St. Augustine is one of Florida’s most scenic and historic enclaves.
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Most are already familiar with the city’s long and storied history, which began way back in 1565 when a Spanish admiral set up shop on its shores. Over the years, the historic fort (Castillo de San Marcos) was the scene of many hard-fought battles between European powers like Spain, Britain, and France.
In fact, it’s the oldest continuously inhabited settlement founded by Europeans in the United States.
You can feel that history throughout St. Augustine, in part thanks to its preserved Spanish colonial structures, including its cobblestone streets, and its landmarks, like the fort and the lighthouse. But the city also does a great job of promoting its history with unique activities. The city is a popular stopover during the holidays for its light show, and it also runs an Old Town Trolley year-round.
Toss in some accessible beaches, a small-town pace, and a walkable downtown area, and it’s easy to see why St. Augustine remains one of Florida’s crown jewels.
If you’re looking for a great place to stay for your next visit, start with these Airbnbs in St. Augustine. I’ve rounded up some of the top rentals in terms of location, walkability, and that Old World charm that the city is known for.
Coolest historic Airbnbs in St. Augustine: historic, charming, and walkable
Mulberry 1897
- Built in: 1897
- Sleeps: Four guests in two bedrooms
- Coolest features: You’ve got two free parking spots with this rental, along with an EV charger. It’s also located in the heart of the Uptown district, close to some of St. Augustine’s most sought-after bars, restaurants, and shops. Plus, you can enjoy a private backyard and its large table.
- How walkable is it? Very walkable. You’ve got Uptown stops surrounding the rental, while downtown is a five-minute walk away. The Castillo de San Marcos is less than ten minutes walking.
Blue Heaven
- Built in: Date unknown
- Sleeps: Five guests in two bedrooms
- Coolest features: This rental was fully restored in 2021, meaning you’ll notice a blend of modern and historic features. There’s a large backyard that’s beautifully landscaped. While
- How walkable is it? You’re in the city’s historic district, about ten minutes walking from downtown. Other hotspots, like the trolley stop, are just two blocks away.
La Reverie
- Built in: Late 1800s
- Sleeps: Six guests in three bedrooms
- Coolest features: If you like a little bohemian edge to your historic stays, you’ll love the décor here. There’s a balance of historic features and amenities, along with bright accents that make it feel a bit more vibrant than the other Airbnbs listed here.
- How walkable is it? You’re a bit further from historic St. Augustine in the Lincolnville area—but it’s a historic destination of its own. It was founded in 1866 by the area’s freed Black community.
Triay-Hall House
- Built in: 1807
- Sleeps: Four guests in two bedrooms
- Coolest features: You’re staying in a piece of St. Augustine history at the Triay-Hall House. It was built by Spanish settlers back in 1807 from Menorca in a classic Spanish Colonial style. It has stood the test of time thanks to its unique coquina stone construction and was listed on the Register of Historic Places in 1986.
- How walkable is it? Supremely walkable—you’re in the heart of downtown St. Augustine.
Whitney House
- Built in: Date Unknown
- Sleeps: Six guests in two bedrooms
- Coolest features: You’re on the historic Sevilla Street in downtown St. Augustine, an area most visit. You’ll also notice historic accents throughout, from portraits to wicker chairs.
- How walkable is it? You’re in downtown St. Augustine, so you’ll be able to park your car for days at a time while you explore on foot.
Downtown Abbottry
- Built in: 1910
- Sleeps: Four guests in two bedrooms
- Coolest features: There’s a private courtyard out back where you can enjoy your morning coffee and midnight snacks. The wood features in this home have also been beautifully maintained.
- How walkable is it? You’re slightly removed from downtown St. Augustine, but you can reach the city gates on foot in just five minutes.
Palo Haus
- Built in: 1918
- Sleeps: Six guests in two bedrooms
- Coolest features: There’s a great blend of historic elements with a bohemian design, similar to La Reverie—but less quirky. There’s also free on-site parking.
- How walkable is it? You’re right in the heart of St. Augustine’s historic district. You can walk to major destinations, along with restaurants and shops. You’re also likely to enjoy the historic homes in this area, too.
Stable Keeper’s Hideaway
- Built in: Date Unknown
- Sleeps: Three guests in one bedroom
- Coolest features: This is a loft that once functioned as a stable keeper’s home. It’s part of a hospitality group that runs various properties around St. Augustine, meaning it’s been fully renovated. (Whitney House, above, is part of the same group.) If you enjoy antiques, you’ll love the décor. It gives you a glimpse into the loft’s history as a stable keeper’s residence.
- How walkable is it? You can reach the heart of St. Augustine’s downtown area in just two minutes.
The Schoolhouse
- Built in: Date Unknown
- Sleeps: Six in two bedrooms (plus, a loft for kids)
- Coolest features: There’s a lovely loft setup that kids will love to sleep in, if they aren’t wooed by the bunkbeds in the second bedroom. Plus, this rental comes with a private hot tub in the backyard.
- How walkable is it? You’re in a great spot in Lincolnville, which has its own historic charm and allure. However, you’re a longer walk from downtown St. Augustine.
Big Sisters Cottage
- Built in: 1844
- Sleeps: Five guests in three bedrooms
- Coolest features: If you appreciate a dreamy design that transports you into the past, look no further. This rental is like something out of a design catalogue, heightening its historic charm from every angle. Like the Stabley Keeper’s Hideaway and Whitney House, it’s maintained by a local hospitality group.
- How walkable is it? You’re in the sought-after Uptown neighborhood, which is pedestrian-friendly and close to St. Augustine’s downtown drag.
Cordova Gold
- Built in: 1880s-90s
- Sleeps: Four guests in two bedrooms
- Coolest features: This historic condo was built back in the late 1880s by Henry Flagler to accommodate servants who worked for the local Ponce de Leon Hotel.
- How walkable is it? You’re in the heart of downtown St. Augustine for easy on-foot adventuring.
Historic Downtown Home
- Built in: Date Unknown
- Sleeps: Eight guests in four bedrooms
- Coolest features: It’s gorgeous and large enough that it’s used for small events, from weddings to family gatherings. The finishes are pro, while the antiques highlight the home’s historic charm.
- How walkable is it? You’re in historic downtown St. Augustine, giving you the freedom to walk to the city’s top destinations.
Sevilla Grand
- Built in: Early 1900s
- Sleeps: Six guests in three bedrooms
- Coolest features: You’ve got a mix of modern features with historic touches throughout this home, giving you the best of both worlds. It also has a covered porch where you can watch TV and a gorgeous backyard that feels like a lush, forgotten courtyard from Spain.
- How walkable is it? In a few minutes, you can reach downtown St. Augustine on foot.
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