Cottage holiday rentals in Makena

4.95 out of 5 average rating, 37 reviews

A charming Hawaiiana home is surrounded by lush greenery and vibrant plants. A wooden staircase leads to the entrance, while a gazebo with seating provides a shaded area for relaxation. Bright sky and palm trees frame the inviting outdoor space.

Cottage in Wailuku

3B/2B FamilyVacationComfort HawaiianaCharm Central

Create precious family memories of a tropical vacation in this spacious, Hawaiiana home. It provides a peaceful place to rest after a day of adventure. National treasures like Iao Valley National Park /Needle Mountain and Iao theatre are 5 minutes away. Walk to Boutiquey stores /Wailuku First Friday/ local offerings. Central location with easy access to all parts of the island/Beaches/Amenities/Airport. Be there instead of spending time getting there. Hawaiiana charm, warmth and comfort.

4.95 out of 5 average rating, 399 reviews

A vibrant sunset casts colorful hues across the sky, with layers of pink, orange, and blue blending seamlessly. The foreground features green land and trees. In the background, a cottage rests against the horizon, overlooking a serene coastal landscape.

Cottage in Kula

Oceanview Cottage away from heat! w/ County Permit

Closest Airbnb listing to the Haleakala National Park and Road To Hana. Away from 100 degree heat & traffic & noises & yet still close to restaurant, cafe and market! 100% Private Cottage on 2acres of orchard on Haleakala, with 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. Approved by Maui County w/ short term rental. The permit #s are listed in the license section.

5 out of 5 average rating, 27 reviews

A charming retreat is nestled in a natural setting, surrounded by lush greenery and mountains. The structure features a distinctive green roof, with warm lights glowing from windows. A cozy seating area is visible on the porch, inviting relaxation amid serene surroundings.

Cottage in Wailuku

Romantic and Private Cottage and Gazebo for two!

Romantic, Private, a Sanctuary, beautifully decorated, local charm and sleeping to the sounds of Wailuku River are a few things our guests say about our Inn. An American Whirlpool hottub is our newest feature amenity along with the air conditioning, washer/dryer, full kitchen and a large shower in your private bathroom. A king Size bed, Wifi, barbeque grill, television, fans beach towels are standard amenities. The detached Gazebo is perfect for reading, meditating, or just doing nothing!

4.98 out of 5 average rating, 57 reviews

The cottage exterior presents a light green facade with a sloped roof, complemented by vibrant flowering shrubs. A private carport is visible beside the entrance, and a shaded seating area is provided under an umbrella on the porch. The scene is surrounded by lush greenery.

Cottage in Wailea

Maui Meadows Ocean View Cottage

Our 1 bedroom Ocean view cottage offers the maximum in privacy and convenience. Located in Sunny South Maui, just above the Wailea Resort, our cottage has everything you need to Maui Maui your Home. AC, WiFi, Fully equipped kitchen, covered carport and more... We are a Maui County permited B&B and our quoted price will include Hawaii State and Maui County taxes of 17.42%. Be sure to always confirm if your rental is permitted and if tax is included in the price quoted.

Superhost

A welcoming living area features a light-filled space with an open layout. A dining table with two chairs is set for meals, while a comfortable sofa sits next to a large window showcasing outdoor views. Vibrant orange curtains complement the neutral tones of the room.

4.8 out of 5 average rating, 93 reviews

Romantic Suite | Tropical Escape | BBQ & Hot Tub

• Perfect for couples—Queen bed and romantic ambiance • Outdoor hot tub, BBQ, and tropical vibes • Prime location in Kihei—just minutes from restaurants, bars, coffee shops, and groceries • Quick access to top spots: 15 mins to Wailea, 1 hr to Haleakalā, 2 hrs to Hana Sleep on Maui Cottage: 1 Bed Honeymoon Jacuzzi Penthouse • Backyard amenities shared with our Sleep on Maui House. Contact us to discuss rates and options for groups up to 8!

