House holiday rentals in Kaanapali

4.95 out of 5 average rating, 246 reviews

Home in Wailuku

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

LocationValueAccess

4.97 out of 5 average rating, 295 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 guests max (including kids/infants)

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A wide sandy beach extends along the shoreline, meeting clear blue waters. Guests are seen relaxing under umbrellas, while others stroll along the water's edge. Lush palm trees provide shade in the background, contributing to a serene island atmosphere.

4.92 out of 5 average rating, 147 reviews

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.

ValueLocationAccuracy

4.99 out of 5 average rating, 167 reviews

A charming cottage is nestled among lush tropical foliage, illuminated by warm lights from within. The peaked roof and extensive windows create an inviting atmosphere, while a spacious deck offers a glimpse of the surrounding nature, enhancing a serene setting under the dusk sky.

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.

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4.93 out of 5 average rating, 420 reviews

A sunlit swimming pool is framed by lush green grass, leading to a well-designed single-story home with a distinct round roof. The expansive landscape stretches in the background, providing a view of the ocean and distant mountains under a clear blue sky.

Home in Kula

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.

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The kitchen features light-colored cabinetry paired with granite countertops and stainless steel appliances. A large refrigerator and microwave are visible, along with an oven and stove. A central island with a wooden top provides additional workspace. Soft lighting enhances the functional layout.

4.97 out of 5 average rating, 159 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. 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

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The exterior view shows a charming gray house with white trim and multiple windows. Flower boxes are mounted under the windows, and a concrete pathway leads past the property. Lush greenery and tall trees are visible in the background under a clear blue sky.

4.9 out of 5 average rating, 173 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.

LocationFamilyAir conditioning

4.93 out of 5 average rating, 620 reviews

The spacious studio features a comfortable bed and a seating area with colorful cushions. Large glass doors provide access to a private balcony with stunning ocean views. A flat-screen TV and a ceiling fan are visible, alongside a wooden dresser and a coffee table.

Home in Napili-Honokowai

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

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The exterior of a two-story home is displayed amid lush greenery. A spacious deck is highlighted with white railings and a pergola, complementing the tranquil surroundings. The sky is bright with scattered clouds, enhancing the feeling of openness and serenity.

4.92 out of 5 average rating, 103 reviews

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!

LocationFamilyOutdoor spaces

A modern, two-bedroom home is showcased, featuring a covered lanai with a dining area for six. Large windows provide views of the surroundings, while the exterior combines wood and blue siding against a bright sky and greenery.

4.98 out of 5 average rating, 160 reviews

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.

ValueFamilyBathroom

A panoramic view showcases lush green landscape merging into the blue ocean on the horizon. A variety of trees, including a tall conifer, adds to the natural beauty. The sky is bright with scattered clouds, creating a serene atmosphere.

4.99 out of 5 average rating, 210 reviews

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.

LocationValueQuiet

4.97 out of 5 average rating, 148 reviews

A spacious living area features a comfortable sectional sofa facing a large television. Natural light filters through multiple windows, illuminating the space. Bamboo flooring adds warmth, while a subtle green plant enhances the inviting decor. A sliding door leads to an outdoor dining area.

Home in Napili-Honokowai

Private 4bd Home, Walk to Beach

The Kahana Beach House is a spacious and comfortable home located across the street from a secluded beach. Close to some of Maui's best restaurants, golf, and exciting island attractions the beach house serves as a great central hub to explore the island of Maui. The fully equipped kitchen has everything you need and the outside deck is great for lounging in a hammock or grilling on the BBQ.

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Popular amenities for Kaanapali house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 469 reviews

Home in Wailea

Stunning ocean view Villa, Heated pool, Wailea

FamilyValueAir conditioning

The kitchen and dining area feature modern appliances and a large wooden table surrounded by a built-in bench. Natural light enters through the window, illuminating the granite countertops and stylish cabinetry, while a beach-themed artwork complements the tropical surroundings.

4.88 out of 5 average rating, 120 reviews

Chic Villa 2 | Modern Vibes by the Ocean

FamilyValueAmenities

4.88 out of 5 average rating, 119 reviews

A spacious living area features comfortable seating arrangements with a sectional sofa and wicker chairs. A large mirror enhances the sense of openness. Two televisions are positioned on opposite walls, and the tiled floor is complemented by natural lighting from multiple windows.

Home in Wailea

Condo in Kihei 2 BR - 2 bath Condo

ValueLocationCleanliness

A serene sandy beach is shown with gentle waves lapping against the shore. Sunbathers are positioned leisurely on the sand, and a few umbrellas provide shade nearby. Lush palm trees line the back of the beach, creating a tranquil atmosphere under a clear blue sky.

5.0 out of 5 average rating, 73 reviews

Newly Remodeled Cottage

LocationValueBarbecue

4.88 out of 5 average rating, 42 reviews

A tropical outdoor area features lounge chairs beside a heated swimming pool. Palm trees sway in the gentle breeze, with a shaded seating area visible under a pergola. The expansive ocean view is framed by lush landscaping, creating a serene atmosphere for relaxation.

