Luxury Homes for Rent in Wailea, HI (59 Rentals)

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The most luxurious Homes in Wailea with high-end amenities, features, and finishes.

property at 480 Kenolio Rd

$2,600 - $2,895

2 Bedroom Rentals

Available Now

480 Kenolio Rd

KiheiHI96753

The Art of the Rental Viewing: What to look for during a property tour

Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

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property at 3676 Lower Honoapiilani Rd

$3,450

Total Monthly Price

Total Monthly Price

Base Rent
$3,450
Total Monthly Price
$3,450

2 Bedroom, 1 Bath Condo for Rent

Available Now

3676 Lower Honoapiilani Rd, Unit F102

3676 Lower Honoapiilani Rd
LahainaHI96761

Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

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property at 8 Polohina Ln

$3,850

Total Monthly Price

Total Monthly Price

Base Rent
$3,850
Total Monthly Price
$3,850

3 Bedroom, 2 Bath Condo for Rent

Available Now

8 Polohina Ln, Unit 1

8 Polohina Ln
LahainaHI96761
property at 3950 Kalai Waa St

$4,050

Total Monthly Price

Total Monthly Price

Base Rent
$4,050
Total Monthly Price
$4,050

2 Bedroom, 2 Bath Condo for Rent

Available Now

3950 Kalai Waa St, Unit M202

3950 Kalai Waa St
KiheiHI96753
property at 2141 Awihi Pl

$4,200

Total Monthly Price

Total Monthly Price

Base Rent
$4,200
Total Monthly Price
$4,200

2 Bedroom, 2 Bath Townhome for Rent

Available May 1

2141 Awihi Pl

KiheiHI96753
property at 3150 Wailea Alanui Dr

$4,500

Total Monthly Price

Total Monthly Price

Base Rent
$4,500
Total Monthly Price
$4,500

1 Bedroom, 2 Bath Condo for Rent

Available Now

3150 Wailea Alanui Dr, Unit 3807

3150 Wailea Alanui Dr
KiheiHI96753

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.

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Showing Results 1-50, Page 1 of 2

Wailea, HI Local Guide

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.

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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.

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Cash 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.

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Quick Rent Budget Calculator

How much rent can you afford?

The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.

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Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Wailea, HI Rentals by Map

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See the most popular apartments and homes in Wailea, HI

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Frequently Asked Questions about Wailea

What type of rentals are currently available in Wailea?

There are currently 41 Apartments for Rent in Wailea, HI with pricing that ranges from $1,915 to $13,891. There are also 62 Single Family Homes for rent, Condos, and Townhome rentals currently available in Wailea ranging from $1,995 to $10,000.

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 $1,995 to $10,000 with an average monthly rent of $4,642.

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

decorative image for Maximizing Your Refund: Essential Tax Tips for Renters article

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.

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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.

decorative image for A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment article

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.

decorative image for Renting with Roommates: Realistic Expectations for Shared Lease article

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.