Cottage vacation rentals in Wailea

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Top-rated cottage rentals in Wailea

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Guest favorite

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

4.96 out of 5 average rating, 210 reviews

★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 ✔

Top guest favorite

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

5 out of 5 average rating, 108 reviews

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

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

4.92 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.

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, 24 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!

Guest favorite

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

4.98 out of 5 average rating, 55 reviews

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.

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

4.95 out of 5 average rating, 386 reviews

Oceanview Cottage away from heat! w/ County Permit

Closest to the very top 2 Maui attractions (Hana and Haleakala) and away from 100 degree heat & traffic & noises & yet still close to everything! Private Cottage on 2acres of orchard on Haleakala, 1 mile from Kula Lodge, w/ endless pano Bi-Coastal View (Double Ocean View that no other islands have) & night city view! Stunning sunset & starry nights. Approved by Maui County w/ short term rental. The permit #s are listed in the license section.

Guest favorite

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.

Cottage in Haiku

4.83 out of 5 average rating, 215 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.

Top guest favorite

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.

Cottage in Haiku

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

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, 120 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.*

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, 101 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

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

4.99 out of 5 average rating, 208 reviews

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!

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, 254 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