Apartments for Rent in Winter Park, FL Under $1,500 with Swimming Pool (47 Rentals)

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Apartment Common Area Rules: What Renters Need to Know

From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.

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Atlas at Winter Park
$1,421 - $2,004
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Total Monthly Price

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$1,421 - $2,004
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1 to 3 Bedroom Apartments Available Now

Atlas at Winter Park

3733 N Goldenrod RdWinter Park, FL 32792
Family Friendly
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Solis at Winter Park
Rent Specials
$1,352 - $1,539
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$1,352 - $1,539
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1 to 2 Bedroom Apartments Available Now

Solis at Winter Park

7502 Sun Key BlvdWinter Park, FL 32792
Student Housing
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Understanding Amenity Fees: Know Where You Might Be Able to Save Money

What are amenity fees and are they optional? This guide breaks down everything you need to know about apartment amenity fees, including when you can opt out and how you might be able to lower your rent.

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property at 2500 Lee Rd

$1,465

Total Monthly Price

Total Monthly Price

Base Rent
$1,465
Total Monthly Price
$1,465

1 Bedroom, 1 Bath Condo for Rent

Available Now

2500 Lee Rd, Unit 244

2500 Lee Rd
Winter ParkFL32789
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Advenir at Magnolia
Rent Specials
$1,147 - $1,667
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$1,147 - $1,667
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Studio to 2 Bedroom Apartments Available Now

Advenir at Magnolia

210 Welcome WayFern Park, FL 32730
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It's time to soak up some sun!

One of the easiest and more obvious ways of enjoying the summer sun is to lounge out by your community pool. Learn a Few Rules to Keep in Mind while at the pool.

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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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Sumerset Apartments
$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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property at 2426 Branch Way

$1,200

Total Monthly Price

Total Monthly Price

Base Rent
$1,200
Total Monthly Price
$1,200

1 Bedroom, 1 Bath Condo for Rent

Available Now

2426 Branch Way, Unit 200

2426 Branch Way
MaitlandFL32751

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

Orlando is much more than theme parks. Uncover the city's rich history, diverse neighborhoods like Winter Park and Downtown, and its bustling cultural and culinary life.

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property at 860 N Orange Ave

$1,375 - $2,200

Studio To 2 Bedroom Rentals

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860 N Orange Ave

OrlandoFL32801
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Gem Lake Apartments
1 to 3 Bedroom Apartments

Gem Lake Apartments

201 Monroe AveMaitland, FL 32751
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Showing Results 1-47, Page 1 of 1

Winter Park, FL Local Guide

Your Guide to the Perfect Orlando Neighborhood for Student Renters

Learn About the Best Neighborhoods to Rent Near College Campuses in Orlando, FL | Find Orlando Off-Campus Student Housing at ApartmentHomeLiving.com

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

Explore Winter Park, FL Rentals by Map

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See the most popular apartments and homes in Winter Park, FL

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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 $2,303.

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 $1,954 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

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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

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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.

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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.

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Creative Ways Developers Reimagine Retail Spaces as Residential Units

Written by: Robin Stewart

Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.

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Neighborhood and Market Insights: How to Choose the Right Area to Rent

Written by: Robin Stewart

Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.