1602+ Vacation Rentals & Holiday Homes in Wailea |
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Wailea Accommodations - Hotels & Rentals

About Wailea Vacation Rentals

Discover More than 1602 Incredible Getaway Rentals Available in Wailea. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Wailea.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Wailea, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Wailea. The Average Size of Places to Stay Near Wailea is 1247.79 ft², with Prices Averaging US $888 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Wailea. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals 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: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Wailea with Online Reservations.

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 Hotels & Vacation Rentals in these Cities and Neighborhoods


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 hotels, lake houses & vacation rentals 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 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 Hotels & Vacation Rentals have private pools in Wailea?

We have 78 Hotels & Vacation 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 hotel, lake house, or vacation rental in Wailea is best for families?

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

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

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 1602 in the Wailea area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Wailea.


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