Cottage holiday rentals in St. Augustine

Charming Guest House on Riverfront Estate Weddings

Pretty Guest House situated on majestic 5 acre riverfront estate on the St. John’s River with park-like grounds filled with colorful azaleas, ancient oak and hickory trees, dripping in Spanish moss. Sit back and watch and listen to incredible hawks and bald eagles overhead! Wake up to a magical sunrise each day! Bass Pro Shop did a photo shoot here for their Spring 2025 catalogue! Owners home is on the property and they are always available. 45 minutes to JAX Beaches. 35 min to St. Augustine.

Walk Historic Downtown! “Blue Heaven”

Stunningly renovated cottage combines modern amenities with vintage charm... * 2 master suites with queen beds * Quiet neighborhood walking distance to explore The Nation's Oldest City * Clawfoot tubs inside and out (along with showers, of course!) * Big screened-in porch with hanging daybed * Off-street paved parking * Fully fenced backyard, Weber grill, gas fire pit * Fast Wi-Fi and Smart TV * 2 blocks to Fish Camp, Ice Plant, LaNuvelle, trolley stop * 10 minute walk to central downtown

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!

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.

Location! Stylish Downtown Cottage Getaway

Charming and centrally-located 2 Bedroom Cottage. Only a 12 min walk to the Historic Core so park your car and enjoy a beautiful stroll Downtown! After a day spent sightseeing you will appreciate the comfort of this little getaway. The open floor plan w/vaulted ceilings in the main space has a well equipped Kitchen, Dining space, Living Room w/TV plus work space. Two comfy Queen Beds w/TV and a roomy walk in shower round out the space. Relax on the porch swing or patio w/fenced yard.

~Romantic Historic 1888 Cottage~Walk to Downtown

Come live in history! This cottage traces its roots back to humble beginnings and it still stands today as one of Lincolnville's original historic treasures. Nestled in the heart of America's oldest city, this endearing circa 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. Modest in scale but grand in experience.

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.

Downtown House near Flagler College & St George st

Enjoy this charming, (originally a carriage house in 1899) adorable cottage, nestled in the heart of historic downtown St Augustine! It's a rare find for its proximity. Walking distance to all of downtown and Flagler College! No driving necessary for a full complete vacation. This amazing little house has a fully stocked kitchen that opens up to a shaded deck. We do require guests be 25+ to book instantly otherwise please inquire. Please read the whole listing.

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.

Tones of Blue

Just a short walk to one of St Augustine's loveliest beaches, this completely renovated 2-bedroom, 2 bath beach cottage is sharp to say the least! Well appointed with a full kitchen, washer dryer and 2 king beds. Lots of parking and a fenced outdoor seating area. Quiet neighborhood close to downtown. There is also a detached garage apartment available to rent for additional guests. Sorry but no pets or smoking

Cane Cottage Oceanfront Oasis

Cane Cottage was renovated in 2018-2019 after extensive damage from multiple hurricanes. Our vision was to bring this old Florida beach cottage back to its original charm while also adding new life and modern amenities. From the outdoor entertaining spaces to the lavish interior finishes this AirBnB makes for the perfect beach retreat. Well designed and functional home with many well-thought-out touches.

1920s Coastal Cottage | Walk to Amp & Downtown

Light-filled, historic charm meets modern coastal living. Built in the 1920s, this meticulously updated 2-bedroom, 1-bathroom cottage features original heart pine floors, walls of windows, and a breezy, open feel that instantly makes you feel at home. Nestled in the quiet, historic Lighthouse Park neighborhood, you are right between the beach and historic downtown — 5 minutes to both.