1. Hawaii
  2. Kihei
  3. Wailea
  4. Cottage Rentals

Wailea Cottage Rentals & Holiday Homes

Find the best cottages in Wailea - We found 6 exact matches

About Wailea Cottage Rentals on Hawaii.Villas

Seeking cottages to rent near Wailea? HawaiiVillas features more than 6 cottages ideal for your next trip. Discover luxury cottage rentals just miles from lakes or beaches in Wailea. These cottages boast hot baths, are family-friendly, and are conveniently located near top local attractions, ensuring guests enjoy an exceptional travel experience. HawaiiVillas offers cottages of all sizes, perfect for large groups, friends, or couples visiting Wailea.

Planning a trip to lakesides, beaches, or mountains? HawaiiVillas's cottage rentals provide a diverse selection, connecting you directly with owners to ensure the best prices.

HawaiiVillas offers 6 holiday cottages and accommodations in Wailea, featuring unique options akin to Airbnb, VRBO, and HawaiiVillas styles to suit your getaway with friends and family—whether a weekend escape, spring break, summer vacation, or annual holiday, all within your budget.

Show more
Show less

Frequently Asked Questions About Wailea Rental Cottages

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 Cottage Rentals in Wailea:

The average cost for a cottage rental in Wailea is $590 per night. Hawaii.Villas has a wide list of great cottages near Wailea that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage rentals in Wailea that allow you to bring your pet:

See all pet-friendly vacation rentals in Wailea on Hawaii.Villas

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Wailea to find one that works for you.
As of 2025, the data from Hawaii.Villas shows that there are Over 6 private swimming pools or cottages with indoor pools in the Wailea area along with other great amenities.
About 6 cottages in Wailea boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Wailea on Hawaii.Villas
Yes, there are luxury cottages in Wailea. Find more luxury, lakefront, winter, & last-minute cottage rentals near Wailea.