Family-friendly holiday rentals in Nāpili Bay

4.98 out of 5 average rating, 246 reviews

A group of alpacas, varying in color and patterns, stands along a fence in a lush green pasture. Their calm expressions reflect the peaceful environment, with rolling hills and trees visible in the background, creating a serene rural setting.

Guest house in Kula

Upcountry Alpaca, Llama, and Rabbit working farm

Experience Maui's first working fiber farm, home to Alpacas, Llamas, and Angora rabbits. Sitting at 3300 ft above sea level, Cottontail Farm enjoys perfect weather days and crisp, cool nights. The cooler temperatures are perfect for our wool producing animals that graze just outside your cottage in the back yard. Our alpacas and llamas are quiet observers but also provide plenty of entertainment of their own. Our group of Angora rabbits can be seen out the window hopping around their enclosures.

A patio table is set with decorative plates, glasses, and a bottle of wine, accompanied by a vibrant flower. Lush green grass extends in the background, with palm trees and a cloudy sky completing the serene view.

4.97 out of 5 average rating, 148 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

A modern living area is depicted, featuring a gray sectional sofa, a sleek coffee table, and a wall-mounted TV. Large sliding glass doors provide a view of the ocean, while the space is illuminated by natural light, enhancing the open, airy feel.

4.97 out of 5 average rating, 191 reviews

Oceanfront Napili Retreat | 1Br Oasis w/Lanai & AC

Watch sea turtles and sunsets from your private lanai just steps from the ocean. This hotel zoned, oceanfront 1-bedroom condo on stunning Honokeana Bay offers a contemporary space designed to create unforgettable memories. Fully remodeled and air-conditioned, this retreat is surrounded by water and just a short walk to Napili Beach, one of Maui’s finest. With no hidden resort or parking fees., this is perfect for anyone seeking a serene and comfortable base to explore all that Maui has to offer!

A lush green lawn is framed by swaying palm trees, leading toward a vibrant blue ocean. In the background, a thatched-roof structure is visible, alongside tranquil water and distant islands. The bright sky adds to the serene coastal atmosphere.

4.99 out of 5 average rating, 111 reviews

Ocean View Studio steps away from Napili Bay! w/AC

Beautiful ocean view, air-conditioned studio is located at Napili Shores Resort! Napili Shores is a stunning, beautifully maintained, ocean front resort that offers 2 pools, hot tub, an onsite surf and snorkel rental shop, 2 restaurants, and is steps away from both Napili Bay and Kapalua Bay. The unit is located on the 2nd floor with privacy and an ocean view, with a king size bed, 55" TV, and a full size, fully equipped kitchen. The unit also includes Tommy Bahama beach chairs for guests use.

A clear blue sky and palm trees frame a sparkling pool surrounded by lounge chairs. A thatched-roof pavilion stands nearby, providing a shaded area with tropical landscaping all around, emphasizing the inviting atmosphere of the resort.

4.88 out of 5 average rating, 144 reviews

Springtime in Napili Shores-Cozy, Oceanside Condo

Napili is the perfect place for your Maui vacation. This beautiful condo’s location is the best mix of resort life and local vibe. Our newly renovated condo is located oceanside and is only a short walk to soft, sandy, quiet beaches. This second floor, corner unit overlooks the beautiful gardens, the tranquil Koi pond and resort swimming pool. The private lanai is the perfect setting to relax and listen to the birds sing, the rustling of the Koi pond and take in the magical Maui ocean breeze.

A spacious studio features a king-size bed with decorative pillows. Light-colored wooden flooring is complemented by a ceiling fan. Large glass doors open to a private balcony with seating for two. A television is positioned across from the bed, enhancing relaxation.

4.93 out of 5 average rating, 103 reviews

Cozy Napili Stay - Beach Access, A/C, fast Wi-Fi

🌴 Our cozy studio at Napili Shores is perfectly located just a 2-minute walk to stunning world-class beaches. Ideal for up to 3 guests, it features a comfy king bed, a sofa bed, and access to two pools, a hot tub, BBQ areas, and onsite restaurants. Spend your days snorkeling, dining, shopping, or golfing—all nearby! 💳 We offer exclusive discounts for DMs! Your peaceful retreat in paradise awaits. Mahalo. 🌺 Still deciding? Add us to your WISHLIST or message me directly if you’re interested

4.97 out of 5 average rating, 243 reviews

A two-story green house is surrounded by lush tropical gardens, showcasing large windows that provide a bright interior. A spacious deck extends from the structure, offering views of the vibrant foliage and the inviting outdoor space.

Cabin in Maui

★Rainbow Lookout - PRIVATE HOT TUB+ACCESS TO POOL

This Stunning North Shore Maui hideaway is surrounded with lush fruit and flower gardens, coconut palms, banana trees, and has easy access to all there is to do on this magnificent island. Stargaze … soak in your own private hot tub with a chilled glass of wine and enjoy a once-in-a-lifetime experience. The 'real' Maui:)! ★Jump Start to The to the Road to Hana! ✔ ★New Cold Central AC ✔ ★Cliff Walk ✔ ★Ocean View✔ ★Private Hot Tub ✔ ★44 ft Swimming Pool ★King Bed ✔ ★Sunrise View✔ ★Star Gazing✔

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, 153 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 & 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.

A dining table is set with plates and utensils, positioned on a lush green lawn. Palm trees surround the area, offering a tropical ambiance with the ocean visible in the background under a partly cloudy sky.

4.91 out of 5 average rating, 148 reviews

OCEAN FRONT Condo at Napili Bay, Near Kapalua!

Thank you for checking out my OCEAN FRONT condo located at the Charming Napili Shores resort. This recently renovated condo is in the high demand I building, which is the closest to the ocean in the complex. Imagine every morning you enjoy the brunch ordered from the famous Gazebo restaurant at your own Lanai right beside the ocean; Soak up the sunshine on the Napili beach steps away from the resort during the day, and come back in the evening to watch the stunning sunset in your room!

4.93 out of 5 average rating, 667 reviews

A charming studio cottage with a distinctive shingle exterior is set among lush greenery. A golden retriever rests on the pathway in front, alongside large trees that provide shade. A vibrant green door invites guests into the cozy interior.

Farm stay in Makawao

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

A view from the lanai features lush green grass and palm trees swaying gently in the breeze. A glimpse of the ocean is visible in the distance, with neighboring buildings set against a clear blue sky.

4.96 out of 5 average rating, 273 reviews

Ocean View Oasis at Napili, West Maui

This air-conditioned studio with beautiful ocean views is located at the oceanfront Napili Shores Resort. The well-maintained resort offers two swimming pools, a hot tub, an on-site surf and snorkel rental shop, and two restaurants, just steps from Napili Bay and Kapalua Bay. The studio is on the second floor for added privacy and ocean views. Inside is a comfortable king-size bed and a fully equipped kitchen. Beach gear and a guitar are provided for easy, relaxed island living.