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Holiday rentals near Shops at Wailea

We found 4,829 holiday rentals — enter your dates for availability

Scroll through and discover private holiday rentals close to Shops at Wailea that can be your home away from home. Whether you're travelling with your children or with friends, holiday rentals have the amenities that you need and want for your stay, which might include parking and a washer and dryer. You're sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Shops at Wailea

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Frequently asked questions

Are there any cheap holiday rentals near Shops At Wailea?
There are several affordable holiday rentals near Shops At Wailea, especially if you are flexible with location and travel dates. Budget-friendly stays are typically around AU$510 per night. Some stays offer good deals in September and October during the off-season, making it a great option for guests looking to experience the area without overspending. These rentals often include amenities such as WiFi, self-parking, and toiletries, and can range from cosy studio condos to modest family apartments, providing a clean, comfortable base for your stay.

To get the best value, consider staying slightly outside major hubs. If you're willing to drive a bit further, renting around nearby areas can be an affordable option. With a little planning, it is absolutely possible to find a comfortable stay near Shops At Wailea while keeping costs down.

*Pricing data are based on past 12 months data.
What are the top holiday rentals with pools near Shops At Wailea?
There are over 3,100 holiday rentals near Shops At Wailea that offer access to swimming pools, including both private and shared options. These properties are concentrated in the Wailea area, with many condominiums and apartments featuring outdoor pools, heated pools, and even infinity pools. Many rentals come equipped with full kitchens, Wi-Fi, sun loungers, and often multiple bedrooms, making them ideal for families or groups seeking a comfortable stay.

When selecting your rental, consider the type of pool that best suits your needs. Private pools offer seclusion and are superb for families, while shared pools often come with access to additional amenities like secured areas or children's pools. For cooler months, look for heated or indoor options to ensure year-round enjoyment. Checking availability for peak season dates is always advisable.
What are the best family holiday rentals near Shops At Wailea?
There are over 2,600 family-friendly holiday homes in the Wailea area, offering ample space and comfort for groups of all sizes. These rentals often boast multiple bedrooms and bathrooms, full kitchens, and generous living areas, all designed with families in mind. With such a wide selection, you can find stays with outdoor play areas, yards, WiFi for downtime, and washer/dryers to handle laundry during the trip.

When choosing the best fit for your family, focus on properties where adults and kids each have space to unwind, and look for homes with practical amenities like well-equipped kitchens to save on dining out. Staying nearby means less travel each day and more time enjoying the surroundings.
Are there any luxury holiday rentals near Shops At Wailea?
There are several luxury holiday rentals near Shops At Wailea that combine stunning views with modern comfort. These properties often feature amenities such as private pools, heated pools, deep soaking bathtubs, rainfall showerheads, and designer toiletries. Guests can also expect premium bedding and Egyptian cotton sheets for an enhanced stay.

These homes are ideal for families or larger groups, offering conveniences like high-end climate control and access to golf courses. Many of these top-tier stays are managed by highly rated Stayz hosts, ensuring a professional and premium experience.
How much is a holiday rental near Shops At Wailea?
Holiday rentals near Shops At Wailea offer a wide range of options to suit different budgets, making it easy for guests to enjoy a memorable stay. Budget-friendly properties typically start around AU$510 per night, providing an affordable option. Mid-range rentals, including private homes, are generally around AU$860 per night, offering more comfort and space. Upscale options can cost AU$1260 or more per night, especially for properties with premium amenities or prime locations.

Enter your destination, travel dates, and number of guests on search to see the best options. You can use filters to set a minimum and maximum nightly price range along with other preferences. Rates may vary based on the season and specific amenities, but with a little planning, guests can find a rental that perfectly balances convenience and value.

*Pricing data are based on past 12 months data.
Where should I stay when visiting Shops At Wailea?
When visiting Shops At Wailea, guests have several excellent options for holiday rentals, each offering a distinct experience. The immediate area of Wailea is a prime choice, providing direct access to the Shops At Wailea and beautiful beaches. Properties here are often just a short stroll or drive away, allowing for convenient enjoyment of the area's amenities and coastal scenery.

For those seeking a slightly different pace, the neighbouring area of Kihei offers a wide array of holiday rentals. Kihei is known for its diverse dining options and various beaches, and properties here are a short drive from Shops At Wailea, making it a great base for exploring the wider region.
What is the cheapest month to stay near Shops At Wailea?
The cheapest time to find holiday rentals near Shops At Wailea is typically during the Autumn (September to October). September is frequently the cheapest month, often providing the best deals on condos and properties, with rates often being lower compared to the peak season. Guests can often find various savings during these months, along with greater availability of holiday rentals.
Are there any top beachfront holiday rentals near Shops At Wailea
Beachfront holiday rentals near Shops At Wailea are predominantly found along the scenic shores of Wailea, offering direct access to the sand and spectacular ocean views. Properties often feature ocean-view balconies, providing a superb vantage point for the Hawaiian coastline. Many of these rentals are within walking distance to lively dining, shopping, and entertainment options, while others offer a more secluded environment for a peaceful escape along quieter stretches of beach.

Guests can expect an array of amenities such as beach chairs, umbrellas, and often oceanfront pools. Accommodation types vary from comfortable ocean-facing rooms to spacious multi-bedroom condos and apartments, many with private terraces or ample living space, ideal for families or groups.
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.