1876+ Villas for Rent and Private Getaways in Wailea |
  1. Hawaii
  2. Kihei
  3. Wailea

Explore Wailea Vacation Rentals

About Wailea Vacation Rentals

Explore more than 1876 vacation rentals available in Wailea. These accommodations, including vacation homes and HawaiiVillas properties, boast excellent amenities and exceptional value, blending comfort and luxury. Enjoy spaciousness and convenience at a HawaiiVillas property in Wailea.

Looking for last-minute deals or the best available offers on cottages, condos, private villas, and large vacation homes? With HawaiiVillas in Wailea, you can effortlessly compare various options with a simple click. Whether you seek properties with swimming pools, hot tubs, pet-friendly policies, or expansive master suites with large screen TVs, you'll find vacation rentals by owner (RBOs) and other popular Airbnb-style accommodations near Wailea. The average room size in accommodations near Wailea is 1718.6 ft². Prices average US $849 per night.

HawaiiVillas streamlines and secures your search for vacation rentals in Wailea, often offering savings of 30-40% compared to hotel prices. Start your search today and book with confidence.

Show more
Show less

Top Rental Accommodation Types in Wailea

Type Count
Holiday Apartments 221
Vacation Homes 215
Villas 125
Cottages 6

Use these Quick Filters to Find a Vacation Rental in Wailea

★ Pro Tip: HawaiiVillas simplifies comparison of top listings across various online vacation rental platforms like Booking.com and others. Use the Advanced Filter feature to switch effortlessly between HawaiiVillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, property types, cancellation policies, prices, and more. These tools streamline the search for your ideal 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 6,198 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 1,375 Properties

Frequently Asked Questions About Wailea?

What are the top vacation rentals in Wailea?

Currently, HawaiiVillas lists over 1876 properties in the Wailea area for 2025, with more being added continuously. By consolidating listings from various websites, HawaiiVillas provides a wide selection of top properties in Wailea.

How many vacation rentals have private pools in Wailea?

Discover 72 vacation rentals featuring private pools near Wailea. Highly-rated HawaiiVillas properties with swimming pool access include:

Which vacation homes in Wailea are best for families?

If you're searching for a family-friendly vacation residence in Wailea, explore one of these highly-rated properties, all praised for their excellent reviews among families or groups visiting Wailea:

How many Hawaii.Villas vacation rentals are available in Wailea?

At present, HawaiiVillas showcases more than 1876 properties available in the Wailea area for 2025, with new listings added regularly. By aggregating listings from multiple sources, HawaiiVillas offers a diverse range of premier properties in Wailea.


People Also Ask

There are 1876 Wailea, HI Vacation Rentals

Recently Booked Vacation Rentals in Wailea