
Apartments for Rent in Winter Park, FL Under $2,000 with Swimming Pool (97 Rentals) Page 2 of 2


Citron at The Packing District

The Cannery at The Packing District

The Princeton at College Park

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

Evergreen Mills 50

Lake Weston Point Apartments

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
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.

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
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.

Ekos at Lake Shadow

Total Monthly Price
Audubon Park

Total Monthly Price
The Gallery at Mills Park

Kingswood Apartments

Total Monthly Price
Sumerset Apartments

860 North Orange Avenue, Unit Studio

468 Banyon Tree Cir, Unit 202

1521 Legacy Club Dr

860 N Orange Ave, Unit 371
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.

860 N Orange Ave, Unit 268

860 N Orange Ave, Unit 860 N Orange Ave 464

110 Zora Pl, Unit 3-206

110 Zora Pl, Unit 5-312

110 Zora Pl, Unit 6-209

110 Zora Pl, Unit 5-205

2422 Branch Way, Unit 104

1000 Lake of the Woods Blvd, Unit Apartment C103

551 Flemming Way, Unit 201
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.

Uptown Place Apartments

Gem Lake Apartments
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 | $1,615 | $900 | $2,847 |
| Winter Park 1 Bedroom Apartments | $1,809 | $250 | $4,187 |
| Winter Park 2 Bedroom Apartments | $2,261 | $645 | $5,755 |
| Winter Park 3 Bedroom Apartments | $2,814 | $750 | $7,284 |
| Winter Park 4 Bedroom Apartments | $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 $2,421.
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 $1,893 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.
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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
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Unlock Your Orlando Commute: An Expert Guide to Ideal Neighborhoods Near Major Local Employers
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Your Guide to the Perfect Orlando Neighborhood for Student Renters
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First Apartment Regrets: Real Renters Share What They'd Do Differently
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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.