Photo by Chris Fiegel

Olowalu holiday rentals

We found 5,501 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Olowalu to find one that's perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll have the amenities that you expect and more, which might include a pool and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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    Enjoy full kitchens, laundry, pools, gardens and more

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Take in the beachside beauty of Olowalu

The beaches and surrounding scenery provide a peaceful ambience to your holiday home in Olowalu. This romantic city attracts visitors thanks to its shopping and restaurants. Kaanapali Beach and Whalers Village are just a couple of the must-see attractions in the area. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Olowalu

Are you looking for attractions to see during your stay? Venture out of your cosy holiday rental and experience everything that makes Olowalu a one-of-a-kind holiday spot. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Kaanapali Golf Courses (8.5 mi / 13.8 km)
  • Kaanapali Kai Course at Kaanapali Golf Resort (8.6 mi / 13.8 km)
  • Maui Nui Golf Club (12.2 mi / 19.7 km)
  • Kapalua Resort (13.2 mi / 21.2 km)
  • Kapalua Golf Club Plantation Course (13.5 mi / 21.8 km)
  • The Dunes at Maui Lani (10 mi / 16.1 km)

Exploring the natural landscape of Olowalu

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Olowalu is a great place to get outside. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Kaanapali Beach (8.7 mi / 14.1 km)
  • Napili Bay (13 mi / 20.9 km)
  • Wailea Beach (14.7 mi / 23.6 km)
  • Maui Tropical Plantation (7.9 mi / 12.7 km)
  • Black Rock (9.3 mi / 14.9 km)
  • Kahekili Beach (9.7 mi / 15.5 km)

How to get to and around Olowalu

The nearest airport is in Kapalua, HI (JHM-West Maui), located 10.9 mi (17.6 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Kahului, HI (OGG), which is 13.2 mi (21.3 km) away.

Frequently asked questions

What is the best area to stay in Olowalu when booking a holiday rental?
When considering a holiday rental in Olowalu, Hawaii, one of the most appealing areas to stay is along the coastline, where you can enjoy stunning ocean views and easy access to the beach. This picturesque region boasts a variety of properties, with options that cater to different preferences, whether you're seeking a cosy beachfront bungalow or a spacious family home.Olowalu is known for its natural beauty and tranquillity, making it an excellent choice for those looking to unwind. A popular attraction in the area is the Olowalu Cultural Reserve, which offers visitors a glimpse into the rich heritage of the Hawaiian culture, along with opportunities for hiking and exploring the local flora and fauna. Additionally, the nearby Olowalu Beach is great for swimming, snorkelling, and soaking up the sun, offering pristine sands and crystal-clear waters.Staying in this charming neighbourhood allows you to immerse yourself in the serene Hawaiian atmosphere while being just a short drive from the vibrant town of Lahaina, where you can find numerous dining and shopping options.
What are the top attractions in Olowalu?
In Olowalu, visitors can enjoy a unique blend of natural beauty and cultural experiences. One of the main attractions is the stunning Olowalu Beach, known for its crystal-clear waters and excellent snorkelling opportunities, making it a superb spot for those looking to explore marine life. The beach is framed by picturesque palm trees, providing a relaxing environment for sunbathing or picnicking.Nearby, the Olowalu Cultural Reserve offers insight into the area's rich history and traditional Hawaiian practices. This reserve is ideal for those interested in learning about the local culture and engaging in outdoor activities like hiking along scenic trails that lead to lush landscapes.Additionally, the vicinity features opportunities for whale watching during the migration season, with tours available that depart from nearby locations.
Are all fees included in the Olowalu holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Olowalu holiday homes with parking?
Stayz offers a wide selection of holiday homes in Olowalu with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Olowalu holiday homes?
You can find great discounts on holiday homes in Olowalu on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Olowalu holiday home booking on Stayz?
To find Olowalu holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Olowalu?
A long-stay holiday home in Olowalu is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Olowalu holiday home?
Book your Olowalu holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Olowalu?
Prices for holiday homes in Olowalu vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Olowalu to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.