
2 Bedroom Homes for Rent in Wailea, HI (20 Rentals)


Total Monthly Price
155 Wailea Ike Pl, Unit SI ID1436437P

Total Monthly Price
2575 S Kihei Rd, Unit SI ID1436434P

Total Monthly Price
2575 S Kihei Rd, Unit SI ID1436436P

Total Monthly Price
1299 Uluniu Rd, Unit SI ID1035894P

2709 Kauhale St
Renting with Roommates: Realistic Expectations for Shared Lease
Sharing a lease? Learn how to set clear expectations with your roommates on routines, bills, and cleaning to ensure a successful and peaceful shared living arrangement.

3258 Waileia Pl

160 Keonekai Rd

2747 S Kihei Rd

2531 S Kihei Rd

44 Kanani Rd

3950 Kalai Waa St
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

32 Hune One Ln

3150 Wailea Alanui Dr

18 Upena Ln

40 Kai Malu Dr

71 Wailea Gateway Pl

36 Kai Malu Dr
Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

3676 Lower Honoapiilani Rd, Unit A303

3676 Lower Honoapiilani Rd, Unit F102
Wailea, HI Local Guide

How much does it cost to rent a home in Wailea?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
Wailea 2 Bedroom Homes for Rent | $4,324 | $2,650 | $8,000 |
| Wailea 3 Bedroom Homes for Rent | $6,189 | $3,000 | $10,000+ |
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Wailea, HI Local Guide
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Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University
From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.
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See the most popular apartments and homes in Wailea, HI
Frequently Asked Questions about Wailea
What type of rentals are currently available in Wailea?
There are currently 42 Apartments for Rent in Wailea, HI with pricing that ranges from $1,875 to $22,392. There are also 62 Single Family Homes for rent, Condos, and Townhome rentals currently available in Wailea ranging from $1,900 to $11,500.
What is the current price range for Rental Homes in Wailea?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Wailea ranges from $1,900 to $11,500 with an average monthly rent of $3,755.
Expert Rental Resources
The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.
Articles, How-To's, and Tips

Neighborhood and Market Insights: How to Choose the Right Area to Rent
Written by: Robin Stewart
Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Written by: Lauren Harrington
I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.

Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
Written by: Lauren Harrington
This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.