House vacation rentals in Kaanapali

4.98 out of 5 average rating, 115 reviews

Mana Hale Vacation Rental

This private home is nestled in a beautiful garden just 1 mile from the ocean. The house is spacious with 2 bedrooms & 2 full bathrooms. Front and back decks offer ample opportunity for lounging with a good book, grilling, visiting with friends and family or even just a romantic getaway. The house is close to cafe's, shopping, restaurants and many of the idyllic maui beaches. Perfect for retreat, fun and healing in paradise. STKM 2018/0002 HITax # GE-087-066-3168-01 HI TAT # TA-087-066-3168-01

4.97 out of 5 average rating, 269 reviews

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 Adults max plus 1 child under 12 yrs

4.99 out of 5 average rating, 138 reviews

Home in Makawao

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.

4.93 out of 5 average rating, 361 reviews

Home in Kula

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!"

4.87 out of 5 average rating, 157 reviews

Cajudoy's Hale - STKM 2O13-OO18/TA-081-709-8752-01

WONDERFUL! Three bedroom hale (home) in the Central Kihei area of Maui. Wood floors, lots of space, kitchen fully stocked, BBQ and so much more. Great for kids, elderly, and young at heart. This house is your home away from home. We have all of the necessary items for a home. If we do not have something please let us know and we will try our best to accommodated. Walking distance to the beach, shopping, park, public transportation, etc... You will not find a better place in Kihei.

4.96 out of 5 average rating, 249 reviews

Hale Leialoha (BBPH 20 17/00 04,SUP 20 17/00 10)

Hale Leialoha (GE-046-437-3760-01, TA-046-437-3760-01) is a beautiful Hawaiian style cottage located in "upcountry" Maui. Our Cottage is permitted for a total of 4 adults and up to 6 people. The cottage easily fits a family of 6 (4 adults & 2 children or 2 adults & 4 children or 3 adults & 3 children) (License # BBPH 2017/0004, SUP 2017/0010) As our guest, you will enjoy the modern finish and conveniences as well as a large roomy covered deck amidst the casual feel of old Hawaiiana.

Superhost

Home in Lahaina

4.92 out of 5 average rating, 121 reviews

Beautifully Remodeled 3 Bedrooms/2Bathrooms

Aloha and Welcome to our newly remodeled Plantation stand-alone Cottage! This home is just a short 5 minute walk to the best beaches and parks on Maui. 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 air conditioner.

4.92 out of 5 average rating, 133 reviews

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.

4.97 out of 5 average rating, 151 reviews

12 Minute Walk Kamaole Beach II-Quiet Private Easy

This 1 bedroom/1 bath suite is a self contained, attached ohana (ADU) with private entry. Off street parking is 10 seconds from your door. Located a 12 minute walk straight down to Kamaole Beach II. Convenient Location, Quiet and Private. 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

4.96 out of 5 average rating, 440 reviews

Stunning ocean view, heated pool at home by Wailea

Ocean, sunset views, unique home reminiscent of a Victorian villa with heated private pool for guests in the villa, tropical gardens. Home renovated and maintained by designer. Cal King in main, second has twin beds. Pac n play and high chair are available. Open plan living with dining and relaxing on the lanai. Keawakapu beach, Wailea shops and restaurants 5 minutes drive. Your private view retreat. #BBMK 2016/0003

4.9 out of 5 average rating, 188 reviews

GREAT Location HAIKU 3 Bedroom Cottage

COUNTY PERMITTED - This home holds a Legal Maui Permit STPH2015/0006. Amazing Location, Cute Beach-style, 3 BEDROOM +1 BATH home. 2 Queen bedrooms & another bedroom/office with desk + twin bed, walk to Haiku Grocery, Haiku Cannery, Nuka Japanese & Sushi, Yoga, Colleens, 4 miles to Ho'okipa, (sleeps 1-4) fully equipped kitchen, HIGH SPEED WIFI. Washer/Dryer not shared. Please note we host children 6 years & over.