House vacation rentals in Kaanapali

Priv Hot Tub + Shared Jungle Pool! - Ocean Lookout

Relax and unwind in this stunning private home on Maui's dramatic North Shore, with wraparound lanais, panoramic whitewater ocean, cliff and Haleakala summit views. Star gaze as you 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 AC ✔ ★Private Hot Tub ✔ ★44 ft Swimming Pool ✔ ★Panoramic Ocean Views ✔ ★King Bed ✔ ★Laundry ✔ ★Cliff Walk ✔ ★Star Gazing✔ ★Full Kitchen✔

3B2B w/HotTub FamilyComfort HawaiianaCharm Central

True Hawaiiana charm, comfort, and convenience for your family vacation. Located in the heart of Maui, in historic Wailuku town, with easy access to all parts of the island for all your planned activities. Beaches within 10 minutes drive time in 3 directions and the beautiful West Maui mountains w/ Iao Valley National park behind. After a day of adventure come home to a restful time in the HOT TUB under the bright stars . Walk to boutiquey stores ,Coffee shops, First Friday party w/the locals

Live Like a Local; near Coffee, Road to Hana and Haleakala

Grab a coffee and drive to the beach to catch waves or watch sea turtles nesting in the sand. This peaceful home with a private yard, outdoor shower, and fun surfboard fence is a great base for exploring the Road to Hana or Haleakala. Located on the quiet north shore of maui, 1 hour from popular tourist areas. Ideal for returning maui visitors who want to stay on the north shore or guests splitting their stay between 2 sides of the island of Maui. Sleeps: 4 guests max (including kids/infants)

Private Luxurious Cottage

This marvelous accommodation is for the nature-lover who enjoys luxury. It boasts a lovely deck which looks out onto majestic tall trees and lush green foliage with a romantic soaking tub for two. Centered in the room is a custom-made king-size bed fashioned from cherry wood and adorned with luxurious bedding. There is full kitchen and dining area with views for a tranquil place to share a meal. This is true Hawaiian style where you can enjoy comfortable, elegant and laid-back island living.

Kula Jewel - Pool, Hot Tub & Awesome Views!

Pamela has been hosting two fully permitted listings for the last 11 years with over 1,000 five star reviews. BUT this one, 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: "Pamela’s place is extraordinary! The views are stunning! The design and decor are fabulous in every detail! I’ve stayed in many Air B&Bs; I give her place my highest rating!"

Hunter Hales Hoku cottage, Haiku, Maui

Hunter Hales "HOKU" is one of the two identical 810 sqft cottages on one half acre lot privately located just behind the Haiku Town center. Conveniently located at the start of the Road to Hana. Enjoy the quiet laid back life style of a classic Hawaii country town. You will feel so at home within the detailed cottage, equipped with everything one would possibly need while on vacation. This is local Maui vacationing at its best! TA-192-286-5152-01 STPH 20150004 TMK (2) 2-7-003:135

Beautifully Remodeled 3 Bedrooms/2Bathrooms

Aloha and Welcome to our newly remodeled Plantation stand-alone Cottage! This home is just a short about 5 minute walk (across the street) to the beach and park. Surrounded by lush and tropical landscapes, our 1200 sq ft vacation home (International Colony Club 32) offers 3 bedrooms and 2 bathrooms of comfortable accommodations with 2 King size beds, and 2 Full size beds. The fully equipped kitchen, spacious dining area and living room are open-plan with a comfortable split ACs.

Maui direct ocean front . Super private

Location + Endless Ocean view.This condo is very special! It's Direct Ocean front It really is the best what Maui has to offer. Great for honeymooners, super private. There's not any place closer than the ocean than my condo! You'll feel like as if you were floating above the water when you are in your bed! Please check Wifi user i/d and password once you finished booking. (it's listed). Thanks! Note: this is on the 3rd floor w/o elevators in the building

Modern Family Kihei Home by the Beach

Aloha! Welcome to one of the best located homes on the island! Located just under half a mile (or 5 minute walk) from the beach, surfing, park, restaurants, shops and stores. Our modern property offers complete relaxation for the perfect Maui vacation. Our home offers kid friendly amenities, A/C in ALL ROOMS, an espresso machine and Vitamix. Our calendar is always up to date. Please inquire with any questions, we will respond within 1 hour!

Peaceful and Spacious; North Shore Maui

New, spacious two-bedroom home in Ha'iku, Maui (Permit STPH20200003). With beautiful ocean views and peaceful surroundings, located on the Northshore of Maui, this is the perfect place to stay to explore the Road to Hana, the Northshore, and upcountry Maui. Perfect for two couples or a family, you'll have everything you need to explore the island and a peaceful living area to relax following a day of adventuring.

Charming Hoku Pauwela Breathtaking ocean views!

Located on the north shore of Maui, Hoku Pauwela (Maui County B&B Permit# BBPH 2019/0002 and Hawaii State TAT # TA-036-968-8576-01) is the ideal location from which to experience the north shore, upcountry, Haleakala crater, and the epic drive to Hana. Spacious, quiet, and family-friendly, you'll have all you need to explore Maui and a peaceful living area to relax in after a day of adventuring.

South Maui Guesthouse

This air conditioned very exclusive, private 2-bedroom Guest House is surrounded with lush gardens on a ½ acre property, off the street located in an upscale very private neighborhood (Maui Meadows, above Wailea), yet minutes from the best beaches Maui has to offer. A real Hawaiiian retreat, where you wake up to the sound of birds, not traffic. Permit Number BBKM2018/xxx3 GETxxxxxxxx2801