The Alfond Inn

300 East New England Avenue

Just 10 minutes from downtown Orlando, in village-like Winter Park, the Alfond Inn has a unique legacy: The boutique lodging was created to provide income for scholarship funds at neighboring Rollins College, one of Florida’s oldest liberal arts schools. If helping students isn’t reason enough to book a stay, the hotel offers lots more incentive. A skylit domed atrium in the Spanish colonial–inspired main building draws your eye to a rotating collection of artwork curated by Cornell Fine Arts Museum, and pet-friendly guest rooms are simple and cheerful. While the hotel is not a full-fledged resort, it offers guests plenty of opportunities to linger. Fire pits and rocking chairs are dotted around the property, and shaded areas for loungers enhance the rooftop pool’s already undeniable appeal. Hamilton’s Kitchen restaurant serves modern Southern cuisine paired with wines selected by an award-winning sommelier. And shops, wine bars, and independent boutiques like Rifle Paper Co. line the town’s Park Avenue, a few blocks away. You can also take a pontoon boat tour for views of many of the Mediterranean-style mansions along the waterfront. Perhaps best of all, Disney and Universal theme parks are only a half-hour drive away.

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