Cottage vacation rentals in Paia

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.

4.99 out of 5 average rating, 86 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.

4.96 out of 5 average rating, 210 reviews

An aerial view highlights the cottage nestled among lush greenery, showcasing solar panels on the roof. A private hot tub is set near outdoor loungers, with stone pathways leading through the vibrant tropical landscape.

Cottage in Maui

★Haleakala Cottage - PRIVATE HOT TUB, POOL ACCESS

Come enjoy the ultimate Hawaiian oasis nestled in the corner of our lush tropical gardens and organic homestead. Haleakala Cottage is the perfect place to relax and unwind. Enjoy a chilled glass of wine in your own private hot tub and gaze up at our beautiful stars - the perfect romantic honeymoon hideaway! ★Jump Start to The to the Road to Hana! ✔ ★NEW CENTRAL AC ✔ ★Private Hot Tub ✔ ★44 ft Swimming Pool (shared) ✔ ★King Bed ✔ ★Outdoor Shower✔ ★Sunrise View ✔ ★Cliff Walk ✔ ★Full Kitchen ✔

5 out of 5 average rating, 109 reviews

The entrance to the cottage is framed by a large tree and lush greenery, providing a welcoming appearance. Stone steps lead up to the front porch, which is adorned with a small seating area. The surroundings feature a gravel road and neighboring homes.

Cottage in Paia

LunaHouse In The Heart of Paia

Thoughtfully refurbished / modernized c.1934 plantation cottage in central Paia Town. Steps away from beach, restaurants, bars, grocery, boutiques. 832 SF; Amenities including: Ceiling Fans; A/C; Outdoor shower, Large 26cf fridge w/ ice-maker, Micro-hood, Dishwasher, oven and induction cooking pads, LG laundry; Wifi Internet: 200mbs; Max occupancy is 4 Guests (Including children & infants). Office room w/ desk, ergonomic chair. BBQ area w/ sink; Fridge, Propane grill. Maui Permit: BBPH

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.

4.92 out of 5 average rating, 140 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.

4.95 out of 5 average rating, 397 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.

4.91 out of 5 average rating, 231 reviews

A spacious yard surrounds a detached cottage, featuring a large tree providing shade. Lush greenery and tropical plants are visible throughout the property. A pathway leads from the yard towards the cottage, which has large windows and an inviting entrance.

Cottage in Maui County

Ualani Retreat. Private Ocean View Cottage.

Private Detached stand alone cottage home on 3 acre retreat. Beautiful ocean and mountain views. Lush Haven surrounded by fruit trees and bamboo groves. Nicely equipped kitchen. Laundry room. Cable TV. Wi-Fi. Delightful Island Home. Very Comfortable. Close to enjoy some of Maui's best attractions - Haleakala Volcano, Road to Hana, Waterfalls & Baldwin Beach. Locally Owned & Occupied B&B PERMIT : BBPH 2012/0002 SUP2 2012/0001

A distinguished bamboo cottage is elevated on stilts, surrounded by lush tropical vegetation. Wooden decks wrap around the structure, providing access to outdoor seating areas. Large windows offer views of the surrounding greenery, harmonizing the indoor and outdoor environment.

4.83 out of 5 average rating, 216 reviews

Hawaiian DreamTemple- Tropical Oasis BBPH20120004

Welcome to your "Hawaiian Dream Temple" [PERMIT- BBPH2012-0004] [TMK (2) 2-7-029: 015-0000] Our tropical bamboo 2 bedroom - 1 bathroom temple is a private house that invites you to true Maui. We are in a quiet area in upcountry, Haiku away from the hotels. You can experience the little sanctuary and hidden paradise that still exists, close to Hana and Haleakala crater. It is surrounded by tall trees, tropical flowers and lush vegetation.

An outdoor dining area features a wooden table surrounded by six cushioned chairs. Lush greenery and palm trees frame the view, while the distant ocean is visible under a clear sky, creating a serene space for al fresco meals.

4.99 out of 5 average rating, 200 reviews

North Shore Ocean View Cottage

This recently built comfortable cottage is located on the north shore of the island of Maui, tucked away in the quiet countryside of Haiku but relatively close to major attractions! Enjoy a relaxing vacation in a rich tropical setting with spectacular ocean views! Please Note: State of Hawaii Maui County adds 17.96% tax to your guest fees. TA-060-126-6176-01 GE-060-126-6176-01 BBPH 2016/0001 SUP 2 2015/0008

4.97 out of 5 average rating, 121 reviews

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

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.*

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.

4.96 out of 5 average rating, 103 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!

4.99 out of 5 average rating, 212 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. Aloha, sorry but at this time we are not hosting to families with children younger than 16 at this time. 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!

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.

4.95 out of 5 average rating, 259 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

Popular amenities for Paia cottage rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

A private cottage is nestled among vibrant tropical foliage along a gravel path. Lush greenery surrounds the home, showcasing a blend of colorful flowers and palm trees. The cottage features a welcoming porch, perfect for enjoying the serene garden views.

5 out of 5 average rating, 12 reviews

Privacy, Luxury, Ocean View Cottage, HotTub, K-Bed

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.

5 out of 5 average rating, 26 reviews

Romantic and Private Cottage and Gazebo for two!

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.

Cottage in Kihei

4.8 out of 5 average rating, 92 reviews

Romantic Suite | Tropical Escape | BBQ & Hot Tub

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.

4.98 out of 5 average rating, 94 reviews

Leilani's "Leimomi" Cottage - County Licensed

Pet-friendly cottage rentals

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.

4.94 out of 5 average rating, 36 reviews

3B/2B FamilyVacationComfort HawaiianaCharm Central

5 out of 5 average rating, 5 reviews

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

Grateful Casita

4.98 out of 5 average rating, 56 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

4.96 out of 5 average rating, 210 reviews

Cottage in Maui

★Haleakala Cottage - PRIVATE HOT TUB, POOL ACCESS

Private cottage rentals

Superhost

Cottage in Paia

4.75 out of 5 average rating, 24 reviews

Walk to small beach, charming cottage

An airy living space is depicted, featuring a comfortable sofa, a dining table with chairs, and a kitchenette area. Natural light filters through jalousie windows, creating a relaxed atmosphere. A ceiling fan gently circulates air, and a door leads outside to a private area.

4.63 out of 5 average rating, 129 reviews

Cute Plantation Cottage; Walk into Wailuku Town!

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

4.81 out of 5 average rating, 43 reviews

OCEAN VIEW Kaanapali Cottage ICC 24

A modern kitchen features a large island with a granite countertop, complemented by four striped barstools. Under-cabinet lighting highlights the backsplash, while pendant lights hang overhead. Cabinets and a refrigerator are positioned against the wall, with a view of greenery visible through the open door.

Beautiful Cottage 5 Minutes From Beach

This bedroom features a spacious bed adorned with a floral quilt and light wood accents. Two bedside lamps provide soft lighting, and a wooden dresser complements the room. Large windows with sheer curtains allow natural light to fill the space, which has warm wooden flooring.

4.61 out of 5 average rating, 213 reviews

Renovated Plantation Home; Walk into Wailuku Town!

Superhost

A charming entrance is framed by vibrant pink bougainvillea, contrasting against the muted green exterior of the cottage. A stone pathway leads to the door, accentuated by a small patio area, while lush grass provides a natural setting.

5 out of 5 average rating, 3 reviews

Maui -Kaanapali - International Colony Club

A landscaped backyard features lush green grass and decorative plants. A glass-top table is surrounded by four light-colored chairs, offering a space for outdoor dining. A barbeque is partially visible, and a wooden fence encloses the area, providing privacy.