
Apartments for Rent in Winter Park, FL with Swimming Pool (150 Rentals) Page 2 of 3


Lake Virginia Condominiums

Chateaux du Lac

Winter Park Gardens

Mead Garden Condominiums

Park West Condominiums

Onyx Winter Park

Total Monthly Price
The Yard at Ivanhoe

The Majestic at Downtown Baldwin Park

NORA Apartments
Orlando's Best Affordable Neighborhoods
Learn about Orlando and the best places to live with original content written by our Local Expert Darla Ferrara

Total Monthly Price
Inscribe Apartments

Total Monthly Price
Gables Baldwin Park

Azul Baldwin Park

Bell Trelago

Total Monthly Price
Advenir at Magnolia

The Shores at Lake Howell

The Adeline

Total Monthly Price
The Village at Lake Lily

Newport Colony Apartments in Casselberry

Total Monthly Price
Cortland Lake Howell
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.

Citron at The Packing District

The Cannery at The Packing District

The Princeton at College Park

Total Monthly Price
Baldwin Harbor

MAA Baldwin Park

Total Monthly Price
Enders Place at Baldwin Park

Total Monthly Price
The Ivy Residences at Health Village Apartment Homes

Grand Reserve at Maitland Park

Shoreview at Baldwin Park

Evergreen Mills 50
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.

Lake Weston Point Apartments

Perla Gem Lake

Maitland City Centre

The Parker at Maitland Station Apartments

Steelhouse Orlando

Infinity off Baldwin Park

Village at Baldwin Park

Total Monthly Price
Courtney At Lake Shadow

Luna at Lake Shadow

Total Monthly Price
400 North
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.

Regency Oaks Apartments

The Baldwin

Total Monthly Price
Vida at Health Village

Total Monthly Price
Aurora on the Trail

Lake House

Adele Place

Avenues of Baldwin Park

District On Baldwin Park

The Ivy at Gatehouse

Ekos at Lake Shadow
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.
Winter Park, FL Local Guide

How much does it cost to rent an apartment in Winter Park?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winter Park Studio Apartments with Swimming Pool | $1,616 | $900 | $2,847 |
| Winter Park 1 Bedroom Apartments with Swimming Pool | $1,808 | $250 | $4,198 |
| Winter Park 2 Bedroom Apartments with Swimming Pool | $2,265 | $645 | $5,957 |
| Winter Park 3 Bedroom Apartments with Swimming Pool | $2,833 | $750 | $7,284 |
| Winter Park 4 Bedroom Apartments with Swimming Pool | $1,946 | $1,844 | $2,461 |
Browse Top Apartments in Winter Park
See all Apartments in Winter ParkExplore Winter Park
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 Ekos at Lake Shadow listed at $529.
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 $2,418.
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 $1,899 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 665 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

Where Orlando Locals Actually Live: A Renter's Guide to the Surrounding Cities
Written by: Darla Ferrara
When people think of Orlando, FL, the iconic theme parks and buzz of downtown tend to steal the spotlight.

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.

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.

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.
Articles, How-To's, and Tips

First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

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.

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.

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.