Holiday rentals near Wailea Beach

We found 4,847 holiday rentals — enter your dates for availability

Scroll through and discover holiday rentals within easy reach of Wailea Beach that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the amenities that you need and want for your stay, which might include parking and a washer and dryer. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

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Frequently asked questions

What are the best holiday rentals near Wailea Beach?
The best holiday rentals near Wailea Beach are predominantly located in the Wailea district of Kihei, Hawaii. You will find a wide array of properties, primarily consisting of elegant condos with ocean views and spacious apartments, many within walking distance of the beach. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties. You can easily find the best holiday rentals near Wailea Beach right in this desirable area.

Many of these rentals offer desirable amenities such as shared pools for a refreshing dip, private balconies for enjoying the tropical air, and laundry facilities for your convenience. These homes are ideal for couples or small families seeking a relaxing beach holiday.
Are there any cheap holiday rentals near Wailea Beach?
There are several affordable holiday rentals near Wailea Beach, especially if you are flexible with location and travel dates. Budget-friendly stays are typically around AU$510 per night. You might find great deals in September and October, making it a good option for guests looking to experience the area without overspending. These rentals often include free amenities such as WiFi, toiletries, and self-parking, so you can have a comfortable stay.

To get the best value, consider staying slightly outside the immediate Wailea area. 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 Wailea Beach while keeping costs down.

*Pricing data are based on past 12 months data.
What are the best pet-friendly holiday rentals near Wailea Beach?
There are dozens of pet-friendly holiday rentals near Wailea Beach, with 49 properties welcoming pets. These rentals, primarily condos and apartments in Kihei, offer essential comforts like fully equipped kitchens and Wi-Fi, along with features beneficial for pets such as easy outdoor access. Guests can find properties that accommodate dogs and cats, as well as service animals, ensuring a comfortable stay for all members of the family.

When searching for the best pet-friendly holiday rentals near Wailea Beach, remember to review individual house rules regarding pet size restrictions and any additional fees. Wailea Beach is generally welcoming to pets, particularly in less crowded sections, providing ample space to roam.
What are the top holiday rentals with pools near Wailea Beach?
There are over 3,100 holiday rentals near Wailea Beach that feature swimming pools. Guests can choose from a wide variety, including properties with private backyard pools, shared community pools, and even some with indoor options. These properties are concentrated in the Wailea area and often include amenities such as full kitchens, Wi-Fi, and comfortable living spaces, making them ideal for families and groups seeking a relaxing stay.

When selecting your ideal rental, consider the benefits of different pool types. Private pools offer personal enjoyment and are superb for families desiring seclusion, while shared pools often come with access to additional facilities like fitness centres or hot tubs. Many properties offer heated pools, ensuring comfort during cooler periods. Checking availability in advance, especially for peak seasons, will help secure your preferred property.
What are the best family holiday rentals near Wailea Beach?
There are over 2,500 family-friendly holiday homes in the Wailea area near Wailea Beach, offering a wide array of options for groups. These properties, predominantly condos and apartments, provide ample space with multiple bedrooms and bathrooms, ensuring comfort for all guests. Critical family amenities often include full kitchens for preparing meals, outdoor play areas like patios, gardens, or secured yards, and practical features such as washer/dryers. Many also offer entertainment like HDTVs, video game consoles, and a selection of books and games for children.

When selecting a holiday rental for your family, look for homes that offer distinct sleeping areas for adults and children, and consider properties with conveniences like cribs, highchairs, and stair gates to make your stay smoother. Staying close to Wailea Beach means spending less time travelling and more time enjoying the beautiful surroundings.
Are there any luxury holiday rentals near Wailea Beach?
Around Wailea Beach, there are several luxury holiday rentals that combine stunning scenery with modern comfort. Guests can find properties featuring amenities such as private pools, deep soaking bathtubs, rainfall showerheads, and premium bedding. Many also offer spectacular sea views, designer toiletries, and options for a private chef, ensuring an exceptional stay.

These homes are ideal for families or larger groups, providing conveniences like climate control and spacious suites. 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 Wailea Beach?
Holiday rentals near Wailea Beach 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 privacy. Upscale options can cost AU$1260 or more per night, especially for properties with additional space, 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 Wailea Beach?
When visiting Wailea Beach, the Wailea area itself offers a prime location with many holiday rental properties. Staying in Wailea provides direct access to the beach and nearby championship golf courses, high-end shopping, and fine dining.

For those seeking a slightly more secluded feel with excellent ocean views, properties in the Makena area are a wonderful choice. This area is a short drive from Wailea Beach and offers larger properties with significant privacy, superb for a tranquil escape.

Alternatively, staying in the nearby Kihei area provides a wider range of holiday rental options and is just a short drive from Wailea Beach. Kihei offers a more local atmosphere with diverse dining and shopping experiences, while still providing convenient access to the beautiful beaches of Wailea.
What is the cheapest month to stay near Wailea Beach?
The cheapest time to find holiday rentals near Wailea Beach is typically during the late Autumn (September to October), excluding any major local festivals. September is frequently the cheapest month, often providing better deals on condos and homes, with rates often 20% lower compared to peak season. Guests can often find various savings and greater availability for properties during these months.
Are there any top beachfront holiday rentals near Wailea Beach
Beachfront holiday rentals near Wailea Beach are predominantly found along Wailea Alanui Drive, offering direct access to the sand and breathtaking ocean views. Many properties feature ocean-view balconies or terraces, placing guests just steps from the water. While Wailea Beach itself provides a more tranquil setting, nearby areas offer walkability to lively dining and shopping options, balancing relaxation with convenience.

Guests can expect amenities such as beach chairs, umbrellas, and oceanfront pools, with some properties also offering onsite dining. Accommodation types range from ocean-facing rooms and suites to multi-bedroom units with private terraces, suiting individual guests or larger 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.

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