The 9 Best Maui Vacation Rentals of 2019

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The Rundown

Best Overall: Book Kihei Beachside Penthouse at Airbnb "The highlight is the top-floor lanai with its magnificent ocean and mountain views."

Best Budget: Book Ma’alaea Oceanfront Room at Airbnb "Perfect for breakfast overlooking the ocean – and a palm-fringed swimming pool."

Best for Families: Book Kihei Indoor-Outdoor House at Airbnb "This plantation-style house is situated just steps from Charley Young Beach."

Best for Romance: Book Haiku Haleakala Cottage at Airbnb "Set amidst lush tropical gardens on an organic estate in Huelo."

Best Luxury: Book Wailea Luxury Villa at Airbnb "The house wows with chic furnishings and a jaw-dropping rooftop living space."

Best for Large Groups: Book Ocean View Kaanapali Vacation Estate at Airbnb "The master suite is particularly impressive, with its own ocean-view lanai."

Best Inland: Book Keokea Charming Artist’s Studio at Airbnb "The decor is both contemporary and charmingly rustic".

Best Farm Stay: Book Makawao Ocean View Private Cabin at Airbnb "Boasts panoramic ocean, jungle, and mountain views."

Best Camper: Book Paia Suite Vans at Airbnb "Travel all over the island in this 2017 Ram ProMaster."

Our Top Picks

01 of 09

Best Overall: Kihei Beachside Penthouse

Maui Airbnb

Airbnb

Bedrooms (2)

  • 6 guests

  • 1 Queen bed

  • 1 Bunk bed

Amenities

  • Full kitchen

  • Wi-Fi

  • Gym

  • Pool

Located next to beachfront Waipuilani Park in beautiful Kihei, this penthouse apartment is an Airbnb Plus property with excellent guest reviews. With two bedrooms (one with bunk beds and a crib) and two bathrooms, it can accommodate up to six people and is ideal for families. The tastefully decorated, open-plan living space is divided between a full kitchen, dining area, and living room. Amenities range from a dishwasher to a smart TV with Netflix and a game console. For most guests, the highlight is the top-floor lanai with its magnificent ocean and mountain views. You’ll also have access to the apartment's swimming pool, tennis courts, and gym. 

02 of 09

Best Budget: Ma’alaea Oceanfront Room

Ma’alaea Oceanfront Room

Courtesy of Airbnb

Bedrooms (1)

  • 2 guests

  • 1 Queen bed

Amenities

  • Wi-Fi

  • Microwave

  • Coffeemaker

  • Pool

If you're eyeing a more budget option, consider this shared condo in Ma’alaea, a district on the west coast of Maui. The owner lives in the condo full-time, but you will have your own private room with a queen bed, cozy seating area, and basic self-catering items (including a mini-fridge, microwave, and coffeemaker). You’ll have access to a shared bathroom and lanai – perfect for breakfast overlooking the ocean – as well as a palm-fringed swimming pool set amidst the property’s expansive green lawn. Complimentary snorkeling gear, beach chairs, and a cooler come in handy when exploring the surrounding area. Be aware that the owner implements quiet hours from 7 p.m. 

03 of 09

Best for Families: Kihei Indoor-Outdoor House

Maui Airbnb

Airbnb

Bedrooms (3)

  • 6 guests

  • 1 King bed

  • 2 Queen beds

  • 2 Single beds

Amenities

  • Full kitchen

  • Washer/dryer

  • Pool

  • Dishwasher

An Airbnb Plus property in Kihei, this plantation-style house is just steps from Charley Young Beach. It’s ideal for extended families, with three bedrooms capable of accommodating an adult couple each and two single beds for smaller children in the master bedroom. If you’re vacationing with a baby, the Pack n’ Play and high chair make it easy to travel light, while three full bathrooms mean you never have to queue for a shower. The spacious living area includes an open-plan kitchen, dining room, and living room. Outside, there’s a heated saltwater pool and a shaded lanai complete with a barbecue grill – perfect for family fun in the sun. 

04 of 09

Best for Romance: Haiku Haleakala Cottage

Maui Airbnb

Airbnb 

Bedrooms (1)

  • 2 guests

  • 1 California king bed

Amenities

  • Full kitchen

  • Pool

  • Private hot tub

  • Wi-Fi

For a property that offers equal amounts of romance and remoteness, choose this cozy studio cottage. Set amidst lush tropical gardens on an organic estate in Huelo, it’s ideal for exploring Maui’s unspoiled North Shore. In between adventures, sleep in on the California king bed, prepare delicious meals for two in the full kitchen, or spend lazy afternoons soaking in the private, outdoor hot tub. There’s also an outdoor shower, a charcoal barbecue, and a shared swimming pool. Internet and cell reception are spotty – giving you the perfect excuse to unplug and reconnect with each other. In addition, the Superhost owners live on-site and can offer insider info about the island.

