2085+ Luxury Vacation Rentals & Cabins in Wailea |
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Wailea Cabin Rentals

About Wailea Vacation Rentals

There are more than 2085 incredible getaway rentals that are available in Wailea. These choices include cabins, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Stay Close to Nature with Cabinns.com and uncover great stays in Wailea.

Cabinns.com features numerous last-minute deals on private villas, hotels, and cabin rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Cabinns.com in Wailea, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the Cabinns.com vacation rentals, resorts, and Airbnb-style properties in Wailea. Places to stay near Wailea are 1704.97 ft² on average, with prices averaging $845 a night.

Cabinns.com helps you find the ideal holiday rental to create a lifetime of travel memories in Wailea. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect cabin retreat today.

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Top Cabin Rentals, Cottages, and Holiday Home Rentals in Wailea

Type Count
Holiday Apartments 273
Vacation Homes 246
Villas 129
Cottages 6

Use these Quick Filters to Find a Vacation Rental in Wailea

★ Pro Tip: Cabinns.com is a cabin vacation rental website, pulling some of the top cabins, luxury resorts, and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible cabin resorts and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Wailea with Cabinns.com.

Weather in Wailea, HI

View the weather forecast for Wailea before booking your Wailea Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Find Nearby Cabin Rentals in these Cities & Neighborhoods


South Maui 6,191 Properties
Keawakapu Beach 5,468 Properties
Mokapu Beach 5,461 Properties
Ulua Beach 5,457 Properties
Ulua Beach Park 5,452 Properties
Wailea Shopping Village Shopping Center 5,451 Properties
Shops at Wailea 5,439 Properties
Wailea Beach 5,293 Properties
Polo Beach 4,632 Properties
Wailea Blue Golf Course 4,422 Properties
Palauea Beach 3,644 Properties
Makena 1,298 Properties

Complexes around Wailea, HI


Sugar Beach Resort Kihei 173 Properties
Grand Champions 33 Properties
Makena Surf 29 Properties
Polo Beach Club 7 Properties
Residence Inn 3 Properties
Ocean Villa 2 Properties

Frequently Asked Questions About Wailea?

What are the top cabins, lake houses & summer homes in Wailea?

We provide an array of great vacation destinations in Wailea. If you are looking to stay in or around the Wailea area, make sure to browse our options to find a premium cabin resort or rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Wailea:

How many cabin rentals and resorts have private pools in Wailea?

We have 81 cabins, luxury resorts, and holiday home rentals featuring a private pool in and near Wailea. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which cabin rental, resort, or holiday home in Wailea is best for families?

Searching for a family-friendly cabin in Wailea? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfectly fit families of all sizes.

How many hotels, resorts, or cabin rentals are available in Wailea?

Cabinns.com offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Cabinns.com in 2025 is over 2085 in the Wailea area, and that number rises every day. By combining listings from multiple websites and travel providers, Cabinns.com can provide you with a diverse amount of choices of the best luxury stays in Wailea.


People Also Ask

There are 26 hotels in Wailea 29 resorts, and 648 rentals

Recently Booked Private Villas, Cabin Resorts, and Rentals Wailea