Cottage vacation rentals in Lahaina

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Top-rated cottage rentals in Lahaina

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Top guest favorite
An intricately carved wooden front door is framed by two decorative pedestals, each featuring a plant arrangement that includes tropical foliage. The entrance is highlighted by a welcome mat on a wooden deck, exuding a warm and inviting entryway.
Cottage in Haiku
4.99 out of 5 average rating, 88 reviews

Ho'okipa Rose - Peace and Serenity

E Komo Mai! Ho'okipa Rose, Peaceful, Tropical home in the quaint town of Haiku. Lovely 2 bedroom, 2 bath, 1000 sq. ft. cottage located on private, two acre property. Fully equipped kitchen with everything you need to prepare meals. Upscale amenities throughout. Outdoor shower and infrared sauna. Beach chairs, towels, boogie boards and other beach items. 5 minutes from the famous Ho'okipa & Jaws! 10 minutes from the charming town of Paia and beaches. Enjoy Maui away from the busy touristy areas.

Guest favorite
An open kitchen and living area is highlighted by a sleek countertop and warm wooden cabinetry. Large windows offer views of the ocean and beach, while a comfortable seating nook enhances the space. Natural stone flooring adds texture to the room.
Cottage in Kaanapali
4.83 out of 5 average rating, 46 reviews

OCEAN VIEW Kaanapali Cottage ICC 24

OCEAN VIEW top of the property adjacent to the 12th fairway of the Royal Kaanapali Golf Course. This Kaanapali Cottage with 2 beautiful swimming pools is a mere 5 minute walk from the local favorite "Airport Beach", featuring world-class snorkeling & miles of pristine white sand beach's. There is a beachfront boardwalk & paths for walking, exercising in both directions accessing shopping (Whalers Village) & restaurants. ITS A PERFECT PLACE FOR ANYONE WANTING TO GET AWAY WEEKLY DISCOUNT

Top guest favorite
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
4.96 out of 5 average rating, 429 reviews

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.

Top guest favorite
An inviting outdoor living area features wooden seating arrangements adorned with plush cushions. Lush greenery surrounds the space, and decorative string lights create a warm ambiance overhead. A shaded daybed offers a comfortable spot for relaxation amid the tropical landscape.
Cottage in Lahaina
4.93 out of 5 average rating, 147 reviews

Kaanapali Cottage ICC 29 Indoor/Outdoor Living

International Colony Club’s cottage 29 is located in the world-famous Kaanapali Beach area, and a five minute walk from one of Maui’s best beaches. Built in 1964, this community affords a spacious and mature landscape between 44 private cottages spread over 10 acres. Our Hawaiian plantation style cottage is reminiscent of homes built during the plantation era and conveniently located close to beaches, shopping and restaurants, but is secluded from the hustle and bustle of the big resorts.

Guest favorite
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
4.92 out of 5 average rating, 52 reviews

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.

Top guest favorite
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
5 out of 5 average rating, 32 reviews

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!

Top guest favorite
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.
Cottage in Kihei
4.97 out of 5 average rating, 126 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.*

Top guest favorite
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.
Cottage in Kihei
5 out of 5 average rating, 13 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. 🙏🏡

Top guest favorite
A view from the property features a terracotta-tiled roof in the foreground, framed by lush green foliage. In the distance, the vast blue ocean is visible, along with the silhouettes of neighboring buildings and gently swaying palm trees against a backdrop of rolling hills.
Cottage in Lahaina
4.96 out of 5 average rating, 107 reviews

Charming Kaanapali cottage with ocean view

A charming "Old Hawaii" bungalow on lush landscaped tropical grounds, only a ten minute walk from Kaanapali Beach, the best beach in West Maui. Close to numerous restaurants and shops in the Kaanapali area. But so beguiling is the view of Lanai and Molokai islands as you drink your morning coffee, so inspiring the sunsets as you sip your cocktail in the late afternoon--you may never leave the lanai!

Top guest favorite
The exterior of a cottage is shown, featuring a mix of light and dark pink siding. Solar panels are installed on the roof. Lush green landscaping surrounds the property, with palm trees and bushes enhancing the tropical ambiance. A concrete driveway leads to a covered entryway.
Cottage in Haiku
4.98 out of 5 average rating, 101 reviews

Leilani's "Leimomi" Cottage - County Licensed

Maui County License: STPH2013/0020 (taxes are included in rate) The home is part of the county licensed Leilani vacation rental property. The cottage is about 650 square feet with open beam ceiling and lots of windows and sliding doors with ocean views. Other amenities are a king size bed, full kitchen, outside covered sitting area with Jacuzzi , BBQ and lawn chairs.

Top guest favorite
A quaint blue cottage is surrounded by lush greenery and vibrant red tropical plants. Large windows reflect the natural light, and the front porch invites relaxation. The well-maintained lawn complements the charming exterior, enhancing the cottage's appeal in its serene setting.
Cottage in Haiku
4.95 out of 5 average rating, 275 reviews

Great Location, 1 BR Beachy, VERY CLEAN Cottage

COUNTY PERMITTED - This home holds legal Maui Permit STPH2015/0006. Amazing Haiku location, Very Clean, Cute Beachy-style, 1BR/1BA cottage home. 1 Queen bed very comfortable, quick walk to Haiku Grocery, Haiku Cannery, Nuka Sushi, Haiku Mangala Yoga, Colleen's, Short 4 mile drive to Ho'okipa, (sleeps 1-2) well equipped kitchen & new appliances

Top guest favorite
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
4.96 out of 5 average rating, 377 reviews

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

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