Holiday houses in Maui County

The Blue Door on Church Street | Spacious Two Bedr

Enjoy Haleakalā views from this spacious two-bedroom upstairs retreat at The Blue Door on Church Street, a restored 1930s plantation home in historic Wailuku. Features include a king Helix bed, queen Helix bed, full-size memory foam sleeper sofa, full kitchen, rainfall shower, AC, fast WiFi, Smart TV, parking for two vehicles, and a large private deck with outdoor dining and lounge seating. Walk to local cafés and restaurants, or drive minutes to ʻĪao Valley, beaches, hikes, and Maui attractions

Family · Location · Outdoor spaces

Lanai Gem 3-Bdrm Plantation Home Near Town Square

Ideal location. Five-minute walk to Dole Park (Town Square), restaurants, movies, shops, cafe, markets, art gallery. Spacious original plantation home. Full kitchen. Refrigerator/freezer, stove/oven, washer, dryer, kitchen appliances. Free wi-fi. Much lower cost than a small hotel room. Free parking on-property. Nightly rate includes 4.712% GE tax, 10.25% TA tax, 3% MCTA tax. E.g = nightly rate $250.09 + $11.78 GE + $25.63 TA + $7.50 MCTA = $295. Lic: TA-079-863-9616-01. Permit STLA20190001.

Family · Value · Getting around

Oceanview Cottage away from heat! w/ County Permit

Closest Airbnb to Haleakala National Park & Road To Hana. Away from 100 degree heat & traffic & yet still close to food & market! Private Cottage on 2acres of orchard on Haleakala, w/ endless pano Bi-Coastal View (Double Ocean View that no other islands have) & night city view! Stunning sunset & starry nights. Two master suites with ensuite Full Baths. For past guests whom love this home, this AirBnB ends on 12/31/26. Hawaii Supreme Court ruled no more short term rental in agriculture lands.

Value · Location · Hospitality

Oceanside 2-Bedroom 2-Bath Cottage, Stunning Views

Relax & enjoy stunning ocean & sunset views, Kepuhi Beach, and Kaiaka Rock from this private two-bedroom, two-bathroom, two-story oceanfront cottage with a large covered lanai. This no-smoking cottage is located at the Kepuhi Beach Resort, close to pristine beaches, trails, and an oceanfront pool. The cottage is a peaceful place to work online, explore, or unplug & relax. You will enjoy blue ocean & beach views, colorful sunsets, breezes, tropical birds, waves, and whales in the winter.

Location · Family · Wi-Fi

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.

Value · Family · Condition

Maliko Retreat

NOTE: This farm stay is not being phased out by County regulations. Many oceanfront condominiums are currently under threat of a phase-out. Farm stays are a "Permissible Use" on agricultural bona fide farms by State of Hawai'i law. Be assured your reservation here will be safe from government interference. This eclectic antique Hawaiian cottage is perched atop a scenic jungle gorge with breathtaking views in every direction. Open and breezy; attention to detail shines from every facet.

Family · Value · Sleep quality

Hana Maui Luxury Elua Cottage

OCEANFRONT SPLENDOUR IN PERFECT HARMONY WITH NATURE This beautiful cottage is set directly on the bluffs of Hana Bay surrounded by beaches and black-lava landscapes. Hana Maui Luxe Elua Cottage is perfectly situated for all kinds of island adventures on the Eastern tip of Maui. The spirit of Old Hawaii lives on in Hana from its long-held traditions to the inspired natural beauty of this idyllic retreat. This cottage has been extensively renovated with updated finishes and furnishings.

Value · Location · Air conditioning

Hana Ocean Palms Bungalow STHA2009-003

Hawaii Tax of 18.42% is included in the price. Our beautiful Island Style home in Heavenly Hana Hawaii is three hundred yards to a magical ocean pool and a one mile coastal walk to a magnificent beach. The house is open to nature, is fully screened, has hammocks and an ocean view. It sleeps six comfortably, is equipped with a full kitchen, and has an outdoor shower as well as a nice indoor shower and tub. The property is full of tropical fruits, flowers, bamboo, and palms

Family · Location · Checkout

Romantic Hamoa Bay Bungalow

The Hamoa Bay Bungalow is Hana Maui's most elegant vacation hide-away. Balinese inspired, private, with ocean views, secluded and romantic. Just beyond sleepy Hana Town... this property is tucked in amongst lush ferns, banana trees, bamboo, colorful heliconias, fragrant ginger, papaya, century old trees, and manicured gardens. Enjoy sea views from each verandah. Listen to only the sounds of the birds, the geckos chirping, and the stones rolling in the surf at night.

Family · Location · Outdoor spaces

Malie at Haiku Garden Cottages Farm Sanctuary

Welcome to Haiku Garden Cottages, a licensed Farmstay and BnB on Maui’s North Shore (Permit BBPH2017/0002). Mālie is a charming cottage where you can sip coffee on the screened-in lanai, wander tropical gardens, and settle into island rhythms. Enjoy ocean and garden views, a private outdoor shower, and peaceful indoor-outdoor living—just minutes from Haleakalā, the Road to Hāna, nearby beaches, hiking trails, local restaurants, and farmers markets.

Location · Value · Pets

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 · Layout

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.

Value · Family · View