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Luxury Homes for Rent in Winter Park, FL (116 Rentals) Page 3 of 3
The most luxurious Homes in Winter Park with high-end amenities, features, and finishes.
544 N Bumby Ave
OrlandoFL32803
206 Quayside Cir
MaitlandFL32751
1112 Chichester St
OrlandoFL32803
201 Cedarwood Dr
MaitlandFL32751
266 Park Lake St
OrlandoFL32803
266 Park Lake St
OrlandoFL32803
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1907 Garvin St
OrlandoFL32803
1610 Lyndale Blvd
MaitlandFL32751
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$5,4693 Bedroom Apartments Available Mar 5, 2026
1610 N Goldenrod Rd
1610 N Goldenrod RdOrlando, FL 32807
218 Park Lake St
OrlandoFL32803
218 Park Lake St
OrlandoFL32803
3260 Lake Shore Dr
OrlandoFL32803
281 Shell Point E
MaitlandFL32751
281 Shell Pt E
MaitlandFL32751
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 | $1,931 | $875 | $4,850 |
| Winter Park 3 Bedroom Homes for Rent | $2,671 | $1,395 | $5,650 |
| Winter Park 4 Bedroom Homes for Rent | $5,141 | $2,100 | $10,000+ |
| Winter Park 5 Bedroom Homes for Rent | $10,130 | $2,450 | $10,000+ |
Browse Top Homes for Rent in Winter Park
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Frequently Asked Questions about Winter Park
What type of rentals are currently available in Winter Park?
There are currently 306 Apartments for Rent in Winter Park, FL with pricing that ranges from $850 to $6,050. There are also 322 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $800 to $25,000.
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 $800 to $25,000 with an average monthly rent of $5,055.
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 $1,099 to $6,050, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,395 to $5,650. Four Bedroom Single-Family rentals are also available starting from $2,100 and Four Bedroom Apartments start at $3,150.
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
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.
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.
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.
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
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.
Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.