Guesthouse vacation rentals in Maui County

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Top-rated guesthouses in Maui County

Guests agree: these guesthouses are highly rated for location, cleanliness, and more.

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Guest favourite

Guesthouse in Kula

4.98 out of 5 average rating, 168 reviews

Upcountry Alpaca, Llama, and Rabbit working farm

Experience Maui's first working fiber farm, home to Alpacas, Llamas, and Angora rabbits. Sitting at 3300 ft above sea level, Cottontail Farm enjoys perfect weather days and crisp, cool nights. The cooler temperatures are perfect for our wool producing animals that graze just outside your cottage in the back yard. Our alpacas and llamas are quiet observers but also provide plenty of entertainment of their own. Our group of Angora rabbits can be seen out the window hopping around their enclosures.

Jan. 14 – 21

$443 CAD per night

Guest favourite

Guesthouse in Paia

4.9 out of 5 average rating, 40 reviews

Bright, spacious, private plantation style studio.

BBWK 2014/0002. TA146617958401, We are located in a residential neighborhood on the north shore of Maui in an area of Pa’ia known locally as Spreckelsville or Sprecks. It is conveniently located just off the Hana Highway halfway between the town center of Pa’ia, which is Baldwin Avenue, and the Kahului Airport (where kite beach is located) so you will hear the airplanes taking off in the distance. 7/14 day minimum. No pets. You can drive to Kite Beach or Baldwin Avenue in around 10-15 minutes.

Apr. 3 – 10

$372 CAD per night

Guest favourite

Guesthouse in Hana

4.85 out of 5 average rating, 89 reviews

Ohana Cottage, Hana, Maui, HI

Located 10 minutes from Hana town. Step out your door to a lovely walk along the ocean cliffs. The elevated cottage captures tropical breezes passing through aromatic trees; air flows through screen doors on all sides of the cottage. A screened breakfast nook connected to the kitchen. Ceiling fans add additional air flow to comfort on the warmest days and nights. Kitchen amenities include countertop appliances, electric range stove, full size refrigerator & an electric grill. Smart TV / Wifi.

Oct. 18 – 25

$610 CAD per night

Guest favourite

Guesthouse in Kihei

4.99 out of 5 average rating, 67 reviews

Stunning remodeled treehouse cottage with views

Our cozy cottage is close to the beach, family-friendly activities, nightlife, public transport, tennis court, gym, shopping, bike rentals, and much much more right in central Kihei. Hosts live on property and are extremely accommodating and helpful. Enjoy the partial view of the ocean and spectacular morning views of Haleakala. The private outdoor patio/lanai is ideal for private sunset views, and meals. Licensed with the County of Maui B&B License BBKM20090013 TMK (2) 3-9-033:019

Nov. 18 – 25

$324 CAD per night

Guest favourite

Guesthouse in Haiku-Pauwela

4.97 out of 5 average rating, 374 reviews

Quaint Cottage Near Coffee, Road to Hana/Haleakala

Located on the quiet north shore, 1 hour from the fire area- on the opposite side of the island. Ideal for returning visitors that like to explore during the day and relax quietly at night or exploring the road to Hana / Haleakala. Wander to the coffee shop for breakfast. Adventure the road to Hana, Haleakala or a nearby beach. Refresh in the warm outdoor shower. Admire the unique, colorful homemade decor. Imagine yourself living here forever. Repeat! (Daily guest cottage life!)

Dec. 6 – 13

$489 CAD per night

Superhost

Guesthouse in Wailuku

4.87 out of 5 average rating, 218 reviews

2B/2Bcottage/central/private/ historic town/wi-fi

2B/2B cottage , attached to a plantation home, in the heart of Maui, in historic Wailuku town...home of the famous Iao theater and minutes from Iao valley & the famed "Needle mountain ". Private, fully furnished, and equipped with all amenities needed for a comfortable short-term stay. Well located to connect you to all parts of the island within a 10-30 minute drive. It's great for business travelers doing business in Wailuku , hikers ,bikers, and true hawaiiana seeking tourists .

Nov. 17 – 24

$425 CAD per night

Superhost

Guesthouse in Wailuku

4.89 out of 5 average rating, 171 reviews

Cozy 1BR near Iao Valley w Outdoor Living Space!

The Blue Door on Church Street is the perfect home for your Maui adventures. Get out of the hectic hotel zones and experience Hawaii in relaxed, luxurious accommodations. We are nestled below beautiful I'ao Valley in historic Wailuku Town. Walk to shops, restaurants, coffee, yoga, theatre, food trucks, and more. A short drive from I'ao Valley, Whole Foods, beaches, the MACC, and 15 min from the airport. Sleep deeply on a King size Nectar mattress. @bluedoormaui

Jun. 15 – 22

$392 CAD per night

Guest favourite

Guesthouse in Haiku-Pauwela

4.93 out of 5 average rating, 135 reviews

Maile Bungalow- County Licensed

Maui County License: BBPH2009/0012 (taxes included in rate) Lovely cottage with ocean and country views, surrounded by tropical flowers and fruit trees located in a small quiet and peaceful neighborhood in Ha'iku. The cottage is off the road and the neighborhood has no through traffic. Walking distance (15min) to Ha'iku's Market Place and bus stop. The cottage is well equipped with all amenities you need to feel home.

Nov. 15 – 22

$593 CAD per night

Guest favourite

Guesthouse in Maui

4.93 out of 5 average rating, 158 reviews

South Maui Oceanview Solo Cottage

Formosa Makamae Villa is a solo, quiet 700 sqft studio and 250 sqft deck property. An open deck facing the seaside boasts a 360 degree panoramic view from the foot of Haleakala to Molokai island. Beach access is just 3 min by car to Keawakapu beach, 7 mins to Wailea beach. We have a kitchen, refrigerator, washer and dryer etc. whole cottage are available for 4 persons families. Our current rate is $288 per night.

Aug. 21 – 28

$463 CAD per night

Superhost

Guesthouse in Kihei

4.84 out of 5 average rating, 131 reviews

Kihei Cottage by the Beach

Aloha! Welcome to one of the best locations on the island! We are a legal and licensed vacation rental with the County of Maui. Located just under half a mile (or 5 minute walk) from the beach, surfing, park, restaurants, shops and stores. Our private 1 bedroom 1 bathroom cottage offers complete relaxation for the perfect Maui vacation. There is air condition in both the bedroom and living space of the cottage.

Nov. 7 – 14

$408 CAD per night

Guest favourite

Guesthouse in Lanai City

4.89 out of 5 average rating, 340 reviews

de Brums Lanai/BBLA 2021/0001

Our one bedroom cottage rests on the hill above Lānaʻi. It offers a complete kitchen and a lovely view from the covered lanai. Shady and cool, we are a 12 minute walk into town. There is no need for either AC or heat. While we do have ceiling fans in every room, you will find Lānaʻi to have a lovely climate with tropical breezes during the day and cool, upcountry temperatures for great sleep in the evenings.

Dec. 9 – 16

$342 CAD per night

Guest favourite

Guesthouse in Paia

4.97 out of 5 average rating, 64 reviews

Maui by the Sea ocean view cottage

Welcome to Maui by the Sea on the North Shore of Maui, Hawaii! Maui by the Sea is a beautiful permitted vacation rental - an ideal ocean-view cottage located ocean front between Paia and Ho’okipa, on Maui's scenic and exciting North Shore With 23 years of experience, Maui By The Sea has always operated under a legal County of Maui permit and our current permit is valid through 2031.

Aug. 12 – 19

$602 CAD per night