Holiday rentals in Olowalu

4.98 out of 5 average rating, 215 reviews

Guest house in Kula

Upcountry Alpaca, Llama, and Rabbit working farm

Experience Maui's first working fiber farm, home to Alpacas, Llamas, and Angora rabbits. Sitting at 3300 ft above sea level, Cottontail Farm enjoys perfect weather days and crisp, cool nights. The cooler temperatures are perfect for our wool producing animals that graze just outside your cottage in the back yard. Our alpacas and llamas are quiet observers but also provide plenty of entertainment of their own. Our group of Angora rabbits can be seen out the window hopping around their enclosures.

4.97 out of 5 average rating, 213 reviews

Cabin in Maui

★Rainbow Lookout - PRIVATE HOT TUB+ACCESS TO POOL

This Stunning North Shore Maui hideaway is surrounded with lush fruit and flower gardens, coconut palms, banana trees, and has easy access to all there is to do on this magnificent island. Stargaze … soak in your own private hot tub with a chilled glass of wine and enjoy a once-in-a-lifetime experience. The 'real' Maui:)! ★Jump Start to The to the Road to Hana! ✔ ★New Cold Central AC ✔ ★Cliff Walk ✔ ★Ocean View✔ ★Private Hot Tub ✔ ★44 ft Swimming Pool ★King Bed ✔ ★Sunrise View✔ ★Star Gazing✔

4.99 out of 5 average rating, 131 reviews

Home in Makawao

Private Luxurious Cottage

This marvelous accommodation is for the nature-lover who enjoys luxury. It boasts a lovely deck which looks out onto majestic tall trees and lush green foliage with a romantic soaking tub for two. Centered in the room is a custom-made king-size bed fashioned from cherry wood and adorned with luxurious bedding. There is full kitchen and dining area with views for a tranquil place to share a meal. This is true Hawaiian style where you can enjoy comfortable, elegant and laid-back island living.

4.99 out of 5 average rating, 122 reviews

NEWLY REMODELED OCEAN VIEW CONDO, STEPS FROM BEACH

Your next relaxing Lahaina escape awaits at this stunning 1-bedroom, 2-bath vacation rental condo - steps away from Kapalua Bay Beach & centrally located next to the Montage Resort. Your group of up to 6 guests will love returning to the comfort of this home, offering over 1,100 sq ft of living space. With easy access to championship golf courses, fine dining, walking/hiking paths, shopping, spas, & several bays/beaches great for snorkeling, surfing, & relaxing, this is the perfect home base.

4.92 out of 5 average rating, 117 reviews

Apartment in Kihei

40% off ! Oceanfront Views in the heart of Kihei

40% off nightly rates during construction. Are you the kind of travelers who get up early and get going? This can be a great opportunity for you. Construction hours 8am-4pm. No construction on weekends or holidays. Noise ranges from spotty to very loud. Pano ocean views from this beautifully updated, fully air-conditioned condo. A guest favorite, it's a 2-minute walk to Kalama Beach Park and Cove Beach. Easy self-checkin, then a 2-3 minute walk to food trucks, bars, restaurants and shopping.

4.99 out of 5 average rating, 112 reviews

Guest suite in Wailea

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.

4.99 out of 5 average rating, 124 reviews

Luxury Mahana 1bd/2ba-Great Views-Free Park/WiFi

Locally Owned and Operated 1BD/2BA condo with the best direct beachfront location, panoramic Ocean views, sunsets, and seasonal whale watching. The owner’s spared no expense in renovating this unit making it hand’s down one of the nicest units in all of the Mahana. Wake up to the cool tropical breeze and sounds of the shoreline just 50 feet away. Floor to ceiling windows in the living area and bedroom bring the stunning views and warm Maui sun inside while central AC keeps you cool inside.

4.92 out of 5 average rating, 1,074 reviews

Flat in Kula

Kula Treat - Upcountry Maui with Hot Tub!

Private, gracious apartment in desirable Upcountry Maui. Great home base for exploring, and a quiet country retreat for relaxing. Restaurants, food trucks and farmers’ markets nearby. Beaches, hiking and zipline within an easy drive. Perfectly located for Haleakalā Natʻl Park and day trips to Hana. A wonderful personal chef lives very close by. Dedicated to reducing single use plastics, we provide reusable water bottles for our guests! Fully permitted: BBMP 2015/0003 E komo mai! (Welcome)

4.96 out of 5 average rating, 108 reviews

Apartment in Wailuku

Oceanfront Getaway, Brand New, Steps To Beach

Enjoy the panoramic ocean view directly from the living room. This wonderful ground floor unit offers privacy and tranquility with expansive ocean views, where you can enjoy seasonal whale watching, paddle boarding, surfing, snorkeling as well as many other activities just outside your door. The unit is also adjacent to one of the longest beaches on Maui, Sugar Beach. And just down the road you will find great shopping, restaurants, nightlife and the Maui Ocean Center.

