Cottage vacation rentals in Makena

The exterior of a renovated cottage is displayed, featuring a spacious lanai with patio furniture shaded by an umbrella. Lush greenery and colorful flowers frame the entrance, enhancing the tranquil setting. Large windows invite natural light into the interior space, showcasing an inviting atmosphere.

5 out of 5 average rating, 55 reviews

Beautiful Beach Cottage: lush garden paradise

A private, clean & beautifully renovated 2 bdrm cottage w its own garden just off the ocean (Kalama Park) in Kihei & walking dist to beaches, tennis courts, snorkeling, supermarket, movies, restaurants, skate park, surfing, kiting, windsurfing, library & more. Enjoy an independent cottage & outdoor space of your own in a local, oceanfront neighborhood with a quiet and private charm. One of a small # of legal short term Maui rental cottages: BBMK2019:003 TA/GE Tax ID Number: TA/GE-013-759-6928-01

4.95 out of 5 average rating, 447 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 to Haleakala National Park & Road To Hana. Away from 100 degree heat & traffic & yet still close to food & market! Private Cottage on 2acres of orchard on Haleakala, w/ 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. For past guests whom love this home, this AirBnB ends on 12/31/26. Hawaii Supreme Court ruled no more short term rental in agriculture lands.

4.98 out of 5 average rating, 58 reviews

Cottage in Wailea

Private Ocean View Cottage Near Wailea - Sunsets

Wake up to birds chirping, tropical gardens and ocean views. Our private 1 bedroom Maui Meadows Ocean view cottage in Sunny South Maui is just above the Wailea Resort, with world class beaches, golfing, snorkeling and dining. Our cottage has everything you need to make Maui your Home. AC, WiFi, Fully equipped kitchen, washer/dryer, covered carport and more... We are a legally permited B&B. Be sure to always confirm if your rental is permitted to operate in Maui.

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.

4.81 out of 5 average rating, 101 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, 130 reviews

Cozy Beach Cottage in Kihei BBKM 2018/0002

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.*

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, 15 reviews

Grateful Casita

Welcome to Grateful Casita — a well-loved local home with driveway, private yard, and quiet neighborhood. Real local living, upgraded with a king sized bed! 🛏️😴 Nestled beneath Maui's blue sky, wrapped in lush tropical greenery — this humble Casita is small in size but enormous in heart. Your own soft place to land. 🛬 May your good energy, warm aloha, and peaceful moments find your way to our humble Casita. 🙏🏡

4.99 out of 5 average rating, 237 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, 27 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.

4.96 out of 5 average rating, 385 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.