House vacation rentals in Kaanapali

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)

Value · Family · Biking

Beautifully Remodeled 3 Bedrooms/2Bathrooms

Aloha and Welcome to our Private 3BR/2BA Stand-Alone Cottage – Perfect Maui Getaway. 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.

Value · Family · Outdoor spaces

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.

Family · Location · Hiking

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.

Family · Value · Air conditioning

12 Minute Walk Kamaole Beach II-Quiet Private Easy

1 bedroom/1 bath suite is self contained, attached ohana (ADU) with private entry. Off street parking is 10 seconds from your door. A five minute drive to Kamaole Beach I, II and III. Ideal for longer stays! Convenient Location, Quiet and Private. Not a condo with condo noise. I am a SUPERHOST, see the 4.97 reviews and comments. INSTANT BOOK for a great stay. All fees and taxes are listed & collected when you book. There are no surprise or additional costs. Permit #BBKM 2O19/OOO2

Value · Location · Access

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

Location · Value · Check-in

Quaint 4-bedroom in Ha'iku, Maui

Bring the whole family to the north shore of Maui and stay in our quaint, plantation-era home! At Kihau Gardens (Maui County STRH Permit #2019/0001 and Hawai'i State TAT #T-036-968-8576) we offer a unique home. On each side of a carport, there are two bedrooms, a living area, a small office space, and one and a half baths. Our home in Ha'iku is the perfect stay for two small families who want to explore the north shore, upcountry, Haleakala crater, and the epic drive to Hana.

Location · Family · Air conditioning

The Blue Door on Church Street | Vintage One Bedro

Stay in a restored 1929 plantation-style retreat at The Blue Door on Church Street in historic Wailuku. This private one-bedroom space features a king Helix bed, queen memory foam sleeper sofa, high ceilings, original wood details, kitchenette, rainfall shower, soaking tub, AC, fast WiFi, Smart TV, parking, and access to a shared infrared sauna. Walk to cafés, restaurants, shops, yoga, and the ʻĪao Theater, or drive minutes to ʻĪao Valley, beaches, hikes, and Maui adventures.

Family · Location · View

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

Location · Family · Access

The Art Estate, Haiku Maui Hawaii

Our spacious, open-floor-plan home has a contemporary style. The secluded 17-acre, lush, tropical estate has exotic varieties of Bamboo, Palms, Avocados, and various fruit trees. Located on the grounds is a private, functioning, award-winning art studio creating films, photography, video installations, and sculpture. If you are looking to explore, we are just a quick ten-minute drive to the best beaches on the North Shore!

Family · Location · Cleanliness

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.

Location · Value · TV

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.

Value · Location · Amenities