Holiday rentals near The Skyline Trail

We found 3,354 holiday rentals — enter your dates for availability

Choose the right holiday rental that's near The Skyline Trail. Holiday homes provide the amenities that you need and want for your family, friends or furry companion, such as Wi-Fi and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - The Skyline Trail

Showing deals for:19 June - 26 June

Image gallery for Oceanview 5th Floor Retreat Steps from the Beach,

Ocean view
9.2 out of 10, Wonderful, (90 reviews)
Wonderful
(90 reviews)

Oceanview 5th Floor Retreat Steps from the Beach,

Kihei

6% off
Price is AU$2,180
for 7 nights, 1 apartment
AU$311 per night
includes taxes & fees
Oceanview 5th Floor Retreat Steps from the Beach,

Find spaces that suit your style

  • 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

Where should I stay when visiting The Skyline Trail?
When visiting The Skyline Trail, guests have excellent options in the Upcountry Maui area. Kula, situated on the slopes of Haleakala, offers properties with stunning views and a tranquil setting. This area is a short drive from The Skyline Trail, providing convenient access to the trail and other local attractions.

Another excellent choice is Makawao, a charming cowboy town known for its unique shops and local art galleries. Rentals here provide a different character, with a strong sense of local culture and easy access to the scenic drives leading to The Skyline Trail.

For those seeking a slightly more secluded experience, the Olinda area offers holiday rentals amidst lush greenery, providing a peaceful retreat after a day of exploring. These properties are well-positioned for accessing The Skyline Trail by car.
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.