Cottage holiday rentals in St. Augustine

Unique mid-century modern Lemon Tree Cottage

Bright and cheery Mid-Century modern inspired cottage located in the northern section of St. Augustine. Tucked away on a quiet street, only 2 miles from the heart of historic downtown and 2.5 miles away from the pristine Vilano Beach. All new tile flooring, countertops, fridge and stove, bathroom vanity, linens and area rugs. Meticulously curated to be a unique and fun stay with vintage decor. Great Value Stay for a single family home while being close to downtown. Plenty of off street parking.

~Romantic Historic 1888 Cottage~Walk to Downtown

Come live in history! This cottage traces its roots back to humble beginnings: built by freedmen, it still stands today as one of Lincolnville's original historic treasures. Nestled in the heart of America's oldest city, this endearing historic 1888 cottage offers an intimate, refined escape with a boutique ambiance. This is the ideal retreat for travelers seeking a romantic getaway or guests who wish to be transported to a more graceful time. Discreet in scale but grand in experience.

Driftwood Cottage by the Sea

Great couples' getaway! Beautifully appointed cottage, just steps to the beach. Miles of beaches to walk, run or just sit in place and enjoy. Grocery stores, restaurants and shops a 5-minute walk away. Or, a 5-minute drive into the heart of St. Augustine, a charming Old World town filled with historic sites, unique restaurants, museums and art galleries. Our weather is usually great all year round but don't let a little rain, cold or wind spoil your visit. Adjust your attire accordingly.

Coastal Cottage -firepit, pet fence, kayaks, bikes

Located in the historic Lighthouse Park neighborhood, this charming 1940s coastal cottage is easy strolling distance to the Lighthouse, Alligator Farm, mini-golf, cafes & more! It is only a 0.8-mi walk to the Bridge of Lions, where you can walk over the Bay to downtown St. Augustine. You couldn't ask for a better location! It's on Anastasia Island so you're a short walk/bike/car ride from the beach & Ampitheater. It's cozy, pet & kid-friendly with a big backyard. Kayaks & bikes available!

Fun Waterfront Retreat, Heated Pool, Rooftop Deck

You've found your waterfront oasis tucked under the White Birds of Paradise! This spacious retreat was formerly a commercial art gallery. Two queen beds, one full bathroom & full kitchen make for comfortable living! You have a fenced path leading you down to the beautiful waters of Salt Run where a rooftop deck & salt water in-ground pool invites you to relax and slow down. Less than a mile to downtown St. Augustine, a little over a mile to the Amphitheater and about 3 miles to the beach.

Charming 2/2 Cottage ~ Walk to Historic Downtown

This St. Augustine home is right in the heart of quaint & historic downtown! The lovely two level cottage has an upstairs full bath and two private bedrooms each with a queen bed. Downstairs is a second full bath, as well as a living room and full kitchen. The space is perfect for 1-4 guests. A short 8-10 minute walk allows visitors to explore the many downtown historic sites, museums & restaurants. One parking spot is available on our lot. Free street parking for additional cars.

The Shire on 1 acre marshfront with dock and Spa

One of a kind 1930s historic home, newly renovated and transformed into a beautiful secluded getaway. new luxury finishes, while holding its traditional charm. No Events allowed. Rooftop deck, sunrise views of the Atlantic ocean, Downtown, and sunsets over the river. The new dock with covered roof hosts a national geographic like eco system. It’s short walk to the beach and 3 miles to downtown St George street. Follow along @carcabaroad for weekly content of the home.

Waterfront Retreat | 2 Docks + River Views

Waterfront cottage with views of the St. Johns River, close to top destinations by boat or car! • 3/2 at the start of a peaceful canal • 15 min to Renegades on the water • 20 min boat ride to Lake George • 30 min to Salt Springs by boat • 40 min to Silver Glen Springs • Screened back porch with river view • 2 docks for fishing & tying off boats • 5 min to Shell Harbor boat ramp • Local boat rentals just minutes away • Plenty of parking for trucks & trailers

Couples Boho Bungalow close to Beach and Downtown

Enjoy St. Augustine – the nation’s oldest city – and everything it has to offer from this cozy, Boho themed 1 bed / 1 bath getaway. Located near the heart of the city, it is close enough to walk to the historic St. George Street while also maintaining privacy and quiet comfort. With new, modern amenities, a back porch, a yard, and ample dedicated parking, this home is everything you could want on your trip to beautiful St. Augustine, Florida.