Between Orlando And Ocala Is Florida's Oldest Continuously Operating Hotel With Lake Views And Charm

While St. Augustine, Florida, is America's oldest city and is full of historic charm, there are plenty of other important historic destinations in the Sunshine State. Tucked amidst central Florida's idyllic Lake County is the Lakeside Inn, which was built in 1883 and is Florida's oldest continuously operating hotel. The classic inn brimming with charm occupies a scenic, Spanish moss-dotted perch on the shores of the nearly 4,400-acre Lake Dora in the artsy, underrated Florida town of Mount Dora. 

The Lakeside Inn captures the gracious elegance and ease of Old Florida, with its butter-yellow facade trimmed with white and breezy lakefront verandas. Opening in the Gilded Age, the inn was a retreat for Northerners seeking winter sun. Over the years, it has welcomed eminent guests like Calvin Coolidge, who stayed at the inn in 1930, following his presidency. In 1987, the inn earned a coveted spot on the National Register of Historic Places, and — thanks to a full renovation in 2011 — it has been restored to its original glory. Staying at this well-preserved marvel of a bygone era, with its nearly 150 years of hospitality, is akin to stepping back in time, albeit with plenty of modern comforts. Today, the property boasts 90 rooms and suites, as well as multiple restaurants, a lakefront swimming pool, and a beach. 

The Lakeside Inn is easily reachable by a 50-minute drive from Orlando International Airport. Its location between Orlando and Ocala offers convenient access to nearby attractions like Walt Disney World or Ocala National Forest, an underrated national forest for endless recreation. The inn is open year-round, but the best time to visit is the spring and fall months, when temperatures hover around the mid-70s and low 80s.

The Lakeside Inn houses 90 rooms and suites, ranging from smaller queen rooms to spacious suites with parlors, between four historic buildings. While all of the accommodations are airy and painted in pastel hues, there is plenty of beloved Old Florida charm, such as wicker furniture, cozy quilts, and vintage photographs adorning the walls. The top accommodations are the lakefront rooms, which promise lake panoramas from a curved wall of windows. While the interiors are faded, floors and beds are creaky, and there is no elevator, these historic elements are essential to the inn's authentic character. "I truly can't say enough about how charming this place is," raved a Tripadvisor reviewer. "It's romantic, quiet, and incredibly relaxing, a perfect little getaway tucked away in a peaceful, countryside setting."

The inn's main restaurant is The Beauclaire Dining Room, which serves breakfast, lunch, and dinner. Guests can begin the day with Southern specialties, such as biscuits and gravy, fluffy pancakes, or a Southern breakfast sandwich. The lunch menu features generous salads and hearty sandwiches, including the Monte Cristo and the classic Reuben. Dinner is an elegant affair of sophisticated plates with a Southern twist, such as fried green tomatoes or pork belly bites glazed with bourbon, before entrees of filet and lobster tail or slow roasted beef brisket. For dinner with a lake view, opt for a table at The Verandah, where guests can dine overlooking Lake Dora on the colonnaded terrace. More casual meals can be enjoyed at Tremain's Tavern, a cozy, fish camp-inspired pub that serves beer, wine, and historic cocktails, as well as traditional bar food like chicken wings and burgers.

The Lakeside Inn's relaxed rhythm in this hidden corner of Florida is great for leisurely days and active adventures alike. The property's grand lawn is dotted with Adirondack chairs, and it shelters a large swimming pool, making it perfect for a pool day with lake views. Next to the pool is the Waterside Bar, where you can enjoy drinks and snacks throughout the day. Right on the shores of Lake Dora is a petite, sandy beach, which is adjacent to a long dock that extends into the lake. From here, you can embark on pontoon cruises of the idyllic lake and the cypress-lined Dora Canal to learn more about the area's fascinating history and spot some of the lake's inhabitants, from alligators to blue herons. You can also head out on a kayak to independently explore the scenic waterscape or fish for bass in the placid waters.

The inn is also located within a few steps of all the attractions of Mount Dora, which offers movie-set vibes and walkable charm. The town's quaint historic district brims with well-preserved architecture, and streets are dotted with shops, restaurants, galleries, and historic inns. If you want to visit another impressive Mount Dora landmark like the Lakeside Inn, venture about a 15-minute drive from the inn to the sprawling Sydonie Mansion. Originally built in 1883 for a Pittsburgh steel tycoon, the mansion was later redesigned as a grand Mediterranean Revival villa. Today, you can sign up for historic tours of this elegant estate. After a day of exploring Mount Dora, make sure to return to the Lakeside Inn in time for sunset, as the inn's westward-facing position offers spectacular sunset views over the lake.