Some people only come to Orlando for the theme parks, but for those who crave something different—one rich in art, upscale independent shops, and quiet, natural landscapes—the swanky community of Winter Park is the right answer. It’s the kind of place where a well-heeled crowd hangs out, with not a Mouse ears headband in sight. This charming enclave was the winter retreat of the famous sweater-wearing Mr. Rogers, and its tree-lined brick streets will tempt you to hum his signature song about a “beautiful day in the neighborhood”—seriously, you’ll have major house envy as you drool over the storybook mansions.
At its heart stands The Alfond Inn, a refined boutique hotel that blends sophisticated hospitality with museum-quality contemporary art. Every gleaming corridor doubles as an art gallery, featuring ever-evolving pieces from The Alfond Collection of Contemporary Art, from the large-scale oil paintings and prints in the lobby to the mirrored geometric works that dazzle in the sunlight streaming through the atrium. With lush courtyards for sipping coffee or wine, a pampering spa, two pools, and an easy walk to Park Avenue’s best boutiques and cafés, you’ll forget about the madness of the theme parks just 30 to 45 minutes away.
Why stay at The Alfond Inn?
Even if you’re not an art lover, you’ll still be in awe of this living art museum with more than 130 works in all mediums, including photography, video, sculpture, and motivating affirmations. You can also feel good about staying here: the hotel is owned by the nearby liberal arts school, Rollins College, and its net income goes directly to fund college scholarships—no other hotel in the world is set up this way. Guests can even take part in 60-minute art tours on the first Wednesday of every month.
The hotel recently underwent a complete renovation, and every inch literally sparkles—like a real museum, it’s kept clean as a pin. Expect to share the space with couples, low-key friend groups, business travelers during the week, and wedding parties on the weekends (along with parents visiting their Rollins students).
It’s not uncommon to see people working at communal tables and nooks surrounded by art, and the rooftop pool fringed with palm trees is a slice of peaceful heaven. Another major perk is its prime location, set within a residential neighborhood made for tranquil daily strolls. And pretty much year-round, there’s almost always a festival or event happening right in town.
What are the rooms like at The Alfond Inn?
Spotless and drenched in joyful hues of yellow and turquoise, all of the rooms were completely gutted less than two years ago, so they feel brand new. There’s a good mix of classic rooms with various layouts, along with suites catering to business travelers and those who want extra space.
I stayed in one of the luxury suites, which felt more like an apartment—with a kitchen equipped with full appliances (prettier than my own at home), a separate living area with a couch big enough to stretch out with others in front of the TV, a dining area, and indulgences like a soaking tub. It was the kind of room you look forward to returning to at night.
What are the best things to eat and drink at The Alfond Inn?
Hamilton’s Kitchen is the hotel’s signature restaurant, and it’s all about Southern hospitality and cuisine. Start your morning with breakfast on the outdoor terrace, accompanied by the trickling sounds of the nearby fountain and maybe the chiming of the school bells. You’re on vacation, so order the breakfast breads topped with fresh berries—which naughtily feel like dessert—and Executive Chef Michelle Gomez’s favorite dish, the Hamilton’s Frittata made with goat cheese, asparagus, skillet potatoes, and drizzled with chili oil.
At night, go for the cornbread made from the chef’s family recipe she grew up with (the cream corn is the secret ingredient), paired with whipped orange blossom honey butter, a bowl of chicken and dumplings, and the daily fish—mine was Hawaiian-style with pineapple.
When you’re ready for a change of scenery, stroll over to Park Avenue for top restaurants like Ava MediterrAegean, the Briarpatch Restaurant (just look for the long lines, especially at weekend brunch) and AJ Chocolate House.
What is the service like at The Alfond Inn?
Excellent. From the restaurant to the front desk and the spa attendants, everyone is genuinely focused on making your stay better.
What are the gym, pool and spa like at The Alfond Inn?
Arrive at the spa to slip into a plush navy robe and take advantage of the amenities, including a sauna, steam room, heated loungers, and an experience shower that hits and massages you from multiple angles. I also loved the daily salt scrub they leave beside the showers (mine was a coffee scrub that left my skin baby-soft). I had an 80-minute Radiance Renewal facial where the practitioner used everything from gua sha to massage and masks to give me glowing skin. With tip, it’s a splurge at $300-plus, but for me, the spa amenities were worth it.
There are two pools: a rooftop pool for all guests and another at the spa, which is quieter and reserved for spa guests only. The gym is huge, with a Peloton bike and every machine imaginable for a solid workout—but I also suggest getting up early to walk the scenic neighborhood for your exercise.
What’s the area like around The Alfond Inn?
Dreamy, just like you’d expect Mr. Roger’s neighborhood to be. You’re a five-minute walk to posh Park Avenue, which is lined with high-end boutiques, shops and restaurants. You’re also a three-minute walk from the Winter Park Scenic Boat Tour, a $20 cruise through the chain of lakes and canals, past mega-mansions and natural scenery. If you didn’t get enough art peeping at The Alfond, there are several museums to explore, including the Rollins Museum of Art and The Charles Hosmer Morse Museum of American Art, home to a dazzling collection of Louis Comfort Tiffany’s famed glass lamps, windows, and art glass.
Why you should book a stay at The Alfond Inn
For those who want to experience a chic and culturally charged side of Orlando, The Alfond Inn caters beautifully to romance, friends’ getaways, wedding parties, and business travelers. You won’t miss the crowds—and it just might inspire you to house-hunt in the area. Winter Park, and the hotel, is Orlando’s quiet masterpiece.
DETAILS
Address: The Alfond Inn 300 E. New England Park, Winter Park, FL 32789
Price per night: Off-season rates start at $269, with peak season rates starting at $469
Closest transport: Orlando International Airport is a 45-minute drive
Book now: via Booking.com
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