Cottage vacation rentals in Wailea, Wailea-Makena

4.97 out of 5 average rating, 202 reviews

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 ✔

4.8 out of 5 average rating, 40 reviews

A tropical landscape surrounds the cottage, featuring a large flowering tree with white blossoms. Lush greenery and well-maintained shrubs add to the natural beauty, providing a serene atmosphere. The cottage's exterior complements the vibrant surroundings, inviting relaxation in a peaceful setting.

Cottage in Lahaina

Kaanapali Cottage ICC24 ocean view- House for rent

A GEM IN THE MIDDLE OF THE PACIFIC sitting right on the Kaanapali golf course, this ocean view Maui Cottage with 2 beautiful swimming pools is a mere 5 minute walk from the local favorite "Airport beach", featuring world-class snorkeling and miles of pristine white sand beach's. There is a beachfront boardwalk and paths for walking, exercising in both directions accessing shopping (Whalers Village) and restaurants. ITS A PERFECT PLACE FOR ANYONE WANTING TO GET AWAY. WEEKLY DISCOUNT

4.99 out of 5 average rating, 190 reviews

A modern kitchen features sleek white cabinetry and stainless steel appliances, with an island bar seating area highlighted by four rattan stools. Pendant lights hang from the ceiling, illuminating the space. A potted orchid adds a touch of greenery to the counter.

Cottage in Haiku-Pauwela

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! The cottage can accommodate 2 adults and 2 children. 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

4.96 out of 5 average rating, 47 reviews

A traditional cottage is framed by lush green grass and vibrant tropical plants. Brightly colored flowers add splashes of color to the exterior. Palm trees rise against a blue sky, casting gentle shadows on the inviting path leading to the entrance.

Cottage in Lahaina

CLASSIC HAWAIIAN COTTAGE

This cottage is located in a beautiful, quiet associated neighborhood(quiet time 9pm-8am). It is within walking distance of some of the island’s best beaches Maui has to offer! Whaler’s Village Shopping Center, golfing and fine cuisine are a short cab ride or walking distance from the cottage! The 5 minute walk to watch the sunset on the beach is well worth it. In fact, some do this every single night. Are you tired of astronomical taxes and resort fees? They are all included in our rate.

4.73 out of 5 average rating, 22 reviews

Lush tropical landscaping surrounds the pathway leading to the cottage. Various green plants and palm trees create a private and serene outdoor space. A small building is visible in the background, contributing to the inviting atmosphere of the garden.

Cottage in Paia

Walk to small beach, charming cottage

STPH2013/0010 A charming vacation rental cottage in Paia / Kuau on Maui’s well-loved North Shore. 15 minutes from Kahului airport and centrally located to many Maui attractions, such as the sunrise from Haleakala or driving the beautiful winding road to Hana. We are very close to the trendy, historic town of Paia, with restaurants, galleries, boutiques and more. The cottage is a stroll away from the Kuau Store deli and the #1 rated beachfront restaurant on Maui, Mama’s Fish House.

4.98 out of 5 average rating, 51 reviews

A well-maintained wraparound deck features comfortable seating under a striped umbrella. Lush tropical landscaping with vibrant flowers surrounds the space, enhancing the natural beauty. A grill is positioned adjacent to the seating area, providing an inviting space for outdoor dining.

Cottage in Kihei

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.

4.92 out of 5 average rating, 222 reviews

A view of the lush garden is captured, showcasing a variety of tropical plants and trees. In the distance, structures blend harmoniously with the greenery, while the sky is adorned with scattered clouds, enhancing the tranquil atmosphere of this private retreat.

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. Hot Tub. 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

4.95 out of 5 average rating, 358 reviews

Cottage in Kula

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.

4.83 out of 5 average rating, 86 reviews

Cottage in Kihei

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!

4.82 out of 5 average rating, 203 reviews

Cottage in Haiku-Pauwela

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.

4.99 out of 5 average rating, 196 reviews

The spacious bedroom features a large bed with white linens and green accents. A tray with a candle is placed on the bed. Floor-to-ceiling windows offer a view of the sunset, while a cozy seating area with two chairs is visible on the balcony.

Cottage in Makawao

Luxury 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!