Vacation rentals in Olowalu

4.98 out of 5 average rating, 229 reviews

Guesthouse 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, 222 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✔

4.95 out of 5 average rating, 265 reviews

Lahaina Studio: Beachfront, Mountain View, Hot Tub

Pineapple Lahaina Studio invites you to experience a tranquil Maui retreat in the heart of Lahaina. Nestled within a quiet rebuilding enclave, our bright, fully‑equipped studio offers modern comforts: king bed, kitchen, AC, and our resort pool and hot tub. Step outside to abundant nature: native trees, flowers, birds, and gentle ocean breezes. A quick drive brings you to vibrant dining, shopping, and the historic Old Lahaina Luau. Ideal for travelers craving peace and access to Maui’s culture.

4.99 out of 5 average rating, 140 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, 135 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.

4.99 out of 5 average rating, 133 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.

5 out of 5 average rating, 137 reviews

Napili bay Studio Sept special$99!

Aloha🙏🙏🙏 Corner unit . 50’ vizio TV(Smart) Free WiFi King size bed Ceiling fan AC 18000 BTU Balcony’s chair and table Beach umbrella Beach chairs (2) And cooler Oven Microwave Refrigerator Pots,pans,utensils Coffee maker Complimentary coffee Set of beach towels (2) Set of towels,hand towels Etc Hair dryer Pool/all year around Iron Start up hand soap shampoo,conditioner,lotion Maui book Free parking Bbq area Toaster Blender Sal/pepper Ceiling fan 10 min walk to Napili bay

4.94 out of 5 average rating, 646 reviews

Farm stay in Haiku

Adorable Garden Gingerbread House, Makawao

Romantic hideaway! This property has the lush beauty and privacy of Hana, without the drive! Only 15-20 minutes to the airport, 10 minutes to beaches, 2 minutes to restaurants and shops...on a private gated property with organic nursery. BEAUTIFUL! Comes with a FREE FARM TOUR and/or LABYRINTH WALK with every booking! Getting married? Renewing your vows? I can perform the ceremony for you as well....free with booking! Permit Number STMP 2015 / 0001 SUP2 2013 / 0013

4.89 out of 5 average rating, 493 reviews

Guest suite in Wailuku

Oceanview & Banana Bread Near Beach-Iao-OGG-MACC

Serene, Beachy decor. Awaken to Sunrise over Haleakala & North Shore, listen to surf and local birds, and watch the ocean and harbor action- Surfers, Kiters, Sailboarders, Kanaha beach from the secluded back yard. Very Central, but you’ll want a car or Uber to get to most places- Wailuku town is 1 mile. Hosts live on-site for needed assistance, otherwise allow guests to enjoy their peace and solitude during the evenings after the day's adventures. FAST Internet

4.99 out of 5 average rating, 141 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.

4.96 out of 5 average rating, 440 reviews

Home in Wailea

Stunning ocean view, heated pool at home by Wailea

Ocean, sunset views, unique home reminiscent of a Victorian villa with heated private pool for guests in the villa, tropical gardens. Home renovated and maintained by designer. Cal King in main, second has twin beds. Pac n play and high chair are available. Open plan living with dining and relaxing on the lanai. Keawakapu beach, Wailea shops and restaurants 5 minutes drive. Your private view retreat. #BBMK 2016/0003