Cottage holiday rentals in St. Augustine

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. Ask about our AM Coffee service

Little Sister's Carriage House w/ Parking

Welcome to Little Sister's Carriage House, a bright and delightful historic cottage located only steps from all St. Augustine has to offer. Beautifully furnished and full of vintage touches, this home is the perfect blend of modern comfort and historic charm. With a personal garden, full vintage kitchen and tons of character, it's a one of a kind stay. Sip coffee on your porch, or take a short stroll into town. Park your car and walk everywhere! Locally operated by lifelong St. Augustinians.

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.

119 Kings Ferry Way Historic Cottage

Absolute treasure in the heart of the Lincolnville Historic District. Ideal private and peaceful location within walking distance of great restaurants and historic sites, and FREE on site parking. Our other two side-by-side Cottages are available for groups of up to a total of eight adult guests who want to be in close proximity but also want privacy. Experience one of the most authentically restored century old cottages in the area. Perfect for extended stays or short visits.

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.

Enchanting courtyard, quiet cottage by beach

Very comfortable, relaxed island breezy appeal. King and queen bedrooms, additional quality blow up queen mattress. Open living space with French doors leading to back deck. Spacious kitchen, dining & breakfast nook. Gorgeous private courtyard with string lights for magical night time ambiance. Expect everything you may need with complimentary wine and baked goods upon arrival. Local dining scene is incredible! No smoking inside! *See house rules for pet info.

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.