Luxury Homes for Rent in Southwest Orlando Neighborhood of Kissimmee, FL (218 Rentals)

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The most luxurious Homes in the Southwest Orlando area of Kissimmee with high-end amenities, features, and finishes.

property at 1430 Brentwood Dr

$2,500

Total Monthly Price

Total Monthly Price

Base Rent
$2,500
Total Monthly Price
$2,500

3 Bedroom, 2 Bath Home for Rent

Available Now

1430 Brentwood Dr

KissimmeeFL34746
property at 1699 Three Bars Rd

$2,625

Total Monthly Price

Total Monthly Price

Base Rent
$2,625
Total Monthly Price
$2,625

4 Bedroom, 2 Bath Home for Rent

Available Now

1699 Three Bars Rd

KissimmeeFL34744
property at 888 Florida Pky

$3,500

Total Monthly Price

Total Monthly Price

Base Rent
$3,500
Total Monthly Price
$3,500

4 Bedroom, 2 Bath Home for Rent

Available May 6

888 Florida Pky

KissimmeeFL34743
property at 4624 Cumbrian Lakes Dr

$4,000

Total Monthly Price

Total Monthly Price

Base Rent
$4,000
Total Monthly Price
$4,000

6 Bedroom, 4 Bath Home for Rent

Available Now

4624 Cumbrian Lakes Dr

KissimmeeFL34746
property at 4684 Cumbrian Lakes Dr

$4,000

Total Monthly Price

Total Monthly Price

Base Rent
$4,000
Total Monthly Price
$4,000

5 Bedroom, 3 Bath Home for Rent

Available Now

4684 Cumbrian Lakes Dr

KissimmeeFL34746

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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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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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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property at 2012 Bearing Ln

$2,725

Total Monthly Price

Total Monthly Price

Base Rent
$2,725
Total Monthly Price
$2,725

3 Bedroom, 2.5 Bath Rentals

Available Now

2012 Bearing Ln

KissimmeeFL34744

Orlando's Best Affordable Neighborhoods

Learn about Orlando and the best places to live with original content written by our Local Expert Darla Ferrara

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Showing Results 1-50, Page 1 of 5

Southwest Orlando, Kissimmee, FL Local Guide

10 Hidden Costs of Renting You Should Budget for Before Signing a Lease

Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.

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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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Pet Friendly Lifestyle
Southwest Orlando, Kissimmee, FL

Ranked #2

Among cities in Florida for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

4.0
Pet Friendly

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Best Local Schools in
Southwest Orlando, Kissimmee, FL

School data provided by Great Schools

Frequently Asked Questions about Southwest Orlando

What type of rentals are currently available in Southwest Orlando?

There are currently 268 Apartments for Rent in Southwest Orlando, FL with pricing that ranges from $850 to $17,080. There are also 741 Single Family Homes for rent, Condos, and Townhome rentals currently available in Southwest Orlando ranging from $600 to $15,000.

What is the current price range for Rental Homes in Southwest Orlando?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Southwest Orlando ranges from $600 to $15,000 with an average monthly rent of $3,054.

How much are larger Three and Four Bedroom Rentals in Southwest Orlando?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Southwest Orlando range from $1,450 to $9,361, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,550 to $4,000. Four Bedroom Single-Family rentals are also available starting from $1,850 and Four Bedroom Apartments start at $1,650.

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

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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.

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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.

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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.