Guesthouse vacation rentals in Maui County

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Top-rated guesthouse rentals in Maui County

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

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Top guest favorite

A group of alpacas, varying in color and patterns, stands along a fence in a lush green pasture. Their calm expressions reflect the peaceful environment, with rolling hills and trees visible in the background, creating a serene rural setting.

Guesthouse in Kula

4.98 out of 5 average rating, 257 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.

LocationFamilyTV

The exterior of Villa Paola is showcased in warm sunset lighting, featuring a saline pool surrounded by vibrant greenery. The charming cottage displays a tile roof and is complemented by a hammock nearby, inviting relaxation under the tropical landscape.

Guesthouse in Wailea-Makena

5.0 out of 5 average rating, 4 reviews

Under The Warm Maui Sun

Villa Paola Maui is a 1-bedroom, 1-bath cottage in the Wailea Resort area of Maui, exuding Italian charm. Redesigned with marble, mosaics, and artisanal craftsmanship, it feels like Tuscany. The villa features a well-equipped kitchen, a terrace bar, and a saline pool surrounded by lush foliage. Italian-themed artwork adorns the interior. It's conveniently located near beautiful beaches and world-class resorts. Please note, it's not suitable for weddings, and quiet hours are enforced after 9:00pm

LocationFamilyOutdoor spaces

Top guest favorite

A serene bedroom features large windows allowing natural light to fill the space. A queen bed with a green throw is centered on polished wooden floors. A small table and two chairs provide a cozy seating area, complemented by a vintage dresser and nightstand.

Guesthouse in Makawao

4.95 out of 5 average rating, 121 reviews

Relaxing Upcountry Base for Haleakalā & Beyond

Unlike any other stay! The Romantic Rose Room of our historic Inn is a cozy retreat beneath Maui’s largest Norfolk pine. Guests come here to exhale, reconnect and feel the quiet healing of the land. Enjoy the gardens then head out for adventures to beaches, Haleakala or Hana-creating lasting memories along the way. Beach gear & stadium blankets (for Haleakala) are provided along with"brekky baskets" to start your day. I look forward to sharing this special soulful space with you. BBMPT20200001.

FamilyValueGetting around

Guest favorite

Guesthouse in Wailuku

4.9 out of 5 average rating, 258 reviews

The Blue Door on Church Street | Maui Garden Suite

Stay in the Maui Garden Suite, a cozy private one-bedroom retreat at The Blue Door on Church Street in historic Wailuku. This downstairs space features a king Helix bed, queen sleeper sofa for flexible sleeping, three-room living area, kitchenette, AC, fast WiFi, Smart TV, parking, and a private back patio with outdoor dining, lounge seating, and electric grill. Walk to local cafés, restaurants, shops, and the ʻĪao Theater, or drive minutes to ʻĪao Valley, beaches, hikes, and Maui adventures.

LocationValueNearby

Top guest favorite

A spacious cottage is surrounded by lush greenery and vibrant flowers. The two-story structure features large windows and a welcoming staircase leading to a covered entry. Tall trees provide shade, enhancing the inviting outdoor space.

Guesthouse in Kihei

4.95 out of 5 average rating, 110 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

ValueFamilyAccess

Guest favorite

A cozy sleeping area is shown, featuring a spacious bed with white linens. Two large blue pillows are placed against a natural wood headboard, while a decorative white pillow with blue accents lies in front, adding a touch of color to the overall arrangement.

Guesthouse in Kihei

5.0 out of 5 average rating, 16 reviews

2 min walk to the beach +4 min ->food/drinks/shops

Honu Hale Cottage at Turtle Beach is a spectacular getaway and ideally situated just a few minute walk to a gorgeous expanse of warm sand that extends for miles in each direction and out into the shallow waters of the Pacific ocean where Turtles land to lay their eggs and take a rest. Located in South Maui’s Kihei region, you’ll discover a unique residence that is subdued and far from the congestion of tourist areas, and has the pace of a more authentic Hawaiian way of life. 

ValueLocationBathroom

Top guest favorite

A sprawling tree takes center stage against a backdrop of lush greenery and a blue sky dotted with clouds. Soft sunlight filters through the leaves, creating gentle patterns of light and shadow across the manicured grass of the expansive landscape.

Guesthouse in Haiku-Pauwela

4.88 out of 5 average rating, 146 reviews

Peaceful • Haiku Retreat • Beach 10 & Paia 15 Min

Escape to a spacious studio at Mana Aina, our peaceful 12-acre organic hobby fruit farm in beautiful Haiku, Maui. Enjoy privacy and open space, just 15 minutes from Maui's North Shore beaches. Stroll through tropical gardens, admire the fruit trees, and experience the peaceful charm of Upcountry Maui. Restaurants, beaches, waterfalls, hiking, and the Road to Hana are all nearby, making Mana Aina an ideal base for exploring the island before returning to relax each evening.

LocationFamilyIndoor spaces

Top guest favorite

Guesthouse in Haiku-Pauwela

4.97 out of 5 average rating, 464 reviews

Quaint Cottage Near Coffee, Road to Hana/Haleakala

Located on the quiet north shore, the non-touristy 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!)

LocationFamilyQuiet

Superhost

Guesthouse in Paia

Welcome to Shaka Shack Maui! Ideal location w/ AC

IDEAL LOCATION! This clean, bright, well stocked and fully air-conditioned 2bed 1bath Ohana (cottage) is attached to main house but totally private entry, parking, yard etc.. Shaka Shack offers the best of Maui’s North Shore lifestyle; stylish comfort and ideally located less than one mile from Paia Town, Baldwin Beach, Ku‘au Store, Mama’s Fish House, Mama’s Beach. Enjoy the perfect blend of convenience and serenity close to all the North Shore favorites!

CleanlinessHospitality

Guest favorite

A charming cottage is set on a spacious lawn, surrounded by lush greenery. The exterior features a broad lanai with white railings, providing a welcoming entrance. Tropical trees and plants frame the property, contributing to a serene atmosphere.

Guesthouse in Haiku-Pauwela

4.93 out of 5 average rating, 152 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.

LocationFamilyBackyard

Guest favorite

A cozy living area features a light gray sofa adorned with blue patterned cushions. A round coffee table sits in front, accompanied by magazines. A large mirror reflects the space, while a dining area and outdoor patio can be seen through a sliding door.

Guesthouse in Kihei

4.86 out of 5 average rating, 169 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 conditioning in both the bedroom and living space of the cottage.

LocationValueLong stay

Guest favorite

The studio villa is framed by lush greenery and native plants, with a blend of palm trees and vibrant foliage. A panoramic view of the ocean is visible in the background, set against a cloudy sky as the sun begins to set.

Guesthouse in Wailea-Makena

4.93 out of 5 average rating, 179 reviews

South Maui Oceanview Solo Cottage

Formosa Makamae BnB 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 2 persons families. Our current rate is $288 per night.

LocationValueWifi