Holiday rentals near MauiWine

We found 5,092 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals near MauiWine that provide the perfect home base for your trip. Whether you're going on holiday with family or friends, holiday homes have the best amenities for hanging out with the people that matter most, including Wi-Fi and parking. No matter what you're looking for, you'll find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - MauiWine

Showing deals for:31 July - 7 Aug

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What are the best holiday rentals near Mauiwine?
The best holiday rentals near Mauiwine are typically found in the scenic Ulupalakua area, often with convenient access to the beautiful Hawaiian coastline. You will find a great selection of Condos, which are the most common type of property, as well as Private holiday houses. These holiday rentals are ideal for experiencing the local charm and enjoying the island's natural beauty. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties.

Many of these properties offer fantastic amenities so you can have a comfortable stay, such as a DeckOrPatio for enjoying the views, a HotTub for relaxation, and a Pool. These homes are ideal for couples or small families looking for a relaxing escape.
What are the top holiday rentals with pools near Mauiwine?
There are approximately 94 holiday rentals near Mauiwine that feature swimming pools, offering a range of options from private backyard pools to shared community facilities. The majority of these are condos, with some private holiday houses also available. These properties are concentrated in areas surrounding Ulupalakua, providing guests with convenient access to Mauiwine. Many of these homes are well-appointed with amenities such as full kitchens, Wi-Fi, and spacious living areas, making them suitable for families or groups seeking a comfortable stay.

When selecting a rental, consider whether a private pool for exclusive use or a shared pool with potential access to other communal facilities like hot tubs better suits your party's needs. Many pools in the region are outdoor and may be heated, making them enjoyable during cooler months. It is always wise to check for specific pool availability and heating options when making your reservation, especially if travelling during off-peak seasons.
What are the best family holiday rentals near Mauiwine?
There are over 70 family-friendly holiday rentals in the vicinity of Mauiwine, offering ample space and comfort for groups of all sizes. These properties, predominantly condos and private homes, often boast multiple bedrooms and bathrooms, full kitchens, and generous living areas designed with families in mind. Many come with outdoor play areas such as gardens or patios, and practical amenities like kitchens and even travel cribs or highchairs for younger guests.

When choosing the best fit for your family, focus on properties that offer a good separation of space for adults and children, and look for practical utilities to make your stay easier. Staying nearby means less travel time and more opportunities to enjoy Mauiwine and the surrounding area.
Are there any luxury holiday rentals near Mauiwine?
Near Mauiwine, guests can find several luxury holiday rentals that combine the stunning natural scenery with modern comfort. These properties often feature private pools, air conditioning, and breathtaking mountain views. Some of these exclusive homes also offer the indulgence of a private chef, ensuring a truly upscale dining experience during your stay.

These homes are ideal for families or larger groups, providing a comfortable and spacious environment. Many of these top-tier stays are managed by highly rated Stayz hosts, assuring a professional and premium experience.
Where should I stay when visiting Mauiwine?
When visiting Mauiwine, choosing your holiday rental location can enhance your experience of Upcountry Maui. The Kula area, situated on the slopes of Haleakalā, offers properties with stunning panoramic views of the island and the ocean. These rentals provide a peaceful retreat, with easy access to farms and gardens, and are a pleasant drive from Mauiwine.

Further down the slopes, the Makawao area provides a charming upcountry experience. This historic cowboy town offers unique shops and eateries, with holiday rentals that allow guests to enjoy a blend of local culture and natural beauty. Properties in Makawao are a convenient drive from Mauiwine, making it an excellent base for exploring.

For those seeking proximity to both the upcountry charm and the coastline, the Paia area on the North Shore is an option. While a slightly longer drive to Mauiwine, properties here offer access to beautiful beaches and a lively town centre.
What is the cheapest month to stay near Mauiwine?
The cheapest time to find holiday rentals near Mauiwine is typically during the late Autumn (November) and early Spring (April to early May), excluding any major local holidays or festivals. November frequently offers the best deals on homes and properties, with rates often lower than the peak seasons. Guests can often find various savings during these months, along with greater availability of holiday rentals.
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.
What can I expect from Stayz customer service and Stayz™ 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.
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.
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.