Last Updated on February 5, 2024

Stationed along the picturesque northeastern coast of Florida, St. Augustine stands as a city draped in layers of history and cultural richness. Founded in 1565 by Spanish explorer/colonizer Don Pedro Menéndez de Avilés, it holds the distinction of being the oldest continuously inhabited European-established settlement in the continental United States.  

St. Augustine’s allure as a beautiful destination is woven from a rich tapestry of historical charm, architectural elegance, and natural beauty. The city’s cobblestone streets and well-preserved colonial architecture transport visitors to a bygone era, creating a sense of timelessness that is both enchanting and unique.

The Castillo de San Marcos, a centuries-old fortress overlooking the Matanzas Bay, stands as a formidable symbol of the city’s history and offers stunning views of the waterfront. The historic district, with its narrow lanes, antique shops and inviting cafes, exudes an Old-World ambiance that beckons exploration. Beyond its architectural treasures, St. Augustine boasts pristine beaches, including Anastasia State Park, where sandy shores meet the Atlantic Ocean, providing a tranquil escape for nature enthusiasts.

The city’s commitment to preserving its heritage is evident in the numerous museums, such as the Lightner Museum and the Oldest Wooden Schoolhouse, offering visitors a deeper understanding of its cultural legacy.

St. Augustine’s combination of historical significance, scenic beauty and cultural richness creates a captivating destination that captivates the imagination and invites exploration.

If you love St. Augustine like me or have never yet visited this incredible North Florida coastal treasure, here are some ways to tempt you to come, or return, all offering your own privacy and space. Word of warning: you’re about to fall in love!

Harbor Island Gem in the Historic District

Harbor Island waterfront in the St. Augustine historic district.
Harbor Island waterfront in the St. Augustine historic district. Photo courtesy of VRBO

This waterfront property is located on the edge of the San Sebastian inlet. The one-bedroom, one-bath, 550-square-foot apartment is situated on the first floor of a two-story home with a separate entrance from the upstairs apartment and a screened porch. The apartment can sleep up to four guests with a queen bed and double futon in the common area.

Guests can watch sailboats docked in the harbor and shrimp boats bringing home their daily catch or the tide come in and out along with stunning sunsets.

Harbor Island offers you the feeling of secluded tranquility while only a short walk away from popular restaurants and attractions in the historic district of St. Augustine.  

Coastal Cottage in Quiet Neighborhood

This brand-new (as of 2024) coastal cottage is located in a quaint, quiet, tree-lined neighborhood just a few blocks from the historic district and a 15-minute drive to the beach and Anastasia Island.

The three-bedroom, two-bath home can sleep eight guests: the master with a king, the second bedroom with a queen and a twin bed bunk room. Guests will love the welcoming front porch, gorgeous beach-inspired interior, spacious kitchen and dining room and back patio with a BBQ grill. This rental is ideal for a family getaway!

Uptown Circa 1875 Cottage

Circa 1875 St. Augustine Uptown Cottage.
Circa 1875 St. Augustine Uptown Cottage. Photo courtesy of VRBO

Situated in the center of Historic Uptown, this tastefully decorated and updated 2-bedroom, one-bath bungalow can sleep up to five guests. You’re only a five-minute walk to famed sights such as Castillo De San Marcos and Historic St. George Street in the Colonial Quarter.

The bungalow features an open floor plan with vaulted ceilings, faux wood vinyl flooring throughout, a fenced yard with a deck and plenty of comfortable seating.

Because the home is part of a five-vacation home property, you’ll love having the use of a large year-round heated saline pool with a veranda, sun loungers, dining tables and pool toys.

Island History and Luxury

This charming 1920s fully-renovated luxury 900-square-foot apartment on Anastasia Island is within walking distance to Old Town St. Augustine via the picturesque Bridge of Lions and biking distance to St. Augustine Beach.

The one-bedroom, one-bath apartment is stunningly beautiful and perfect for a short getaway or longer stay. You’ll find everything you need in this vacation rental to make your stay comfortable and memorable.

Historic Downtown Home with Firepit

I have to say that this darling downtown home speaks to me.

It’s not only set in a prime location in the heart of town and walkable to all the fun, but it is part of the Freedom Trail of St. Augustine, and a historic residence that housed some of whom Dr. Martin Luther King named “the heroes of St. Augustine.”