Continue to 5 of 9 below.
05 of 09

Best Luxury: Wailea Luxury Villa

Maui Airbnb

Airbnb

Bedrooms (4)

  • 10 guests

  • 4 California king beds

Amenities

  • Rooftop infinity pool

  • Hot tub

  • Full kitchen

  • Washer/dryer

This luxury villa enjoys an enviable address in Wailea, an upscale resort community on Maui’s west coast known for its stunning beaches and championship golf courses. Designed by its architect owner, the house wows with chic furnishings and a jaw-dropping rooftop living space. Spend your days admiring ocean vistas from the infinity pool or hot tub and your evenings watching the sunset while cooking on the grill. Inside, all four bedrooms have California king beds and memory foam mattresses. Both living rooms are equipped with the latest smart TVs and sound systems, while the kitchen boasts a marble-topped dining table and beach-view terrace. 

06 of 09

Best for Large Groups: Ocean View Kaanapali Vacation Estate

Maui Airbnb

Airbnb

Bedrooms (6)

  • 16+ guests

  • 3 King beds

  • 4 Queen beds

  • 2 Double beds

Amenities

  • Pool

  • Full kitchen

  • Barbecue grill

  • Indoor & outdoor dining

This Superhost-owned house presides over a private cul-de-sac on the Kaanapali Royal Golf Course, within walking distance of the beach. With six bedrooms, seven bathrooms, and space for 16 or more guests, it’s the perfect choice for family reunions and celebrations. The master suite is particularly impressive, with its own ocean-view lanai, king-size bed, and jetted spa tub. Spend quality time playing in the infinity-edge pool or relaxing in the hot tub. The pool deck also overlooks the sea and comes with plenty of comfortable rattan furniture and a built-in barbecue for big al fresco meals. Inside, there’s a full kitchen, an enormous dining table, and a basement TV and game room. 

07 of 09

Best Inland: Keokea Charming Artist’s Studio

Maui Airbnb

 Airbnb

Bedrooms (1)

  • 2 guests

  • 1 Queen bed

Amenities

  • Smart TV

  • Kitchen

  • Garden

  • Outdoor shower

If a beachfront location isn’t essential, consider immersing yourself in authentic island life at this beautifully decorated, Airbnb Plus studio instead. It's set on a five-acre mountainside property near Keokea and belongs to renowned Maui artist Curtis Wilson Cost. The decor is both contemporary and charmingly rustic (imagine crisp white linens and plenty of exposed wood). The open-plan space includes a comfortable queen bed, a small kitchen and dining area, and a full bathroom. Head outside onto the patio to shower beneath the stars, or explore a sculpted garden path that leads you to a secret gazebo — perfect for al fresco meals overlooking the distant sea.

08 of 09

Best Farm Stay: Makawao Ocean View Private Cabin

Maui Airbnb

Airbnb 

Bedrooms (2)

  • 4 guests

  • 1 King bed

  • 1 Sofa bed

Amenities

  • Full kitchen

  • Smart TV

  • Washer/dryer

  • Luggage drop-off

You can experience Maui’s artisan farming culture firsthand at this beautiful cabin, situated on a 20-acre coffee plantation near Makawao. It boasts panoramic ocean, jungle, and mountain views, as well as two bedrooms, one bathroom, and a full gourmet kitchen. You’ll even be able to brew your own coffee using the farm’s award-winning beans. The cabin has Wi-Fi, Netflix, and cable TV, although you’re likely to spend most of your time outside – either barbecuing on the lanai or exploring the farm’s private hiking trails and natural swimming pools. You can pick your own flowers, fruit, and herbs, while a complimentary farm tour includes a hike to some ancient Hawaiian pictographs. 

Continue to 9 of 9 below.
09 of 09

Best Camper: Paia Suite Vans

Maui Airbnb

Airbnb

Bedrooms (1)

  • 2 guests

  • 1 Queen bed

Amenities

  • Solar power

  • Wi-Fi

  • Kitchen

  • Air conditioning

Can’t decide where you want to stay in Maui? Travel all over the island in this 2017 Ram ProMaster, which has been lovingly converted into an off-the-grid camper van that blends the freedom of camping with home luxuries. It’s completely solar-powered and includes air-conditioning, electricity, and Wi-Fi. The queen bed has proper sheets and pillows and overlooks a large window so you can wake up to views of the beach or mountains. There’s space to stand up and walk around without having to rearrange the furniture, while a compact kitchen allows for self-catering with all cookware, coffee, and spices included. There's even hot water and a toilet.

Need more help planning your trip to the island? Check out our article on the top things to do in Maui.

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