Apartments for Rent in Winter Park, FL Under $2,000 with Swimming Pool (82 Rentals) Page 2 of 2

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Aurora on the Trail
$1,599 - $3,372
Total Monthly Price

Total Monthly Price

Base Rent
$1,524 - $3,297
Required Monthly Fees
$75
Total Monthly Price
$1,599 - $3,372
Studio to 3 Bedroom Apartments Available Now

Aurora on the Trail

825 McCullough AveOrlando, FL 32803
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Baldwin Harbor
$1,888 - $5,817
Total Monthly Price

Total Monthly Price

Base Rent
$1,831 - $5,760
Required Monthly Fees
$57
Total Monthly Price
$1,888 - $5,817
1 to 3 Bedroom Apartments Available Now

Baldwin Harbor

1771-1887 Jake StOrlando, FL 32814
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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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Steelhouse Orlando
Rent Specials
$1,334 - $2,600
Total Monthly Price

Total Monthly Price

Base Rent
$1,222 - $2,488
Required Monthly Fees
$112
Total Monthly Price
$1,334 - $2,600
1 to 2 Bedroom Apartments Available Now

Steelhouse Orlando

750 N Orange AveOrlando, FL 32801
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Courtney At Lake Shadow
Rent Specials
$1,406 - $2,741
Total Monthly Price

Total Monthly Price

Base Rent
$1,354 - $2,689
Required Monthly Fees
$52
Total Monthly Price
$1,406 - $2,741
1 to 3 Bedroom Apartments Available Now

Courtney At Lake Shadow

545 S Keller RdOrlando, FL 32810
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The Baldwin
Rent Specials
$1,552 - $2,524
Total Monthly Price

Total Monthly Price

Base Rent
$1,452 - $2,424
Required Monthly Fees
$100
Total Monthly Price
$1,552 - $2,524
1 to 3 Bedroom Apartments Available Now

The Baldwin

800 Lombard StOrlando, FL 32807
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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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Audubon Park
$1,658 - $3,234
Total Monthly Price

Total Monthly Price

Base Rent
$1,628 - $3,204
Required Monthly Fees
$30
Total Monthly Price
$1,658 - $3,234
1 to 3 Bedroom Apartments Available Now

Audubon Park

990 Warehouse RdOrlando, FL 32803
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The Gallery at Mills Park
Rent Specials
$1,581 - $2,768
Total Monthly Price

Total Monthly Price

Base Rent
$1,527 - $2,714
Required Monthly Fees
$54
Total Monthly Price
$1,581 - $2,768
Studio to 3 Bedroom Apartments Available Now

The Gallery at Mills Park

1650 N Mills AveOrlando, FL 32803
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Sumerset Apartments
Rent Specials
$1,074 - $1,495
Total Monthly Price

Total Monthly Price

Base Rent
$1,074 - $1,495
Total Monthly Price
$1,074 - $1,495
1 to 3 Bedroom Apartments Available Now

Sumerset Apartments

1051 Lee RdOrlando, FL 32810
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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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911 N Orange Ave
Studio to 3 Bedroom Apartments

911 N Orange Ave

911 N Orange AveOrlando, FL 32801
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Gem Lake Apartments
1 to 3 Bedroom Apartments

Gem Lake Apartments

201 Monroe AveMaitland, FL 32751
  • Utilities Included
Showing Results 51-82, Page 2 of 2

Frequently Asked Questions about Winter Park Apartments with Swimming Pool

What is the Cheapest Swimming Pool apartment in Winter Park?

Currently the most affordable Apartment in Winter Park with Swimming Pool is at Kingswood Apartments listed at $900.

How much is the average rent for Winter Park Apartments with Swimming Pool?

The average rent for a Apartment in Winter Park with Swimming Pool is $2,264.

What is the largest Winter Park Apartment for rent with Swimming Pool?

Today's Apartment with Swimming Pool and the most square footage in Winter Park is a 3,513 square feet unit starting from $2,074 at Lake House.

What is the average size for Winter Park Apartments for rent with Swimming Pool?

The average size for a rental with Swimming Pool in Winter Park is currently at 660 sq ft.

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.

Helpful Local Expert Guides

decorative image for An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent article

An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent

Written by: Darla Ferrara

For many, Orlando is the place where you vacation, not live. However, this city, located in the central region of Florida, offers a vibrant tech community, plenty of outdoor activities, and some of the best schools in the country.

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Your Guide to the Perfect Orlando Neighborhood for Student Renters

Written by: Darla Ferrara

There is never a dull moment in Orlando, Florida. Along with top-tier universities, technical schools, and local colleges, there are world-class entertainment venues, the ocean within driving distance, and lots of sunshine.

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Unlock Your Orlando Commute: An Expert Guide to Ideal Neighborhoods Near Major Local Employers

Written by: Darla Ferrara

When I first moved to Orlando, Florida, in the 1990s, one of the things that drew me here was the remarkably low unemployment rates. There was a job for everyone. Two decades later, that fundamental appeal remains.

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The Soul of the City Beautiful: What Life in Orlando Is Really Like

Written by: Darla Ferrara

When people think of Orlando, Florida, they dream of theme parks and sunny weather, and rightfully so. It’s that energy that keeps this city a mainstay in the global tourist industry.

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.

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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.

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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.