Family-friendly holiday rentals in Anastasia Island

A vibrant cottage exterior is framed by lush green grass and trees, featuring a hammock suspended between the trunks. Colorful seating is arranged near the entrance, highlighting the inviting atmosphere of the backyard oasis.

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

Apartment in St. Augustine

A well-maintained landscape showcases vibrant green grass and neatly trimmed shrubs, with palm trees lining the pathway. An expansive view of the ocean is visible in the background, framed by a boardwalk leading to the beach. Two residential buildings are seen in the scene.

4.99 out of 5 average rating, 198 reviews

SeaPlace, Ocean View, Poolside 2/3 Walk to Beach

Beautiful St. Augustine Beach ocean and pool views from this 2/2.5 townhouse style condo, just steps to the beach. Come enjoy everything this vibrant city has to offer. 2 quiet bedrooms and bathrooms upstairs. 2 private balconies. Downstairs is a full kitchen, dining area for 6 (or well lit workspace), half bathroom, living area w/ new 65" TV, 10 minutes from historic downtown. Family friendly resort community w/ pools, tennis, pickleball and bocce’ ball courts. Beach chairs & towels provided.

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! ✨

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.

The living room is furnished with two light-colored sofas and a central coffee table, creating a spacious and inviting space. A decorative fireplace is framed by mirrors and artwork, while natural light filters in through shuttered windows and greenery adds a touch of nature.

4.94 out of 5 average rating, 221 reviews

Historic Designer Home • Luxury Baths • Steps2DWTN

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.

A charming entrance to a cozy guest suite is framed by lush greenery and wooden structures. A wooden deck leads up to the door, which is complemented by a decorative orange light fixture. The surrounding plants enhance the natural ambiance.

4.96 out of 5 average rating, 194 reviews

MarshMellow-Island Guest Suite Beach Amphitheater

Your own cozy guest suite with private entry. Lovely little bedroom and beautiful bathroom . Private porch and sitting area. Located adjacent our guest studio but the suite is entirely yours and private. These two share a lush garden path, but have separate porches and entrances. The MarshMellow is a well thought out accommodation that has everything we think you'll need for a lovely stay in St. Augustine. A 20 minute stroll to the Amp and short drive or bike to the beaches or downtown.

A modern home with a distinctive triangular roof stands among lush greenery. A manicured lawn extends in front, bordered by palm trees. The building features a combination of light-colored siding and wooden accents, with a small balcony that adds to its architectural charm.

4.99 out of 5 average rating, 130 reviews

Luxury Modern Home in Prime Location 2BDR-3BTH

Book your Spring Break vacation with us! Our contemporary home offers comfort, elegance, and curated amenities. Explore the historic downtown, climb the lighthouse, enjoy live performances, indulge in local cuisine, and relax on the nearby beach. The Lighthouse Beacon is the perfect retreat for families and friends, catering to all preferences. Experience the magic of Saint Augustine and create cherished memories. Book your stay now and let us be your guiding light in this captivating city.

5 out of 5 average rating, 120 reviews

A spacious living area features a light gray sectional sofa with a chaise, positioned on a natural fiber rug. A round mirror enhances the sense of space, while a dining area is visible in the background, complete with wooden chairs and a table.

Villa in St. Augustine

VILLA One

The Villas are designed for short stays, long weekends or for a unique styled location for brands to shoot their products. The space features warm tones, natural finishes and local art for an effortless vibe that allows visitors to relax the second they walk in the door. Complete with two bedrooms, two bathrooms and a backyard complete with tropical landscaping, lounge area, dining and outdoor shower. One of 4 Villas located in St. Augustine Beach. Not pet friendly. @staugustinebeachvillas

Townhouse in St. Augustine

An open living area with wooden beams offers panoramic ocean views through large sliding glass doors. A modern dining table is paired with high chairs, while a cozy seating arrangement features a plush sofa. A mounted TV and decor add warm touches to the space.

4.93 out of 5 average rating, 214 reviews

Penthouse Artist Haven Ocean front Penthouse

Nestled along a pristine stretch of semi-private beach is this historic artists haven offering an absolute beachfront location like no other. This unique home is split into 3 separate floors, where you will be renting the entire top penthouse level. Inside you will find open studio living with a luxe king bed and a front and rear balcony. Enjoy uninterrupted ocean views from the panoramic windows while you relax & watch dolphins play in the surf and stunning sunsets spread across the sky.

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.

A light-filled living area is depicted, featuring a spacious couch positioned against a vibrant artwork of a clownfish. Sliding glass doors lead to a serene outdoor space, while colorful paintings adorn the walls, adding artistic charm to the room.

4.99 out of 5 average rating, 513 reviews

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.

The image captures a serene beach at sunset, where the sun is partially obscured by clouds, creating soft orange and blue hues in the sky. Tall grasses sway gently in the foreground, framing the scene of the calm ocean waves reflecting the fading light.