Holiday houses in St. Augustine South

2BR/2B Get Away-Walk to St. Aug

This hidden gem (Unit B) is a 2 BR/2 bath home that is part of a duplex within a few minutes walk of some of the best St. Augustine has to offer and a short drive to St. Augustine Beach. The layout is perfect for a family/friends getaway, with the downstairs being comprised of the living area, kitchen, 1 BR, and 1 bath, and 1 additional BR and bath upstairs. 5-min bike ride to the beach, 5-min walk to all the bars and restaurants on Anastasia Blvd, and a 10-min walk(.6mi)to downtown St. Aug.

Winter Hawk Hideout

15 minutes from ol' St Augui. Located in the heart of this typical Florida woods and nested by oaks that saw the Seminole War as we are walking distance from Ft Peyton and 2 miles away from where Osceola was captured. The house sits on half acre of gardens and the decor is ranch, asian and whimsical .The goal is for you to feel transported away for a while. I do have 2 very small, well behaved and quiet dogs and one never seen cat. They do not have access to your quarters or are allowed in.

Chelsea House 3/2, sleeps 6 Free parking Downtown!

Welcome to Chelsea House. Bring your kids, your dog & your boat. It's a sizable 3-bedroom 2 bath rustic style home located on an oversized lot in a quiet residential boating community. If you're looking for something a little different, this is it! It is furnished with an eclectic collection of antiques & reproduction pieces, this home's style will reflect your visit to our nation's oldest city, the home is comfortable, relaxing & private. It is just a 10-minute drive to the Historic District.

Cozy studio 15 mins to beaches & historic downtown

Outstanding location & amenities, 15 minutes to beaches and historic downtown with a quiet, neighborhood vibe. Minutes walk to the intercostal, with piers & boat ramps, gorgeous views, perfect for walks. Close to lots of shopping and dining. Ample parking-trailers & boats welcome. Kid friendly w/ toys, pack & play + more. Very pet friendly as well. Laundry, walk-in shower, private entrance. Private deck w/ cheerful seating. Well equipped kitchenette. Easy drive to theme parks, Daytona + more.

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

St. Aug cottage, great location!

Newly updated tropical cottage close to everything in St. Augustine and steps from the Matanzas River boat ramp. This 2 bedroom, 2 bath home has wood and tile floors and a lovely screened patio to relax looking at nature and listening to the bubbling fountain. Back yard is fully fenced. 3 miles to downtown, beaches, alligator farm, or the amphitheater. Beautiful area for walking along the Matanzas river and your well loved and cared for pets are always welcome. Boat parking available.

BYO Boat, Kayak, Golf Cart, RV

This special place is close to everything & easy to plan your visit to historic downtown or miles of sandy beaches. Located in St. Aug. South with waterfront access to the ICW & waterfront park. Fenced 3/2 can accommodate 12, with use of the OUTDOOR Lanai and air mattress, otherwise 2 king beds and bunk room are available indoors. Plenty of space to park the RV to add extra beds (no hook-ups). Bring your own boat, jet ski, kayak, paddleboard, bikes & golf cart to explore this FL paradise.

Coastal Haven | Quiet River View Near Downtown

😎 Quiet neighborhood ideal for families, walking, & biking ☀️ Stunning sunrise water view 🛏️ Sleeps 8 comfortably 🚗 Short drive 2 beach & historic downtown St Augustine 💥 New Years & 4th of July fireworks visible from just steps away 🍳Fully equipped kitchen for all cooking levels 🔥 Fire pit & Grill ⚽️ Kid friendly space w/ playground and fenced yard 🛜 Fast internet ⚓️Public boat ramp ¼ mile away, bring jet skis, kayaks, & boats 3️⃣➕Days of supplies provided (TP, trash bags, pods…)

Sheepdog Hideway - on Anastasia Island near Amp!

Awesome, private guest suite located on Anastasia Island near the St Augustine Amphitheater! Walking distance to Anastasia State Park! Enjoy staying on the island without all the hustle of a hotel. We have beach cruiser bikes available for use! We are 1.5 miles from the closest public beach access and a 3 mile bike ride to downtown St Augustine! Update for COVID-19 pandemic: We will be spraying all hard surfaces with EPA-approved sanitizer to do our best to make sure surfaces are safe.

St Augustine Entire Home, King Bed, Pet Friendly

Casita Luxe Retreat Near Historic St. Augustine – Pet-Friendly Haven! Discover this luxurious 3-bedroom, 2-bath retreat! Designed with a modern luxe aesthetic, it features custom wood paneling, a fully equipped kitchen with a chic island, and a king-size plush mattress. Enjoy the large, fenced yard, fire pit, outdoor shower, and fun family games. Pet-friendly, with Wi-Fi, smart TVs, and parking included this home offers comfort and style in an up-and-coming neighborhood. Book now!

Art Studio Space – Quiet – Walk to Beach

This very private studio apartment is on Anastasia Island, with its own entrance across the street to Anastasia State Park, which includes the St. Augustine Amphitheater in a quiet, friendly beach neighborhood. This ideal location is quite literally "a walk in the park" to a beautiful undeveloped Florida beach; or a 10 minute drive across the famous Bridge of Lions to historic downtown St. Augustine – with quick access to the many local attractions and great restaurants in the area.

Sunshine Escape! Close to Downtown & Beaches

Sunshine Escape is a charming 2 story home located in West St. Augustine. The location is slightly off the beaten path but still only 2 miles from the Downtown Historic District & 6 miles from our beautiful white sandy beaches! Sleeps 6, 2b/2b + full size sleeper sofa. The large deck & private backyard is a great area to relax, grill & chill. The home is well-equipped with everything you'd need to feel right at home and the entire place is yours during your stay. Come stay with us!