Historic Homes with Plenty of Character: Distinctive Rentals for Your Next Getaway
Original wood floors, a welcoming front porch, rooms with a story to tell. Some vacation homes become a memorable part of the trip before you’ve even unpacked.
For travelers who love architecture, older neighborhoods and places with personality, a historic rental offers another way to experience a destination. These distinctive iTrip homes pair details from the past with comfortable spaces for settling in, whether you’re spending a weekend in Charleston or exploring the streets of St. Augustine.
Cedar House on East | Annapolis, Maryland
Cedar House on East has lived several lives. Built in the late 18th century, the three-story home has served as a shoemaker’s store, an inn and the residence of an Italian immigrant who performed in the U.S. Naval Academy band.
Today, it welcomes vacationers as a restored single-family home. Original wood floors carry that history through the interior, while renovated living spaces give guests room to relax between outings in downtown Annapolis. It’s a fitting choice for anyone who finds themselves wondering about the stories behind the buildings they pass.
Liberty Tree House | Charleston, South Carolina
A private courtyard gives Liberty Tree House an appealing place to pause between Charleston adventures. Have breakfast outside, head out to explore, then return for a quiet dinner after a day around town.
Located in Charleston’s historic Garden District, this renovated home features hardwood floors, shiplap walls and beamed ceilings, along with an updated kitchen. Two upstairs suites provide room to spread out, and nearby attractions include the Charleston Museum, Marion Square and the South Carolina Aquarium. For travelers who enjoy filling their days on foot, there’s plenty within walking distance.
Little Yellow Cottage on Water Street | St. Augustine, Florida
The name alone makes this cottage easy to picture. Add a large front porch, restored original hardwood floors and a fenced courtyard, and you have an inviting home base for an Old City getaway.
This early-1900s cottage sits near the Matanzas River, within walking distance of Castillo de San Marcos and downtown attractions. Inside, historic and retro details give the rooms personality. Outside, the porch and courtyard offer two tempting spots for morning coffee or a little downtime before dinner.
Spend the day browsing shops and exploring St. Augustine, then take the scenic route home along the waterfront.
Explore Little Yellow Cottage on Water Street.
Casa Grande | Tampa, Florida
If your ideal getaway includes city exploring and a front porch to come home to, take a look at Casa Grande. This restored Craftsman bungalow sits between Ybor City and Tampa Heights, putting local dining, historic cigar shops and waterfront outings within easy reach by car.
The two-bedroom home sleeps four and combines classic architectural character with updated interiors. Its private front porch is a highlight: a comfortable place to start the morning slowly before heading to Armature Works or the Tampa Riverwalk.
Casa Grande is one of three separate rentals on the property, with its own entrance and exclusive front porch.
Historic Hideaway | Annapolis, Maryland
Follow the brick sidewalks along Prince George Street to Historic Hideaway, a renovated home dating to the late 1800s. Its location in Annapolis’ Historic District makes it especially appealing for travelers who want to explore downtown, the U.S. Naval Academy and nearby waterfront sights.
Back at the house, a double-sided gas brick fireplace connects the living and dining rooms. The backyard adds another gathering space, with outdoor dining, lounge seating and a fire pit. Plan a day of sightseeing, pick up something for dinner and leave time to enjoy the house itself.
1 Fletcher Lane | St. Augustine, Florida
Built in 1920, this Colonial Revival cottage offers a comfortable base for exploring downtown St. Augustine. Hardwood oak floors and personal touches throughout the renovated interior give it a warm, lived-in feel.
Two bedrooms accommodate up to four guests, making it a good option for a small family or two couples. There’s a full kitchen for meals at home, space for games or puzzles, and a back deck in the fenced yard. A private driveway lets you leave the car behind while you walk to downtown shops, restaurants and historic attractions.
When you’re ready for a change of scenery, St. Augustine Beach and Anastasia State Park are a short drive away.
Find a Stay with a Story
The home you choose can shape the whole trip. A courtyard becomes your breakfast spot. A front porch gives you a reason to linger. An original floor or centuries-old facade sparks a question about who was there before you.
For your next getaway, make room for a little history. Explore these distinctive rentals or browse iTrip destinations to find a stay with character all its own.