Luxury Homes for Rent in the 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 2112 Bunker View Ct

$2,500

Total Monthly Price

Total Monthly Price

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

3 Bedroom, 3 Bath Home for Rent

Available Aug 2

2112 Bunker View Ct

KissimmeeFL34746
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 1677 Three Bars Rd

$2,800

Total Monthly Price

Total Monthly Price

Base Rent
$2,800
Total Monthly Price
$2,800

4 Bedroom, 2 Bath Home for Rent

Available Now

1677 Three Bars Rd

KissimmeeFL34744
property at 30 Adams Ave

$3,250

Total Monthly Price

Total Monthly Price

Base Rent
$3,250
Total Monthly Price
$3,250

6 Bedroom, 2 Bath Home for Rent

Available Now

30 Adams Ave

KissimmeeFL34744
property at 4005 Venetian Bay Dr

$3,884

Total Monthly Price

Total Monthly Price

Base Rent
$3,884
Total Monthly Price
$3,884

4 Bedroom, 3.5 Bath Home for Rent

Available Dec 31, 2027

4005 Venetian Bay Dr

KissimmeeFL34741
property at 4345 Quote St

$6,506

Total Monthly Price

Total Monthly Price

Base Rent
$6,506
Total Monthly Price
$6,506

4 Bedroom, 3 Bath Home for Rent

Available Aug 15

4345 Quote St

KissimmeeFL34746

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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property at 2600 Avondale Ct

$3,944

Total Monthly Price

Total Monthly Price

Base Rent
$3,944
Total Monthly Price
$3,944

3 Bedroom, 2.5 Bath Home for Rent

Available Oct 31

2600 Avondale Ct

KissimmeeFL34746
property at 1775 Manarola St

$2,519

Total Monthly Price

Total Monthly Price

Base Rent
$2,519
Total Monthly Price
$2,519

1 Bedroom, 1 Bath Home for Rent

Available Jul 20

1775 Manarola St

KissimmeeFL34741
property at 2641 Scrapbook St

$3,541

Total Monthly Price

Total Monthly Price

Base Rent
$3,541
Total Monthly Price
$3,541

4 Bedroom, 3 Bath Home for Rent

Available Aug 13

2641 Scrapbook St

KissimmeeFL34746
property at 4721 Clock Tower Dr

$2,802

Total Monthly Price

Total Monthly Price

Base Rent
$2,802
Total Monthly Price
$2,802

2 Bedroom, 2 Bath Home for Rent

Available Aug 2

4721 Clock Tower Dr

KissimmeeFL34746

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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property at 4976 Windermere Ave

$2,765

Total Monthly Price

Total Monthly Price

Base Rent
$2,765
Total Monthly Price
$2,765

4 Bedroom, 3 Bath Home for Rent

Available Aug 16

4976 Windermere Ave

KissimmeeFL34746
property at 4486 Monado Dr

$7,230

Total Monthly Price

Total Monthly Price

Base Rent
$7,230
Total Monthly Price
$7,230

8 Bedroom, 5 Bath Home for Rent

Available Jan 31, 2028

4486 Monado Dr

KissimmeeFL34746
property at 210 Ballo Dr

$4,486

Total Monthly Price

Total Monthly Price

Base Rent
$4,486
Total Monthly Price
$4,486

6 Bedroom, 3 Bath Home for Rent

Available Aug 8

210 Ballo Dr

KissimmeeFL34746

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

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property at 2463 Ixora Ct

$2,500

Total Monthly Price

Total Monthly Price

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

3 Bedroom, 2 Bath Rentals

Available Now

2463 Ixora Ct

KissimmeeFL34744

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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Showing Results 1-50, Page 1 of 5

Southwest Orlando, Kissimmee, FL Local Guide

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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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 281 Apartments for Rent in Southwest Orlando, FL with pricing that ranges from $325 to $17,493. There are also 731 Single Family Homes for rent, Condos, and Townhome rentals currently available in Southwest Orlando ranging from $600 to $14,000.

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 $14,000 with an average monthly rent of $2,632.

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 $1,064 to $8,451, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,200 to $4,490. Four Bedroom Single-Family rentals are also available starting from $1,850 and Four Bedroom Apartments start at $1,668.

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 Renters Insurance 101: What It Is, What It Covers, and Why You Need It article

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

Written by: Robin Stewart

Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

decorative image for Apartment Occupancy Rates: Renter Attraction vs Renter Retention article

Apartment Occupancy Rates: Renter Attraction vs Renter Retention

Written by: Robin Stewart

There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

decorative image for How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide article

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Written by: Robin Stewart

Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

decorative image for Pet-Friendly Renting: Everything You Need to Know Before You Move article

Pet-Friendly Renting: Everything You Need to Know Before You Move

Written by: Christine Leonard, Esq.

For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.