1. Hawaii
  2. Kihei
  3. Wailea
  4. Monthly Stay

414+ Wailea Monthly Rentals on Hawaii.Villas

Extended Stay Rental Homes By Owners Wailea

About Wailea Monthly Stay on Hawaii.Villas

HawaiiVillas monthly rentals simplify the process of finding, comparing, and booking vacation homes and condos for extended stays in Wailea. Whether you're seeking a weekly vacation rental, hotel suite, villa, cottage, or furnished apartment for extended stays, HawaiiVillas monthly holiday rentals offer a variety of options to suit your style and budget.

Wailea is renowned for its popularity with monthly stays. Our listings include rentals equipped with full kitchenettes, dryers, air conditioning, heating, indoor or private swimming pools, gyms, and hot tubs. Whether you're searching for a luxury villa, condo, pet-friendly cottage for a weekly or monthly stay in Wailea, with family, working remotely, or enjoying an extended honeymoon, HawaiiVillas offers a wide selection of monthly furnished accommodations with top amenities.

HawaiiVillas caters well to executive travelers or those relocating for work or school. We connect you with property owners offering longer-term, yet flexible rentals. Our website simplifies filtering options for guests seeking the best accommodations for groups, families, or solo travelers needing stays longer than just a few nights.

Show more
Show less

Frequently Asked Questions About Wailea Monthly Stays

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 Monthly Stays in Wailea:

To book any amount of stay in Wailea visit Hawaii.Villas rental listings, click length of stay, choose the number of days, weeks, or months you want to spend, then enter the date and destination. Some properties may need you to inquire with the property prior to booking to learn more about extended or monthly stays.
We have many pet-friendly long-term rentals in or near Wailea. The top pet-friendly rentals in Wailea are:

See all pet-friendly monthly rentals in Wailea

Yes, there are more than 414 vacation rentals in Wailea that have indoor and private swimming pools. Check out our filter option and find your best extended stay near Wailea.
Internet access is a requirement for most extended-stay travelers. Most of the holiday rentals we list have internet availability on premises.

There are 414 monthly stays available for rent in Wailea.