Vacation rentals in Olowalu

4.8 out of 5 average rating, 429 reviews

Condo in Wailuku

Romantic Beachfront Getaway

Your beachfront escape awaits... This is the perfect spot for your romantic getaway! Right on the beach, you'll enjoy days in the sun, romantic meals dining on the private garden lanai with views of the azure Pacific and nights falling asleep in the luxurious canopy bed listening to the ocean waves lapping at the shore. Just 30 steps to the white sand beach and warm Pacific from both the private garden lania and front door! This truly is a magical spot. Newly remodeled and updated with all the amenities (everything is brand new). You'll enjoy luxury accommodations at a fraction of what you would pay elsewhere. Maalaea Bay is perfectly located and central to the entire island so it's easy to get out and explore... Watch the sunrise from high atop the clouds at the 10,000 ft. summit of Haleakala Volcano (about 45 minutes to the summit). Shop the luxury stores of Wailea (about 20 minutes away). If it is snorkeling, fishing or whale watching that interests you, just walk 5 minutes to Maalaea Harbor and jump on one the many different boat tours leaving throughout the day. Craving a little nightlife? Lahaina is only about a 20 minute drive away. I hope you can come and stay to enjoy what I believe to be one of the best spots in Maui. See you soon !

4.97 out of 5 average rating, 214 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✔

4.92 out of 5 average rating, 118 reviews

Condo 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, 113 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, 125 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, 1,079 reviews

Apartment 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)

4.98 out of 5 average rating, 174 reviews

Sunsets and Turtles and Whales, Oh My!

Spectacular ocean views Whales and turtles galore(whale season Nov-March) Great snorkeling Gorgeous landscaping Pool, grills, shuffleboard, laundry, and huge sundeck Pristine beaches, grocery stores and world class shopping nearby Sleek and modern Maui hale Chef's kitchen Stainless steel appliances Tv & wifi Cali King bed with luxury linens Beach toys Cooling trade winds Boutique building Elevator and luggage carts Free parking Our elevator will be out of service March 31-June 14.

4.85 out of 5 average rating, 224 reviews

Condo in Kihei

WALK to beach & shops! Updated w/ AC

Yup, the blue dot is where we're at! In downtown Kihei AND across the street from the sand, the world famous Kihei beaches are literally at your backyard! Everything is literally within walking distance! 1 min walking distance to beach, supermarkets, restaurants, bars, post office and also night market (last Friday night every month). Entire place with free parking! 30 min to Lahaina, 15 min to Wailea, and 15 min to Kahului where the airport, Costco, Target and Walmart are at.

4.9 out of 5 average rating, 310 reviews

TOP FLOOR!!!! Oceanfront, free Wi-Fi, free parking

Honokowai area. Fresh & clean island vibe on the top floor, one unit away from the end. Practically hanging over the water's edge. Beautiful views of Molokai out the screened front door, as well as Lanai off the lanai. Striking floor-ceiling mirrors capture ocean views from virtually anywhere inside. Location in building catches wonderful trade winds. Listen to the sounds of the waves, just steps away & enjoy the endless sea turtle traffic right under your nose.

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.

4.98 out of 5 average rating, 180 reviews

DIRECT OCEAN FRONT STUDIO W OCEAN IS UR BACK YARD!

This is a hotel-zoned condo. It will not be affected by potential upcoming county regulations. Book with confidence!! Thank you for considering my direct ocean front studio condo in Kahana, my condo is located minutes outside of Lahaina , Kaanapali , Napili and Kapalua. You'll find the ocean view from my lanai/ room to be breathtaking and serene. This is truly an hidden gem on Maui.

Superhost

4.86 out of 5 average rating, 116 reviews

Stunning Oceanfront, Sunset and Marine Life Views

There's no denying it. The ocean brings us both joy and tranquility that truly soothes the soul. Walker's Paradise Maui welcome's you to come enjoy the breathtaking views, fall asleep and wake up to the sounds of the ocean, watch the most majestic sunsets from the lanai and feel the sea breeze in our beautifully appointed studio condo located at The Valley Isle Resort.

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Other great vacation rentals in Olowalu

5 out of 5 average rating, 7 reviews

Condo in Wailea

Tropical Escape to Wailea with Stunning Oceanview

RuslanRating, 5 stars2 weeks ago

The room was excellent and clean. Easy to parking lot on guests only. A such beautiful view the ocean from balcony and room. The bedroom is clean and soft. :)

4.98 out of 5 average rating, 53 reviews

Townhouse in Lahaina

Highly Sought After! Puamana 24-3 Ocean Retreat

ShelleyRating, 5 stars1 month ago

Thoroughly enjoyed our stay and Caitlin was very accommodating! Great place that had everything we would need!

4.98 out of 5 average rating, 93 reviews

Condo in Wailuku

Dolphin Penthouse at Milowai

AshishRating, 5 stars1 month ago

We had a wonderful time staying here. The location is perfect if you plan on exploring the island. It's centrally located with easy access to the main road to other parts of the island. The location is beautiful with great views of the ocean and harbor. It is windier in that harbor so hold on to your hats. The unit was easy to access, thanks to a dedicated elevator, clean, had lots of towels, and full of useful beach items (i.e. coolers, chairs, ice packs in the freezer, etc.) Our family would definitely stay here again!

4.98 out of 5 average rating, 47 reviews

Oceanfront Penthouse Maui Kaanapali, Aloha Getaway

ChanceRating, 5 stars3 weeks ago

This was definitely a 5 star stay. I’ve stayed at plenty of nice Airbnbs and I think this was my favorite. It’s very easy, in a good location, very safe and extremely clean. Usually you can expect some sand on the ground or on the furniture at a beach stay even after it’s been cleaned, but not here. The entire place was spotless. The hosts were very responsive and kind. The beach is right out front and great for snorkeling and sea turtles. However, the best part was definitely the stunning view. The pictures online don’t do it justice. It’s beautiful. We laid in bed every day listening to the waves and watching the sunset. We woke up to the sunrise each morning. We also spent a good bit of time, especially in the morning, just watching the water. Every time we looked out the lanai we saw at least 3-4 sea turtles and one morning we even saw a sea lion swimming next to the shore. We never turned on the TV. I cannot recommend this stay enough. It’s easily worth the money.

4.96 out of 5 average rating, 259 reviews

Soothing Waves with 180° View In Kahana, HI

TupouRating, 5 stars2 days ago

Our stay was everything we wanted. Very nice place with ocean view, private, totally awesome! We enjoyed every moment of our stay. Clean and had everything we needed! Thank you for a wonderful time in a beautiful place in Maui💕🌺

5 out of 5 average rating, 47 reviews

Condo in Wailuku

Relaxing in Maui on Oceanfront View

SteveRating, 5 stars1 month ago

We really enjoyed the proximity to the ocean surf. The are lots of things to do in Maui, but we enjoyed the condo so much we mostly just hung out. Thank you Bill for making this a great visit to Maui!