrooms, a new 75" TV, stove, dwasher quartz counters and new thick futon mattresses. The view from the lanai is over the resort's beautiful grounds (with largest private pool in Kihei) to the ocean. Good architecture and concrete construction keep units in this well managed complex private and safe. High speed internet (196Mbps).

An inviting living area features a wooden TV stand with a flat-screen television and decorative accents. A cozy chair is placed beside a round coffee table, which holds a travel book. Light filters through the space, complemented by a potted plant.

4.83 out of 5 average rating, 158 reviews

Awesome Maui home away from home. Covid Cleaned.

A/C throughout. Work desk with dependable wi-fi. 2 Cable TVs . Grass area off lanai. Walk to the beach, stores, restaurants, the park or bus stop. Full kitchen, W/D, 2 queen beds and 1 queen sofabed, 4 beach chairs, 4 beach towels, a beach umbrella and travel cooler, Pak-n-Play, Booster Seat, 2 pking spaces. This condo is comfortable and well-eqipped for a wonderful stay and vacation on Maui. The pool, jacuzzi and BBQ area will be closed for renovation from July8- early October.

4.94 out of 5 average rating, 141 reviews

An outdoor dining area is surrounded by lush tropical greenery. A wooden table is positioned beneath a shaded umbrella, featuring tableware and glasses set for a meal. Textured seating complements the rustic table, creating a serene place for dining al fresco.

Townhouse in Lahaina

Awesome Beach Home - Elegant 3 bed w AC - Families

Spacious, Elegant Villa featuring sparkling white quartz kitchen, central air, luxury bedding, quality teak wood furnishings, theater 80-inch smart TV, two-car garage, beach gear, private lanai, and entertainment area with gas BBQ grill. Our beautiful home is directly across from the famous white sands of Napili Bay, where you can enjoy swimming, snorkeling with turtles, body surfing, stand-up paddle boarding, soaking up the sunshine, building sandcastles, and watching spectacular sunsets.

4.82 out of 5 average rating, 150 reviews

2 Bdrm/2 Bath Condo Steps to Kamaole III Beach

Steps away from parks, beach, restaurants, art and culture. We have a fully stocked kitchen, washer and dryer, entertainment center with Smart TV and lanai with a light/fan and table and chairs. We host couples, solo adventurers, business travelers, and families. Our high ceilings are open air, (shoji (sliding) or wall at primary bedroom do not meet the ceiling). Condo is clean, we have beach towels, beach chairs, & WiFi! The condo has a dedicated parking space for your rental car.

4.92 out of 5 average rating, 218 reviews

Cottage in Maui County

Ualani Retreat. Private Ocean View Cottage.

Private Detached stand alone cottage home on 3 acre retreat. Beautiful ocean and mountain views. Lush Haven surrounded by fruit trees and bamboo groves. Nicely equipped kitchen. Laundry room. Cable TV. Wi-Fi. Delightful Island Home. Very Comfortable. Hot Tub. Close to enjoy some of Maui's best attractions - Haleakala Volcano, Road to Hana, Waterfalls & Baldwin Beach. Locally Owned & Occupied B&B PERMIT : BBPH 2012/0002 SUP2 2012/0001

4.91 out of 5 average rating, 199 reviews

A pathway lined with lush greenery leads toward the ocean, bordered by tropical plants. Barbecue grills are visible to the side, providing outdoor cooking options. The serene water can be seen in the background, complementing the tranquil setting.

Condo in Wailuku

Rare Beachfront Ground floor Oceanview from Lanai!

Enjoy a Romantic yet affordable Direct BeachFront, Ground floor condo with a partial ocean view from the Lanai. NOT ACROSS THE STREET FROM THE OCEAN! Located on gorgeous Sugar Beach, Maalaea- the LONGEST WALKING BEACH on the entire island. Humpback Whales (Nov-April) and turtles are often seen in the waters. On a a quiet, non-through road, this is like your own little neighborhood paradise! GE-210-827-7760-01 TA-210-827-7760-01 General Excise/Transient Tax

A well-appointed bathroom features a circular mirror above a sink with a mosaic-style countertop. The shower is enclosed with glass, displaying tiled walls and a subtle pebble floor. Artwork depicting aquatic scenes adorns the wall, adding a tranquil touch to the space.

4.82 out of 5 average rating, 171 reviews

Spectacular Direct Ocean Front location!

Spectacular oceanfront location only steps away from the beach! This stunning space provides everything a Maui vacation should offer. Positioned right on the water, this quaint condo offers direct ocean views and access along with a dreamy sight of the West Maui mountains. Wake up in paradise to the sound of the ocean waves crashing right outside your door!

A storage area is shown, featuring an assortment of beach gear including cooler, chairs, and bags. Bright blue shelves hold additional items, while a lit corner enhances visibility. The space is organized, providing easy access to essentials for beach outings.

4.94 out of 5 average rating, 112 reviews

Family Friendly Condo! Best Location!

Escape to Maui! Family Friendly Condo with Discounted Rates - Book your Tropical Getaway Now! Due to last minute cancellations, we are offering a HUGE DISCOUNT off our normal rates for our family friendly 2-bedroom, 2-bathroom (2 bathtubs) beach condo. If you are looking for the perfect place for your family to call home in Maui, this is it!

A tranquil shoreline is depicted with gentle waves lapping at the sandy beach. In the background, a mountain range is visible, topped with wind turbines. The scene is bathed in soft, natural light, creating a serene coastal atmosphere.

4.86 out of 5 average rating, 264 reviews

Newly remodeled and close to beaches, shopping!

Newly remodeled condominium with all new furniture and appliances. Our condo is located within walking distance to restaurants and shopping. We are located directly across the street from Charlie Young Beach. Swimming pool and tennis courts, quiet location, nice views and plenty of parking. TA-143-927-7055-01

4.79 out of 5 average rating, 160 reviews

A modern living room features a comfortable gray sofa with decorative pillows, a wooden coffee table, and a large flat-screen TV mounted on the wall. Light streams through expansive glass doors, leading to an outdoor lanai, with a dining area visible in the background.

Apartment in Kihei

Beautiful Remodel Great Value Book Now!

This beautiful remodeled Two-bedroom/One bath condo is only 126 steps from the beach!! Enjoy beautiful sunsets and long walks on miles of beautiful beach! Watch the whales in the bay and enjoy snorkeling, swimming and boarding. This spot is a well kept secret - close to shopping and dining spots!

Vibrant bougainvillea flowers in shades of pink are seen in the foreground, framing a tennis court in the background. The court features a green surface, with a net visible and surrounding palm trees, suggesting a tropical setting.