85 Walaka St
KiheiHI96753
Cheap Homes for Rent in Wailea, HI from $1,800 (5 Rentals)
Search the lowest-cost Homes available for rent right now in Wailea.
160 Keonekai Rd
KiheiHI96753
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.
1450 S Kihei Rd
KiheiHI96753
169 Ahekolo Pl
KiheiHI96753
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.
2135 S Kihei Rd
KiheiHI96753
Showing Results 1-5, Page 1 of 1
Wailea, HI Local Guide
Your fate is sealed (by this seal) by MarkSullivan is licensed under CC BY-SA 3.0
How much does it cost to rent a home in Wailea?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Wailea 2 Bedroom Homes for Rent | $4,978 | $2,800 | $10,000+ |
| Wailea 3 Bedroom Homes for Rent | $6,599 | $3,500 | $10,000+ |
| Wailea 4 Bedroom Homes for Rent | $8,598 | $7,800 | $10,000+ |
Browse Top Homes for Rent in Wailea
Explore Wailea
Wailea, HI Local Guide
- Nearby Cities
- ZIP codes
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Cheapest Available Wailea Apartments for Rent and Nearby
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Kaulana Mahina | O'io - Affordable 120 | 1BR,1BA | $2,684 |
| Wailele Ridge of Maui | 3x2.5 1252 | 3BR,2BA | $5,634 |
Best Value Apartments for Rent in Wailea, HI and Nearby
As of February 25, 2026 the best value apartment in the Wailea area is the $4.50 price per square foot 3x2.5 1252 Model at Wailele Ridge of Maui in the starting from $5,634. The second greatest value Wailea apartment is the 50 Puu Anoano St Model at 50 Puu Anoano St, Unit 3705 starting at $5,500 with a $4.45 price per square foot in the Paunau Ahupua`a neighborhood. Here is today’s list of the best values for Wailea apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| Wailele Ridge of Maui | 3x2.5 1252 | 3BR,2.5BA | $4.50 |
| 50 Puu Anoano St, Unit 3705 | 50 Puu Anoano St | 2BR,2BA | $4.45 |
| 50 Waiohuli St, Unit F | 50 Waiohuli St | 2BR,2BA | $3.27 |
| 91 Kopi Ln, Unit 1-104 | 91 Kopi Ln | 2BR,2BA | $3.78 |
| Kaulana Mahina | O'io - Affordable 120 | 1BR,1BA | $4.70 |
| 170 Kuli Puu St, Unit S.Kihei Cottage | 170 Kuli Puu St | 1BR,1BA | $4.64 |
Don't Settle: How to Negotiate Your Apartment Lease and Save Money
Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.
Read Article
The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
Read ArticleCash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
Read ArticleQuick Rent Budget Calculator
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Explore Wailea, HI Rentals by Map
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 49 Apartments for Rent in Wailea, HI with pricing that ranges from $1,795 to $21,937. There are also 50 Single Family Homes for rent, Condos, and Townhome rentals currently available in Wailea ranging from $1,800 to $11,000.
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 $1,800 to $11,000 with an average monthly rent of $5,670.
How much are larger Three and Four Bedroom Rentals in Wailea?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Wailea range from $3,200 to $5,899, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,500 to $11,000. Four Bedroom Single-Family rentals are also available starting from $7,800 and Four Bedroom Apartments start at $3,900.
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
Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.
18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.
A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.
Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.