A charming cottage is set amidst lush tropical foliage, featuring a well-maintained path leading to a white staircase. Green plants and trees frame the entrance, creating a serene and private environment for guests.

4.97 out of 5 average rating, 123 reviews

One Block to the Beach! Cozy Beach Cottage Kihei

Welcome to Chez Maui! This cozy 2-bedroom, 1-bathroom cottage is just one block from the beach, offering a peaceful and private retreat. Perfect for your vacation or for remote workers, traveling healthcare professionals, snowbirds or those in transition to longer-term accommodation. The cottage comfortably hosts up to 4 guests maximum and has been recently renovated. *Make sure to turn on your notifications for Airbnb Messaging.*

4.99 out of 5 average rating, 213 reviews

A scenic view captures the sunset over a lush landscape, with a pool reflecting the colorful sky. Tall trees frame the scene, and the distant ocean is visible beneath the dramatic clouds. The vibrant greens of the surrounding vegetation provide a serene backdrop.

Cottage in Makawao

Rustic Upcountry retreat with breathtaking views!

Maui County Permits BBMP2019/0006 & SUP2 2019/0003 This is a BnB not a STRH Owners live on property At this time we are hosting to guests 12 or older. This property is terraced so not optimal for young children. This is a non smoking property. No smoking is allowed. Use of the pool, hot tub and dry sauna are private when reserved with our private calendar. Mahalo!

4.96 out of 5 average rating, 25 reviews

A serene swimming pool is framed by lush tropical vegetation and tall palm trees. A waterfall cascades down a rock formation into the pool, while a waterslide is visible on the side. The sky above is bright with scattered clouds.

Cottage in Wailea

Private 2 bedroom cottage with pool

Hale Manu mele the perfect Maui vacation.Hale Manu Mele B&B permit #BBKM2013/0001.Tat # TA-031-786-3936-01. We are a legal B&B in Maui The 720 Sq feet cottage is a beautiful newly remolded 2 bedroom 1 bath cottage nestled on a shared 1/2 acre. You'll find an open floor plan with Koa wood floors to granite counters and a beautiful pool to enjoy.

A serene sunset is depicted over the ocean, with vibrant hues of orange and yellow radiating from the setting sun. Rays of light extend outward from the sun, casting a gentle glow across the water's surface, creating a tranquil coastal scene.

5 out of 5 average rating, 5 reviews

Grateful Casita

Welcome to our cozy casita! This peaceful one-bedroom, one-bath cottage is perfect for solo travelers or couples seeking an intimate getaway. Located in a quiet neighborhood with your own private entrance, you'll have a fully equipped kitchen and comfortable living space to unwind after exploring the island.

4.96 out of 5 average rating, 212 reviews

A spacious bedroom is furnished with a comfortable king bed and a queen sofa sleeper. A dresser with a mirror stands nearby, accompanied by a small glass table. Light green walls complement the decor, while natural light filters through the window featuring blinds.

Cottage in Wailuku

Newly Renovated Modern Cottage; Walk into Town!

Brand new, freshly renovated, permitted & legal. Private entry & parking in front of entry. If you were looking for a great deal in Central Maui, you’re in luck as the rates offered for those who book now are very competitive to welcome you to get away to one of the safest places to escape in the world!

4.96 out of 5 average rating, 371 reviews

The exterior of a modern home is displayed, featuring a large wooden deck surrounded by lush tropical plants and flowers. The structure has a gabled roof, multiple windows, and a welcoming entrance. A gravel pathway leads to the steps of the deck.

Cottage in Kula

HALEKALANI - Paradise in Upcountry

Beautifully designed custom home in Upcountry Kula with panoramic views of the coasts, West Maui mountains, and neighbor islands. The perfect location for peaceful relaxation while you enjoy your stay in Maui and everything it has to offer. County of Maui Permit #BBMP 2015/0006, SUP2 2015/0005

A single-story cottage is surrounded by a lush tropical garden, featuring vibrant flowers and palm trees. A spacious green lawn invites relaxation, while the wooden deck area, partially shaded, offers a welcoming space for outdoor activities.