4.98 out of 5 average rating, 133 reviews

Kapalua, luxe, ocean view, beach, spa, golf/tennis

KAPALUA - Best location! Welcome to the luxuriously Kapalua Bay Villa #37B1. Bright and airy, with comfortable furniture and modern appliances. Scenic ocean view, a 5-minute walk to Kapalua Bay, Montage Resort, tennis, golf, hiking, zip-lining, amazing restaurants, and a first-class spa. Kapalua Bay Villas is a low-density community within the Kapalua Resort—a 15-minute drive to Kaanapali, and a 40-minute drive to Central Maui to explore the island.

4.91 out of 5 average rating, 241 reviews

Villa in Wailuku

Luxurious 1BR Near I'ao Valley, Bright and Modern!

Experience authentic Maui at The Blue Door on Church Street, a renovated 1930s plantation home in historic Wailuku. This one-bedroom villa features a King-sized Nectar bed, memory foam sleeper sofa, spa-like bath, and a fully equipped bar area. Enjoy the on-site infrared sauna and walk to cafés, restaurants, and shops. Centrally located near ʻĪao Valley, beaches, and top Maui attractions—your perfect base for adventure and relaxation.

4.94 out of 5 average rating, 186 reviews

Flat in Kihei

Location! Tropical King Suite: Steps to Beach

@KarasMauiCondo is a unique space, your barefoot sanctuary the moment you walk through the doors, in South Shore Maui. Welcome to the redefinition of hospitality and rustic splendor. Karas Condo’s close proximity to activities, shops, beaches, dining experiences provides walk ability and convenience. Closet is packed with all the necessities to get outside, explore, and find your Aloha. 🌺 Mahalos for your interest 🤍🌺

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Other great holiday rentals in Olowalu

Superhost

Home in Maui County

4.84 out of 5 average rating, 75 reviews

Cliff House with Ocean Views in Haiku, Maui jungle

IanRating, 5 stars1 month ago

This place is gorgeous! I am so glad we chose to stay here. The views were perfect. The property was amazing. The place was very comfortable and so peaceful. I would love to come back here some day.

4.95 out of 5 average rating, 43 reviews

Kapalua Ridge #2824 - Vacation West Maui

JessRating, 5 stars3 days ago

Reached out as our previous air bnb was a nightmare once we were already on island. Joseph was quick to respond and get us in a room with less than an hours notice. The room was beautiful, ice cold ac, so many appliances in the kitchen! 100% would stay again when we come back to Maui

Flat in Wailuku

5 out of 5 average rating, 3 reviews

Wailuku Views

MarioRating, 5 stars2 weeks ago

Wow! Where do I start. I’ve travelled and stayed in AIRB&B”s all over the world. Every now and then you come across a place that truly drives the experience. This is one of those places. Beautiful, quiet, island country feel, private and safe…. I felt like I was living in a dream. Place was CLEAN 🧼 Bedding was super clean and you can tell a lot of thought went into the design. It’s upstairs, so you can walk out and hang out in the patio and witness a 360 mountain and ocean view…. It reminds me of countryside Japan so much. Vernon was super responsive and kind with check in instructions… This is the greatest deal on the island and at this price and experience, Vernon will take a lot of business from the competition. 10/10 !!!! I’m very picky, I recommend this place to EVERYONE visiting the island, you won’t regret it….

4.96 out of 5 average rating, 52 reviews

Beautiful Ground floor! Ocean and Beach Access

RobertRating, 5 stars1 month ago

Just a few seconds walk from a beautiful beach, snorkeling along the rock reef there were plenty of turtles to see. The park is a great place to watch the sunrise. You can hear the waves crashing from your bedroom. Lot's of food in walking distance, a picturesque tropical place to relax.

4.96 out of 5 average rating, 258 reviews

Soothing Waves with 180° View In Kahana, HI

CandiRating, 5 stars2 weeks ago

Sherry’s place was the perfect spot for our trip to Maui! Incredible views from the lanai, watching sea turtles swim below. It was clean and comfortable with plenty of amenities. Sherry was very responsive and gave fantastic tips to make our trip even better! We would definitely stay again!

5 out of 5 average rating, 58 reviews

Apartment in Kihei

Ma'alaea Surf Oceanfront 2 Bedroom Condo on 2nd Fr

TeresaRating, 5 stars4 weeks ago

Loved everything about the condo. The private/quiet location and the beautiful view. We walked on the beach every day. The condo is updated, nicely decorated and accommodating for 2 couples. Allison was very thoughtful and had some extra amenities in the condo like cooler, flashlights, dish soap, coffee filters, etc. Appliances worked good and the air conditioners worked great! Definitely a great place to stay!

4.97 out of 5 average rating, 30 reviews

Home in Wailuku

Maalaea Kai 307 - Maui Prime Oceanfront

HayleyRating, 5 stars6 days ago

We had the best time at this condo! It was quiet and clean and was exactly what we were hoping for! Don was incredibly responsive when I had questions or needed recommendations to rent baby gear! We had a great time and hope to Come back again