Orlando, Winter Park Rank Among Nation’s Best Places to Live and Learn
WalletHub names Orlando the No. 3 Best College Town in America and ranks Winter Park the No. 1 small city in Florida and in the top 20 nationwide for quality of life.
November 07, 2025
Orlando and Winter Park continue to shine as a premier destination for college students and residents alike. In its latest national rankings, personal finance website WalletHub named Orlando the No. 3 best college town in America and Winter Park the No. 1 small city in Florida and a top 20 spot nationwide for quality of life.
WalletHub’s annual Best College Towns in America ranking compared more than 400 U.S. cities based on 31 factors spanning affordability, academic opportunity, and social environment. Only minutes away from Rollins, Orlando stands out for its strong combination of accessible higher education (ranking 54th among the more than 400 cities in WalletHub’s study for school quality), dynamic culture, and robust job market—key advantages for both students and young professionals.
“Orlando has a great economy,” notes WalletHub, “with one of the lowest unemployment rates and the 16th-highest job-growth rate in the nation, so it’s a great place to stay and work even after graduation.”
The city also earned high marks for its abundance of entertainment options—from food trucks and coffee shops to major sports, world-renowned theme parks, and performing arts venues.
“Picking the right college is crucial, but it’s also important to make sure that the surrounding college town will be a place where you’ll truly love spending your college years,” says Chip Lupo, WalletHub analyst. “Towns with a low cost of living, plenty of activities and large student populations can make your college experience a lot less stressful and a lot more enjoyable. In addition, cities with a great economic environment can make it easier to get a job during or immediately after college.”
Just north of Orlando, Rollins’ beloved hometown of Winter Park earned No. 1 small city in Florida and placed No. 19 nationally for quality of life in the Best Small Cities in America ranking, which assessed more than 1,300 cities across five categories: affordability, economic health, education and health, quality of life, and safety.
Winter Park—the quintessential backdrop for the Rollins experience—continues to stand out as one of Florida’s most desirable small communities, celebrated for its charm, safety, livability, vibrant cultural scene, walkable downtown, and abundant green spaces.
Having attended a small boarding school for high school, Ava Bartolomucci ’28 knew she wanted a close-knit college experience that would allow her to explore new interests, build meaningful relationships, and take advantage of a vibrant new setting. Since arriving at Rollins, she’s found exactly that in the heart of Winter Park and nearby Orlando.
“I love going to Disney on the weekends—it’s only about 30 minutes away,” she says. “I also love grabbing coffee at one of the local cafes on Park Avenue with friends, checking out the shops, and trying out new restaurants. It’s the perfect way to vibe with new people and explore the area.”
Together, Orlando and Winter Park’s strong showings reaffirm Rollins’ reputation as not only a hub for higher education but also one of the nation’s most vibrant, welcoming places to live, learn, work, and thrive.
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