House 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, 131 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

An expansive backyard features a refreshing saltwater pool and a hot tub, surrounded by lush turf landscaping. A two-story building with a wooden staircase overlooks the serene outdoor space, framed by palm trees and vibrant plants. Lounge chairs are positioned nearby for relaxation.

4.99 out of 5 average rating, 153 reviews

Driftmark Cabin - RV friendly, Pool + Beach!

Experience the ultimate beachside getaway at our fully renovated Airbnb, just steps away from the sun-kissed sands. This luxurious retreat offers modern comfort with a private pool and inviting hot tub, allowing you to unwind in style. The recently upgraded interior boasts premium amenities, ensuring a relaxing stay. Outside, lush turf landscaping surrounds the pool, creating an oasis of comfort. Whether you're lounging by the pool, or enjoying the beach a stone's throw away, Driftmark delivers.

4.98 out of 5 average rating, 186 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 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, 225 reviews

Downtown • Historic Whitney House • Luxury 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.

A modern home is surrounded by a well-kept backyard featuring a private pool and spacious patio. Comfortably arranged lounge chairs provide a relaxing spot. The exterior showcases light-colored siding and elevated balconies, with palm trees dotting the landscape for a tropical feel.

4.89 out of 5 average rating, 106 reviews

Sunset Cove 2 - Pool - Sea Views - Walkable

Stunning new luxury 2br/2.5ba pool home with peeks of Salt Run and Anastasia State Park: * Pool Heat Available for $30 per day - Contact us after booking for details * Private pool + backyard * Parking for 3 cars * 2 king bedrooms w/ en-suite bathrooms & smart TVs w/ Netflix * 2 min drive (or 20 minute walk) to historic downtown St. Augustine * 2 min drive to the beach (Anastasia State Park) * 5 min walk to lighthouse, Alligator farm, restaurants & bars * Fully stocked and equipped kitchen

The living area features a modern design with custom wood paneling on one wall. A leather sofa is positioned in the foreground, while a decorative coffee table and a small workstation with a chair are visible. Soft lighting highlights a piece of scenic artwork above the table.

4.97 out of 5 average rating, 122 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, 312 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.

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.

4.99 out of 5 average rating, 148 reviews

Gorgeous Views, Golf cart w/beach access!

Beautiful home with outstanding view & access to the Intracoastal. Watch dolphins play, yachts cruise by or catch the sunset from the dock. If you're feeling adventurous, jump on a kayak or paddle board & explore the quaint islands nearby. If the ocean is calling, take a 2 min ride with the included 6 seater golf cart (must sign waiver) & drive right on to Crescent beach. Grab a surf or boogie board for some extra excitement!

A dining area is featured with a blue table at its center, surrounded by four wooden chairs with woven seats. Natural light filters through bamboo shades on the windows, highlighting a wooden sideboard displaying beach-themed decor.

4.97 out of 5 average rating, 150 reviews

Perfect One Bedroom Cottage in Lighthouse Park

One bedroom one bath cozy cottage vibe! Perfect couples retreat. This is one half of a duplex. The second half is currently vacant. Excellent location. 5 blocks to the lighthouse. 1 mile to historic downtown. 1.3 miles to the Amphitheater. 0.8 miles to Anastasia State park. 3 miles to the St. Augustine Beach Pier. Walking distance to many great restaurants and bars, mini golf, and boutique shops! Walk or bike to downtown!

A comfortable living area features a large sectional sofa adorned with yellow and grey cushions. A flat-screen television hangs above a decorative fireplace. A coffee table with a small plant is centered on a textured area rug, and natural light filters through the nearby windows.

4.91 out of 5 average rating, 327 reviews

SaraCasa - First Floor House 2Br/1.5Bath

Forget your worries in this spacious, serene, and comfortable property. This totally remodeled house was built in 1910 and is walking distance to literally everything in downtown St Augustine. The best part of the property is that it is walking distance to everything, but still far enough from downtown to enjoy a peaceful evening at home.

A refreshing pool awaits in a spacious backyard, framed by vibrant greenery. A colorful mural of 'FLORIDA' adds a cheerful touch to the exterior, while comfortable chairs are positioned nearby for relaxation. The pool is surrounded by a paved area, inviting guests to unwind.

4.93 out of 5 average rating, 295 reviews

POOL+Walk to Concerts + 5 mins to Historic & Beach

NEW HEATED POOL! Clean, bright, modern island home with a wonderful POOL + Dog Friendly + Perfect location! INSIDE: Updated, stylish 3BR/2BA. Professional interior design w/ everything you need for a great stay. OUTSIDE: Backyard oasis WITH POOL (amazing outdoor shower/spa, fire pit, lights, grill, & big fenced yard)!!

The A-frame home features a striking triangular design, characterized by large glass windows that invite natural light. A well-maintained lawn surrounds the property, and a spacious stone pathway leads to the entrance. Lush greenery and trees provide a sense of privacy.