Home in Lahaina

Serene and Peaceful with Heated Pool

ValueFamilyAccuracy

4.93 out of 5 average rating, 29 reviews

Home in Lahaina

Luxe 3BR Pualei Beach House Retreat

FamilyLocationTV

4.71 out of 5 average rating, 31 reviews

Gram’s Maui Golf Cottage

FamilyLocationLong stay

4.59 out of 5 average rating, 29 reviews

Beautiful 2BR 2 BA Cottage near Beach - ICC 13

LocationValueIndoor spaces

Weekly house rentals

4.92 out of 5 average rating, 232 reviews

Paia cottage walk to town and beach

ValueLocationGetting around

An outdoor lanai features a wooden deck with a table and four chairs, surrounded by vibrant tropical plants and blooming bougainvillea. Sunlight filters through the greenery, creating a welcoming space for relaxation or dining outdoors.

4.91 out of 5 average rating, 105 reviews

Kihei Beach House, 1 Block to the Beach

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The covered private lanai is depicted, featuring seating areas with outdoor couches and ceiling fans. A well-maintained lawn leads up to the entrance. Bright blue skies and soft clouds frame the space, creating a serene outdoor environment for relaxation.

4.84 out of 5 average rating, 114 reviews

Modern Family Kihei Home by the Beach

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A charming cottage is framed by palm trees and lush greenery. The front porch features wide steps leading to a welcoming entrance, with outdoor seating partially visible. The peaked roof adds character, while the clear sky enhances the peaceful tropical setting.

4.97 out of 5 average rating, 133 reviews

Hunter Hales Hoku cottage Haiku Maui

LocationValueTV

A spacious single-story home is surrounded by lush palm trees and vibrant tropical plants. The well-maintained lawn features a mix of greenery, with the house's exterior displaying a neutral tone under a bright blue sky.

4.86 out of 5 average rating, 172 reviews

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

LocationValueAir conditioning

A spacious living area showcases natural wooden elements, with a light-colored bamboo sofa and matching chairs. Large glass doors frame a stunning seaside view, allowing soft light to illuminate the room. A ceiling fan provides ventilation, complementing the relaxed ambiance of the space.

5.0 out of 5 average rating, 25 reviews

Beautiful Beachfront Townhouse !

ValueLocationComfort

4.94 out of 5 average rating, 72 reviews

Milo Surf Cottage

FamilyLocationGetting around

5.0 out of 5 average rating, 22 reviews

A spacious living area is presented with a light-colored sectional sofa and a wooden coffee table. A wall-mounted television is visible, alongside a patterned armchair. Large glass doors open to the lanai, allowing natural light and views of the surrounding landscape.

Home in Kapalua

Relaxation in Kapalua-Specials!

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Private house rentals

An outdoor deck area features a spacious seating arrangement, including a large dining table and comfortable lounge chairs. The surrounding landscape is dominated by green cane fields under a bright blue sky, creating an open and airy atmosphere.

4.92 out of 5 average rating, 59 reviews

Paia Family House

LocationFamilyOutdoor spaces

Two red chairs are positioned on a grassy area overlooking the ocean. Palm trees frame the scene, while gentle waves and a cloudy blue sky are visible in the background, creating a serene coastal setting.

4.96 out of 5 average rating, 82 reviews

Hale Ho'okipa Kai Cottage, County Licensed

ValueLocationKitchen

A bright living area is presented with large glass doors offering views of the ocean. A dining table made of wood is accompanied by light-colored chairs. A potted plant and a unique wood side table add natural elements, while pendant lights provide soft illumination.

4.75 out of 5 average rating, 55 reviews

Kihei 533- OceanView, 5 min drive to stores/food

FamilyLocationWi-Fi

4.9 out of 5 average rating, 10 reviews

Home in Kapalua

Ridge 2621- Luxury Villa w/180 Degree Sunset Views

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A balcony table is adorned with a glass vase filled with colorful flowers, offering a vibrant contrast to the wooden surface. In the background, sweeping views of the ocean and lush palm trees are visible against a backdrop of distant mountains.

4.88 out of 5 average rating, 24 reviews

Stunning Ocean Two Bd Corner Condo,AC,Pool D301

LocationFamilyHospitality

The bright bedroom features a spacious bed with light bedding and a decorative accent blanket. A large window allows natural light to fill the room, complemented by sheer white curtains. A wooden nightstand with a bedside lamp and woven pendant light add warm details.

5.0 out of 5 average rating, 82 reviews

Hookipa Farm: County Legal 3 Bedroom Home in Haiku

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A living area is featured with a cozy sectional sofa adorned with various textured cushions. A natural wood coffee table sits at the center, surrounded by a woven rug. There is a flat-screen television positioned on a wooden console near a large window with greenery outside.

4.97 out of 5 average rating, 31 reviews

Hale Nanea

FamilyLocationLaundry

A serene outdoor area includes smooth stone dipping pools and a Jacuzzi with sunset views. Tropical plants are situated in decorative pots, complementing the landscape. The setting is enhanced by tiki torches, and a lush lawn extends towards the horizon under a soft evening sky.