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Vacation rentals in Kahakuloa

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Top-rated vacation rentals in Kahakuloa

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Top guest favorite
The image captures the exterior of Villa 1615, set within a lush green landscape. Palm trees and other tropical plants surround the two-story villa, which features multiple balconies. The expansive ocean view is visible in the background, highlighting the natural beauty of the location.
Townhouse in Kapalua
4.96 out of 5 average rating, 223 reviews

Spectacular views, prime location Kapalua, Maui.

Stylish, romantic two-level villa enjoying spectacular direct views of the Ocean. Relax and rejuvenate on the upstairs BR private lanai or the ground floor patio both are ideal for viewing the stellar coastal landscape. Start the day by watching the sunrise over the ocean from the comfort of your luxurious California King bed. Walking distance to everything that makes Kapalua Resort a special, magical and unforgettable place. A/C units on both levels. Kapalua is unaffected by the Lahaina fire

Guest favorite
The image captures a resort pool surrounded by tropical palms and vibrant greenery. A view of the ocean and distant mountains is visible, with lounge chairs positioned around the pool area. Gentle waves can be seen lapping at the beach in the background.
Condo in Lahaina
4.86 out of 5 average rating, 166 reviews

Aloha, Ocean View 1 bed Papakea Spring Specials

ALOHA, welcome guests to our Ocean View 1 bedroom condo and Ocean Front property at Papakea Resort. Enjoy all Maui has to offer. Everything you need for your vacation in our Beautiful Ocean View Condo. King Size Bed, complete kitchen, washer/dryer. Lanai with high top table and ocean view from the 2nd floor, corner unit. Ceiling fans and a/c. Papakea is a beautiful property on the ocean. Great sunset. Water aerobics, yoga, Mai Tai Party, Lei Making, Pickleball Walk to restaurants stores.

Top guest favorite
An expansive covered lanai features comfortable seating with plush cushions, accented by a decorative table. String lights adorn the ceiling, and panoramic ocean views showcase a vibrant sunset over palm trees and neighboring properties.
Guest suite in Wailea
4.99 out of 5 average rating, 134 reviews

Sweeping Panoramic Ocean Views - Private Ohana

Live like a local at the Ocean Blue Ohana - the private first floor of this amazing Hawaiian pole home on a half acre property in South Maui. As you enter the space, you will be drawn to the sweeping panoramic ocean views. You are sky-high, perched 500 feet above sea level, looking at the most glorious views of the neighboring islands, mountains, coastline, and Maui's amazing skyline. To top it off, you are 5 minutes from the Wailea Resorts and beautiful golden sand, crystal clear beaches.

Top guest favorite
The exterior of a private cabin is surrounded by lush greenery, featuring vibrant tropical plants. A porch with rocking chairs offers a welcoming spot to relax. The cabin's distinctive architecture includes a sloping roof and decorative wooden details, providing a harmonious blend with the natural environment.
Farm stay in Haiku
4.97 out of 5 average rating, 317 reviews

Ocean View - Private Cabin

NOTE: Many oceanfront condominiums are currently under threat of a phase-out. Farm stays are a "Permissible Use" on agricultural bona fide farms by State of Hawai'i law. Be assured your reservation here will be safe from government interference. Located on a working coffee plantation and food forest, this restored cabin is private but close to lots of upcountry activities. Kitchen, ocean view, open concept, great lanai spaces, plenty of off-street parking, access to private hiking trails.

Guest favorite
A modern living space features a comfortable sofa and a wooden coffee table. A wall-mounted TV displays a tranquil beach scene. Expansive glass doors lead to a balcony with ocean views, surrounded by tropical greenery. Natural light enhances the neutral tones of the decor.
Condo in Kihei
4.99 out of 5 average rating, 148 reviews

Sea-rene & Tropical Views

Newly remodeled oceanfront 1 bedroom, 1 bath condo with fantastic ocean views. Located in the sunny and vibrant beach town of Kihei. Beach chairs, umbrellas, luxury beach towels and a cooler are all provided to enjoy your day at the beach! We strive to achieve a welcoming and thoughtful retreat for your stay in magical Maui. Whether you dine out at one of the delicious restaurants nearby or play chef in our fully stocked kitchen, you will enjoy your new home away from home in Maui.

Guest favorite
An open concept living space is displayed, featuring a comfortable leather sofa and a wooden dining table. Large sliding glass doors invite natural light, while a modern kitchen is visible in the background. Ceiling fans and decorative elements enhance the airy ambiance.
Farm stay in Haiku
4.94 out of 5 average rating, 433 reviews

Kalani at Haiku Garden Cottages Farm Sanctuary

Welcome to Haiku Garden Cottages, a licensed Farmstay and B&B on Maui’s North Shore (Permit #BBPH2017/0002). Kalani is a charming cottage where you can sip coffee on the lanai, wander garden paths, harvest seasonal fruit, and settle into island rhythms. Enjoy ocean and garden views, a private outdoor shower, and relaxed indoor-outdoor living—just minutes from Haleakalā, the Road to Hāna, beaches, hiking trails, restaurants, and farmers markets.

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, 208 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

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, 106 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 panoramic view showcases lush green landscape merging into the blue ocean on the horizon. A variety of trees, including a tall conifer, adds to the natural beauty. The sky is bright with scattered clouds, creating a serene atmosphere.
Home in Haiku
4.99 out of 5 average rating, 196 reviews

Charming Hoku Pauwela Breathtaking ocean views!

Located on the north shore of Maui, Hoku Pauwela (Maui County B&B Permit# BBPH 2019/0002 and Hawaii State TAT # TA-036-968-8576-01) is the ideal location from which to experience the north shore, upcountry, Haleakala crater, and the epic drive to Hana. Spacious, quiet, and family-friendly, you'll have all you need to explore Maui and a peaceful living area to relax in after a day of adventuring.

Top guest favorite
An outdoor deck is surrounded by lush greenery, featuring wooden flooring and multiple seating options. Two wicker chairs and a low table are positioned for relaxation, while a central fire pit adds a gathering point. Landscape elements create a serene environment for outdoor enjoyment.
Guest suite in Kula
4.99 out of 5 average rating, 304 reviews

Kula Jacaranda Studio on the Slopes of Haleakala

Kula Jacaranda studio is reached by a treehouse walkway. Your private covered deck offers a place to dine and watch the sunset . The shared barbecue area offers a place to prep your own meals. We provide coffee, tea, oil, vinegar and salt. The luxurious walk-in shower offers double shower heads and benches. With years as AirBnb super hosts, we've got everything you need.

Guest favorite
Lush tropical greenery is visible, featuring tall palm trees swaying gently in the breeze. The vibrant landscape leads to an expansive view of the ocean, where the water meets the sky in the distance. A serene, rolling lawn invites relaxation.
Bungalow in Hana
4.91 out of 5 average rating, 209 reviews

Ala Type Ocean Vista - Hana Bed & Breakfast

Ala Aina Ocean Vista is a private ohana with its own private front and back entrances. It is situated on an old banana plantation located on an exotic, lush, tropical property. It provides guests with peace & quiet and offers gorgeous vistas of tropical trees, flowers, rolling green lawns and sweeping ocean views in the distance. Permit BBHA2013/002 SUP2-2001/0016

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, 231 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 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!

Popular amenities for Kahakuloa vacation rentals

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  2. United States
  3. Hawaii
  4. Maui County
  5. Kahakuloa