Holiday rentals with outdoor seating in Historic District, St. Augustine

Balcony apt on USA’s oldest Street (St. George St)

"The Heart of St. Augustine" Voted #1 Airbnb in St Augustine by Trip 101, # 5 Top 10 Airbnb's in St. Augustine" by Territory Supply and in the "Top 15 Best Airbnb's in Florida" by Road Affair. Live music, scrumptious food, craft drinks, and the hustle and bustle of people walking the historic St. George St, all surround you. Relax and people watch from your balcony. Sightseeing, restaurants, trolley stop and nightlife are steps away. This apt is in the center of it all. NYE is a 3 night min

Downtown HistoricLuxury • Designer Kitchen & Baths

Off Street Parking for 2 vehicles 2 Min. walk to St George St 5 Min drive to Anastasia State Park Beach 6 Min drive to Fitness Club/Pool High Speed Starlink Internet Luxury Retreat in Historic Downtown. Indulge in a charming vacation rental featuring a spacious living room, gourmet kitchen, and luxury baths. Immerse yourself in the rich history and vibrant culture, with its charming streets and local attractions. Whether seeking adventure or relaxation, this retreat offers the perfect base.

The Garden Casita in St. Augustine Florida

Secluded garden casita tucked away three tenths of a mile from the city gates. Take the private garden pathway to serenity's doorstep, and gain access to WIFI, free parking, and a kitchenette equipped with the basic necessities. The zen garden serves as a wonderful resting space to relax and unwind from your day. The casita features a queen size bed with luxury linens, desk nook and a full bathroom. Come find your peace at the Garden Casita on the grounds of a 100 year old private home.

Historic St. Augustine 2/2 Duplex & Pool

About this space: Welcome to this 2 unit home located in Historic St. Augustine. This home is close and within walking distance to all the fun downtown has to offer. It is also a short drive to the beaches! This home has 2 bedrooms and 2 full bathrooms, a living room, kitchen, den and direct pool access. This space: This home is a 2 unit house Guest access: There is a lockbox on the door with a key inside Other things to note: Please keep in mind that the pool is a shared space :)

Uptown Classic 1 | Effortless Exploration of STA

Uptown Classic 1 is a 1BD/1BA apartment (2nd floor) that sleeps 2 guests and is located in the heart of St. Augustine. Effortlessly explore the Oldest City with the ease of a 5-min walk to St. George Street - Top sights, local award-winning bars & restaurants surround the home in all directions. The space features cozy, casual interior furnishings and an exterior bistro set. 5-min drive to the beach. Pet-Friendly: Must send message for approval- Pet fee $98 for up to 4 dogs.

Elegant, FREE BIKES dog-friendly downtown apart.

This huge pet-friendly apartment in a beautiful historic house is located only two blocks from the heart of the Old Town and is sanitized between all guests . You will love the first floor spacious bedroom with a very comfortable king-size bed, sofa, and access to the back yard, as well as the large and elegant living room and a full kitchen. Borrow our bikes to roam around town. There is one guaranteed parking space. Pet fee is $40 per dog per stay (max of 2 dogs).

Luxe Lemon Lower in Historic Downtown St Aug.

Stay in the heart of Historic Downtown St Augustine in this 100yr old 2BR/1B completely renovated in 2023! Only a 7 min walk to Downtown a 12 min drive to the beach, you'll love this charming home! Guests should be adults or older children. 1 parking space available. Note: The loft atop this unit is also rentable, w/ connected or disconnected private entrance, & sleeps 2. Ask us or search "AirBNB Lemon LOFT" or "AirBNB Lemon WHOLE" to rent loft or the whole house.

Uptown Classic Bungalow Comfy Walk Everywhere

The Uptown Bungalow is located on a quiet street only a block away from all the action in the heart of the nation's oldest city. Built in 1910 the unit has been renovated, is tastefully decorated ,and is equipped with everything you will need to make your stay in St. Augustine a great experience. Dine in the kitchen or an outdoor patio set on the screened in porch where the guests can enjoy a café & scones in the AM or in the evenings cocktail & Hors d'oeuvres.

Charming 1 Bedroom apt, Historic St Augustine

You will love this newly remodeled one bedroom apartment in Historic St. Augustine. Originally built in 1910 and completely updated in 2023. Just two blocks from St. George St, walking distance to Flagler and all of downtown St Augustine. This apartment offers one bedroom with king size bed, full kitchen and private patio. Free off street parking, so you are able to park, walk around and enjoy everything downtown has to offer.

Short Scenic walk into Historic St Augustine

Stay in Style on Anastasia Island Step into timeless elegance at this fully renovated 1920s apartment. Nestled in the heart of historic Davis Shores, this beautiful retreat blends old Florida charm with modern comfort. 🌴 Perfect Location Walk across the Bridge of Lions to the cobblestone streets, shops, and restaurants of historic St. Augustine. Surrounded by local cafés, parks, and coastal scenery.

Seahorse Studio (Very Walkable + Free Parking)

Located just a few blocks from all that downtown has to offer, the Seahorse Studio is the perfect way to enjoy your trip to St Augsutine. Less than a 10 minute walk to St George Street, the Castillo de San Marcos, the Bayfront, and Flagler College. The studio welcomes you with free off-street parking, a private entrance and yard, and a stylish space to relax after hitting the town.

1900s Cottage in Heart of Town-walk everywhere!

Welcome to Groveside Cottage on the historic street of St. Augustine! In 1920s Grove Avenue was the home of several families of cigar makers and two cigar manufacturing companies. This charming cottage is a great mix of vintage and modern; you will be amused! We allow 1 dog, please message us - approval required before booking. Thank you!