
Pet Friendly Homes for Rent in Winter Park, FL (172 Rentals)
Homes for rent in Winter Park that love your dogs or cats as much as you do!


2924 Antique Oaks Cir, Unit 48

2399 Antilles Dr

2383 Sun Valley Cir, Unit Winter Park

3217 Royal St

Total Monthly Price
662 Callahan St, Unit SI ID1545989P

7423 Antietam Ct E

5206 Tangerine Ave

333 Cornwall Rd

2772 Prism Pt
Where Orlando Locals Actually Live: A Renter's Guide to the Surrounding Cities
Why fight Orlando's tourist traffic when you don't have to? Explore the best cities surrounding Orlando for renters, with expert tips on commuting, lifestyle, hidden costs, and where to find the most value.

3362 Bougainvillea Dr, Unit 1308

1710 Puritan Ave

151 N Orlando Ave, Unit 207

162 Moyses Rd

3016 Village Hill Pl

4040 Waterview Loop

7039 Pecan Ct

659 Montego Bay Ct

3628 Datura Ct

200 St Andrews Blvd, Unit 316
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.

2866 Euston Rd

1201 Springview Run

5454 Bracken Ct

1855 Eastbrook Blvd

7309 Daniel Webster Dr

1000 S Semoran Blvd

1600 Indiana Ave

4874 Tangerine Ave

3043 Antique Oaks Cir

3651 N Goldenrod Rd
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.

2530 Kamnic Ct

2918 Antique Oaks Cir

3225 Oak Lawn Pl

1695 Lee Rd

3370 Cedar Springs Pl

2704 Tortoise Cv

205 Lewfield Cir

7336 Forest Hill Ct

612 Trinidad Ct

731 W Comstock Ave
Top Neighborhoods Near Orlando Major Employers
Learn about the best places to live near major employers in Orlando with original content written by our Local Expert Darla Ferrara

3367 Riverview Way

5415 Peaco Pl

2510 Roxbury Rd

825 Driver Ave

937 Aragon Ave

1603 Winter Green Blvd

2577 Galliano Cir

5212 N Indiana Ave

151 N Orlando Ave

5117 Lake Howell Rd
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.
Winter Park, FL Local Guide

How much does it cost to rent a home in Winter Park?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winter Park 2 Bedroom Homes for Rent | $1,821 | $1,175 | $2,750 |
| Winter Park 3 Bedroom Homes for Rent | $2,909 | $1,795 | $9,500 |
| Winter Park 4 Bedroom Homes for Rent | $3,627 | $2,100 | $7,995 |
| Winter Park 5 Bedroom Homes for Rent | $6,331 | $2,395 | $9,900 |
| Winter Park 6 Bedroom Homes for Rent | $10,000 | $10,000 | $10,000+ |
Browse Top Homes for Rent in Winter Park
Explore Winter Park
Winter Park, FL Local Guide
- Winter Park Neighborhoods
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10 Hidden Costs of Renting You Should Budget for Before Signing a Lease
Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.
Read ArticleYour 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
Read ArticleNavigating 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.
Read ArticleReal 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.
Read ArticleQuick 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.
Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Winter Park, FL Rentals by Map
See the most popular apartments and homes in Winter Park, FL
Frequently Asked Questions about Winter Park
What type of rentals are currently available in Winter Park?
There are currently 312 Apartments for Rent in Winter Park, FL with pricing that ranges from $529 to $6,500. There are also 216 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $795 to $10,000.
What is the current price range for Rental Homes in Winter Park?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Winter Park ranges from $795 to $10,000 with an average monthly rent of $2,338.
How much are larger Three and Four Bedroom Rentals in Winter Park?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Winter Park range from $750 to $6,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,795 to $9,500. Four Bedroom Single-Family rentals are also available starting from $2,100 and Four Bedroom Apartments start at $1,844.
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

Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!
Written by: Robin Stewart
Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.

Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

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.