1879+ Private Villas and Holiday Rentals in Wailea |
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Wailea Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Wailea

Discover more than 1879 vacation rentals available in Wailea. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Wailea.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Wailea, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Wailea. On average, places to stay near Wailea offer 1244.45 ft², with nightly prices averaging د.إ.‏3,681.

With Casai, finding and comparing holiday rentals in Wailea is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Wailea

Type Count
Holiday Apartments228
Vacation Homes202
Villas120
Cottages6

Use these Quick Filters to Find a Holiday Rental in Wailea

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the 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 5,991 Properties
Keawakapu Beach 5,545 Properties
Mokapu Beach 5,535 Properties
Ulua Beach 5,530 Properties
Ulua Beach Park 5,529 Properties
Wailea Shopping Village Shopping Center 5,525 Properties
Shops at Wailea 5,515 Properties
Wailea Beach 5,371 Properties
Polo Beach 4,689 Properties
Wailea Blue Golf Course 4,439 Properties
Palauea Beach 3,843 Properties
Makena 1,296 Properties

Frequently Asked Questions About Wailea?

What are the top holiday rentals in Wailea?

With numerous options available in Wailea, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Wailea:

How many holiday rentals have private pools in Wailea?

Discover a selection of holiday rentals with private pools near Wailea with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Wailea are best for families?

If you're searching for a family-friendly holiday home in Wailea, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Wailea:

How many Casai.ae holiday rentals are available in Wailea?

As of 2026, Casai boasts over 1879 properties listed in the Wailea area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Wailea.


People Also Ask

There are 1879 Wailea, HI Holiday Rentals

Recently Booked Holiday Rentals in Wailea