Lovingly renovated, this vacation home integrates its history with a modern style that includes many gathering places. You’ll love enjoying breakfast together on the furnished front and back patios and s’mores around the firepit at night. Kids can run around the enclosed backyard or climb the ladder inside to reach the upstairs loft that features a gaming system and Smart TV. And you’ll appreciate the back patio and lush backyard setting.

The two-bedroom, one-bath abode can sleep up to six guests with one king room and a second that houses four twin beds.

Here Comes the Sun on Anastasia Island

You’re just one block from the water in this two-bedroom, one-bath duplex unit that can actually sleep six appointed with bright island-inspired décor and cozy surroundings. The duplex includes a master bedroom king, guest room queen and a double sofa bed in the living room area.

The good news is that guests are just a walk or drive to downtown St. Augustine, Anastasia Island Beach State Park and nearby restaurants. And remember, you’re only a block away from the picturesque Matanzas River.

Luxe Lemon Loft in Historic Downtown

When you stay in the heart of St. Augustine’s charming historic downtown, you’re in for a real treat. This lovely renovated loft with private entrance features a comfy king bed, posh sitting area, kitchenette and bistro table. And, it’s only an eight-minute walk to the boutique shops, restaurants and top attractions of the city.

The one-bedroom, two-and-a-half-bath loft features mid-century modern stylings and all the amenities you need to make your stay comfortable.  

Boatyard Oasis in Lincolnville

Boatyard Oasis Lincolnville home.
Boatyard Oasis Lincolnville home. Photo courtesy of VRBO

Lincolnville is a neighborhood in St. Augustine established by free men following the American Civil War, designated as a historic district in 1991, and listed on the National Register of Historic Places.

Here’s a beautiful Hamptons-style home just minutes from St. Augustine’s historic district that features a sun-filled living room, gourmet kitchen, three spacious bedrooms, two baths and beautiful outdoor spaces with rocking chairs on the front patio and an expansive rear patio with a lounge and BBQ.

Guests are invited to use the complimentary cruiser bikes and ride or walk to the city’s many restaurants and attractions. When you consider the allure of this 1920s place, the great location and the fact that it can accommodate up to six guests, this is a great place to settle in for your St. Augustine getaway.

Captain’s Home Close to the Beach

This gorgeous stately home featuring two bedrooms and two baths is only minutes to the downtown and to Vilano Beach.

Beautifully furnished, the vacation rental has a large living room, a stunning and well-stocked kitchen, a private backyard patio with BBQ grill, a large front porch and a lower-level area hosting two bedrooms, one with a king bed and the second bedroom with a twin. The sofa also pulls out to a queen bed, so that five guests can comfortably stay in this lovely home.

1919 Historic Modern Craftsman

If you want more space, love history, and having an entire home to yourself, then you’re going to fall in love with this two-bedroom Twin Palms home in Lincolnville.

This 1919 historic Freedom Trail coquina stone home was completely refurbished in 2016. Much more than a remodel, it was a major reconstruction completed with high-end luxury and quality finishes. There are two main-level bedrooms complete with new mattresses and luxury linens. The spa bathrooms showcase Carrera marble showers with glass enclosures and the finest German bath fixtures. And of course, there’s a vintage-era designed claw foot slipper bathtub as well.

The gourmet kitchen features stylish appliances and fully-stocked cabinets and the lovely living area has a double sofa bed.

While you enjoy morning coffee or an afternoon cocktail, you’ll love sitting on the front porch and watching the horse-drawn carriages passing by. The backyard offers a fire-pit table surrounded by Adirondack chairs.

This place is absolutely spectacular!

1919 Vintage Bungalow

1919 Vintage Florida Bungalow.
1919 Vintage Florida Bungalow. Photo courtesy of VRBO

History buffs will also embrace their stay at this 1919 vintage Florida bungalow that’s only a seven-minute walk to the Visitors Center and historic George Street.

The two-bedroom, one-and-a-half bath vacation rental can accommodate up to six guests with the addition of a queen sofa bed in the living room. The home features a large screened front porch and fenced backyard. Hardwood floors and retro-historic details make this home an absolutely charming place for a home-based stay in St. Augustine.

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