Holiday rentals with a fire pit in Anastasia Island

4.94 out of 5 average rating, 129 reviews

Entire House & Backyard Oasis - WALK TO BEACH

PARADISE ON PALMETTO 2: Unwind by the waves or at home in the backyard oasis. A true beach escape, we are nestled between the Atlantic Ocean & Intracoastal Waterway, walking distance to the beach & river. This bright, remodeled 1-Bedroom cottage is two blocks from the ocean and a 15 minute drive to restaurants, bars, and attractions in Historic Downtown St. Augustine. Experience this ideal base to explore the Nation’s Oldest City! PARKING & WASHER/DRYER INCLUDED. SUPER CLEAN. NO CONTACT CHECK-IN

4.98 out of 5 average rating, 182 reviews

Uncle Reggie's Beach House

🏝️ Welcome 2026 Spring & Summer guests to your PRIVATE beach house! Walk to the beach, restaurants, arcade, coffee & yoga. 10min drive to historic downtown St. Augustine. Fenced yard, covered deck, grill, fire pit+ luxe outdoor shower. 3 bed/2 bath, sleeps 6. Kid/pet friendly. Modern kitchen. Remote workspace. 65" TV. ORIGINAL NINTENDO & 650+ games. 2 bikes, 2 chairs, + beach cart. Free coffee. Peaceful & quiet street yet close to everything. Always 5-star service hosted by hospitality pros! ✨

Guesthouse in St. Augustine

A private cottage exterior features a deck with outdoor seating under an umbrella. Adjacent lounge chairs provide a place to relax. The structure is surrounded by grass and mature trees, with a small grill visible nearby.

4.88 out of 5 average rating, 181 reviews

Island’s Edge Guest Cottage on Anastasia Island.

Fresh and professionally cleaned marsh front private cottage with amazing views. Walk or pedal from this adorable cottage to any of the local attractions. Nestled between the state park, our famous AMP, great beaches & downtown. Everything is close by. Your deck is perfect for a bbq, bird watching & sunset cocktails. ☹️Sorry no marsh access.☹️ Park trails and beach are close by. Stroll over to the Saturday morning market at “the Amp”. Ask me about our “Concert Package” You’ll love it here.

The exterior of the two-story property is shown, surrounded by lush greenery and trees. A spacious gravel driveway leads to the home, which features a covered porch on the upper level. The lower area includes a decorative railing and opens up to a well-maintained yard.

4.89 out of 5 average rating, 111 reviews

Tree Tops: Where Everything is brand new

Take it easy at this unique and tranquil getaway nestled in the Tree Tops. All new appliances, furniture, electronics, sheets, and towels are found in this totally remodeled home. No expense was spared in making your stay as comfortable as possible. This is your perfect get away from the hustle and bustle of life. Enjoy your first cup of coffee on one of 3 porches. Tree Tops is also close to popular attractions, located 6 miles to Vilano Beach and 4 miles to St. Augustine’s historic district.

5 out of 5 average rating, 269 reviews

A charming two-story cottage is seen behind an ornate wrought-iron gate, framed by vibrant green grass and well-maintained landscaping. Large windows allow natural light to fill the exterior, and a cheerful yellow door adds a welcoming touch.

Cottage in 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

4.92 out of 5 average rating, 225 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!

Holiday home in St. Augustine

4.98 out of 5 average rating, 148 reviews

Guest Favorite: 2BR, Walk to Beach, Fenced Yard

Welcome to Turtle Cove A — a freshly renovated Saint Augustine Beach duplex just a 2-minute walk from the sand. Whether you’re sipping coffee on the private balcony, lounging by the chiminea in your fenced backyard, or rinsing off in the outdoor shower after a salty swim, you’ll know you’ve stumbled onto something special. Stylish, calm, and actually walkable to the beach. (Yes, for real. You can see the beach access from the road.) We also host Turtle Cove B next door. Check it out too!

Guest suite in St. Augustine

4.95 out of 5 average rating, 782 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.

4.97 out of 5 average rating, 116 reviews

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!

A wooden walkway leads from a grassy area to the sandy beach, flanked by two benches on either side. The beach is visible in the distance, with gentle waves and a clear blue sky above.

4.95 out of 5 average rating, 305 reviews

St Augustine Beachside Home - Walk to Beach

Relax at our St Augustine Canal-front getaway! Great family destination just 15 min. to Historic Downtown St Augustine. Neighborhood features PRIVATE Beach Access with about a 10 minute walk to the Beach. Boating and Fishing at your Fingertips with private, over-the-water dock and ramp to floating dock where you can tie up your own boat/kayak/jet skis. The perfect end to your beachside dream day will be watching the sunset while on your private dock.

5 out of 5 average rating, 101 reviews

Boomerang Bungalow

Cozy, quiet retreat on Saint Augustine's Anastasia Island! Come enjoy your stay at this totally updated, modern, mid century bungalow. Walk across the scenic Bridge of Lions to historic downtown Saint Augustine with its many great restaurants, museums, art galleries and shops. Only a mile from the beach at Anastasia State Park and a short drive to the beautiful, white sand beaches on Anastasia Island. Bicycles available for guest use upon request.

Aerial view of a home surrounded by lush greenery near a waterway, featuring a long dock extending into the water. The structure is illuminated, highlighting the inviting exterior against the twilight sky.