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Wailea Vacation Rentals & One Degree Stays Homes

About Wailea Vacation Rentals

There are more than 1600 vacation rentals that are available in Wailea. These rentals, including vacation rentals, One Degree Stays Homes (ODSs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an ODS property in Wailea.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With OneDegreeStays Wailea, you have the flexibility of comparing different options of various deals with a single click. Looking for an ODS with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (ODSs), and other popular Airbnb-style properties in Wailea. Places to stay near Wailea are 1248.29 ft² on average, with prices averaging US $884 a night.

OneDegreeStays makes it easy and safe to find and compare vacation rentals in Wailea with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

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Top Rental Accommodation Types in Wailea

Type Count
Holiday Apartments 207
Vacation Homes 186
Villas 109
Cottages 6

Use these Quick Filters to Find a Vacation Rental in Wailea

★ Pro Tip: OneDegreeStays makes it easy to compare the best listings on ODS homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between ODS homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Wailea.

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

Other Places to Stay in Wailea, HI


South Maui 6,140 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 1,388 Properties

Frequently Asked Questions About Wailea?

What are the top vacation rentals in Wailea?

There are a lot of options in Wailea. If you plan on staying in the Wailea area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Wailea:

How many vacation rentals have private pools in Wailea?

There are 84 vacation rentals with private pools near Wailea. Top-rated ODS homes that have access to a swimming pool include:

Which vacation homes in Wailea are best for families?

If you are looking for a family-friendly vacation home in Wailea, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Wailea:

How many onedegreestays vacation rentals are available in Wailea?

Currently, the total number of properties listed by One Degree Stays in 2025 is over 1600 in the Wailea area, and still counting. By aggregating listings from multiple websites, One Degree Stays offers an immense amount of choice of the best ODS properties in Wailea. 


People Also Ask

There are 1600 Wailea, HI Vacation Rentals

Recently Booked Vacation Rentals in Wailea