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Wailea Villa Rentals & Homes

Find villas near Wailea - We found 124 exact matches

About Wailea Villa Rentals on Sister Bay Condo Rentals

Sister Bay Condo Rentals has more than 124 villas near Wailea. These rentals have all the luxury accoutrements to give you comfort, including amenities such as - private swimming pools, WIFI, spas, hot tubs, and more.

Sister Bay Condo Rentals has a wide range of villa rentals near Wailea, and there are different options for families, friends, or even couples. These rentals come in unique styles or sizes that would definitely suit your needs.

Sister Bay Condo Rentals offers expectational rental villas that are out of the ordinary and not found elsewhere, whether you are traveling on a beachfront, seaside, mountain, or any destination. Sister Bay Condo Rentals is an all-in-one travel platform that matches you with the perfect rental villa in Wailea for your dream vacation, including top travel locations in the USA & the Rest of the World. Many have private pools, luxury bedrooms, and even features like tennis courts, beach volleyball, spas, fitness clubs & more.

Sister Bay Condo Rentals Villas are available for last-minute bookings and may include special offers for Airbnb, VRBO & Sister Bay Condo Rentals-style villas. So find your last-minute getaway today with Sister Bay Condo Rentals in Wailea, and get ready to enjoy maximum comfort on your next holiday.

Frequently Asked Questions About Wailea Villa Rentals

What are the top rated Villa 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 Villa Rentals in Wailea:

What is the rate per night for renting a villa near Wailea?

At Sisterbaycondorentals, the average rental fee for standard villas in Wailea is $1,989 per night. Sisterbaycondorentals has a large database of quality villas near Wailea that are suitable for families, a romantic getaway, or a solo trip with single or multiple bedrooms.

Are there any rental villas in Wailea that are suitable for families?

Most of our listed villas are suitable for families. The number of rooms varies, and you can check out the complete list of villas in Wailea to find what works for you.

Do your rental villas in Wailea have indoor swimming pools?

Based on the 2026 data from our Sisterbaycondorentals site, there are more than 124 private swimming pools or villas with indoor pools in or near Wailea.