Holiday rentals with a fire pit in St. Augustine South

Guest suite in St. Augustine

4.98 out of 5 average rating, 477 reviews

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.

Superhost

4.88 out of 5 average rating, 149 reviews

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.

Treehouse in St. Augustine

4.93 out of 5 average rating, 521 reviews

courtyardtreehouseinthehistoricdistrict

You have found your cozy oasis tucked in a (Real) Treehouse lodged in Ancient Oak. Set in a lush tropical garden in the historic district. It’s a minimalist’s dream, exemplifying the appeal of tiny living: compact, clean, efficient and 2 1/2 blocks to the historic districts shopping and restaurants. Relax on the Sun Deck, Rain Deck or in the Courtyard’s Tropical Garden The day time peaceful beauty is only eclipsed by the the nighttime display of laser lights projected onto the oaks canopy.

4.97 out of 5 average rating, 154 reviews

Home in Lincolnville

LUX Riberia – 311 | 12-min walk to Historic DTN

LUX RIBERIA COLLECTION - Contemporary, architectural magnificence located in the heart of the eclectic Lincolnville neighborhood in Downtown St. Augustine. Effortlessly explore the Oldest City with a quick 12-min walk into the Historical Downtown for all the top sights, hottest bars & restaurants. Two-story, minimalist style home with double heighted ceilings, fits 6 guests spaciously across the 2 BD, 2.5 BA layout with fully fenced backyard. Views of San Sebastian River perfect for Sunsets.

4.92 out of 5 average rating, 180 reviews

Cottage in St. Augustine

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!

4.97 out of 5 average rating, 113 reviews

Coastal Haven Mins 2 Town & Beach

😎 Quiet neighborhood ideal for families, walking, & biking ☀️ Stunning sunrise water view 🛏️ Sleeps 8 comfortably 🚗 Short drive 2 beach & historic downtown St Augustine 🍳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…) 💥 4th of July & New Years fireworks visible from just steps away

4.87 out of 5 average rating, 196 reviews

Ocean Front Private Getaway in St. Augustine Beach

Just steps from the ocean and a 10-minute drive to historic downtown St. Augustine, this one-of-a-kind 1970s pink three-story A-frame is the perfect backdrop for your next vacation, bachelorette party, or relaxing getaway. Inside, you’ll find a bright, cheerful space—ideal for popping mimosas in the morning or unwinding after a sun-soaked day with private beach access. Whether you're staying for the weekend or the season, you're sure to make lasting memories. I can’t wait to host you!

Guest suite in St. Augustine

4.95 out of 5 average rating, 699 reviews

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.

5 out of 5 average rating, 218 reviews

Cottage in Lincolnville

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 * Fenced yard, Weber grill, gas fire pit * Fast Wi-Fi and Smart TV * 2 blocks to Fish Camp, Ice Plant and LaNuvelle * 10 minute walk to central downtown St Augustine

Campervan/RV in St. Augustine

4.9 out of 5 average rating, 163 reviews

Scarlett Ruby

Meet Scarlett Ruby! Situated 2 blocks from St. Augustine intercostal waterway. Bring your boat, fishing rods, paddle boards or kayaks and launch at one of the 2 boat ramps in the neighborhood. Looking for sightseeing? Visit Historic Downtown St. Augustine with world class dining and shopping along St. George St. Just 10 min from Scarlett Ruby. Or relaxed at beautiful St. Augustine beach also just 10 mins away. Something for everyone! Come visit Scarlett Ruby in the Ancient City!

4.99 out of 5 average rating, 204 reviews

HistoricLuxury•Designer Kitchen&Baths•Walk&Trolley

No Cleaning Fee! 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 3-BR Retreat in Historic Downtown. Indulge in a charming vacation rental featuring a spacious living room, gourmet kitchen, and luxury bath. 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.