House vacation rentals in Anastasia Island

The exterior of the cottage is showcased, featuring a bright blue metal roof, white brick walls, and charming blue shutters. A patio with outdoor seating is visible, surrounded by lush greenery and palm trees under a colorful sunset sky.

4.98 out of 5 average rating, 289 reviews

Entire House w/ Backyard Hideaway - WALK TO BEACH

PARADISE ON PALMETTO: 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 and river. This bright, newly updated cottage is two blocks from the ocean and a 15 minute drive to the 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.

The sitting room features a blend of warm green and golden hues. A brown leather sofa is adorned with colorful pillows, complemented by a green accent chair. Sunlight filters through the white window blinds, illuminating a vibrant area rug and a piece of art depicting a pelican.

5 out of 5 average rating, 122 reviews

La Rêverie | Downtown Boutique, Historical Chic

Step inside La Rêverie, a distinguished 19th-century residence steeped in American heritage, meticulously restored & reimagined for today's discerning traveler. Centrally located on original coquina pillars, La Rêverie boasts cathedral ceilings suffused with sunlight and a bespoke French kitchen with chef-grade amenities. Invite guests to the sitting room, carefully designed to foster camaraderie. Choose from three plush bedrooms, each with an en-suite bath for a luxurious, yet private retreat.

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, 216 reviews

Downtown HistoricLuxury • Designer Kitchen & 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 spacious bedroom features a light-colored wooden floor and a ceiling fan overhead. A decorative desk and chair are positioned against the wall, accompanied by a wall-mounted mirror and potted plants. Colorful artwork, including a cow painting, enhances the inviting atmosphere.

4.91 out of 5 average rating, 341 reviews

NEW Island bungalow - Cozy & Classy

Perfect cozy bungalow for a stay in the nations oldest city. Huge bedroom with a new king bed. Living room with a sleeper sofa and TV. Coffee station, french press, microwave, and mini fridge. Full of artwork. Paintings and a sculpture. Huge stone tiled shower. Located off Anastasia Blvd with great restaurants, coffee shop, pubs and fun for the kids! Located 1 mile the the Anastasia beach state park and then a little over a mile to the beach!! Does not have a kitchen. Walk to Alligator Farm!

The two-story beach house is framed by a lush green lawn and palm trees, featuring a spacious front porch with white chairs. Large windows and a gabled roof enhance the inviting appearance. A clear blue sky serves as the backdrop.

4.89 out of 5 average rating, 163 reviews

Beach & Serenity; The Perfect Location in St. Aug

Forget your worries in this spacious and serene space. Beautiful beach house 6 blocks to beach, 2 blocks to intercoastal Drive on to the beach at one end of the street, Easy walk to the best sunsets at the marsh Restaurants at each end of the street Upstairs and downstairs screened porches *PLEASE NOTE, AND THIS IS IMPORTNAT * We cannot split weekends. Friday and Saturday nights booked together *ONE PET PER STAY W/ APPROVAL *no washer/dryer available, hang dry only *STRICT CHECK IN/OUT TIMES

A modern living area is shown, featuring a comfortable blue sofa and a light gray rug. A wooden table with black chairs is visible in the foreground. The kitchen area includes dark cabinetry and stainless steel appliances, while a wall-mounted television adds to the space's functionality.

4.99 out of 5 average rating, 116 reviews

Beach Getaway - Upstairs

Welcome! In our cozy home, you will not only feel the comfort of home but you’ll also be centrally located in the heart of our beach town with restaurants & shops within walking distance. Our home is less than a 5min walk to the beach & only a 10min drive to St. Augustine's historic downtown with so much to explore. This upstairs unit of this 2-story duplex has 2 bedrooms, one bathroom with a bath, comfortable living/dining area and a kitchen - ideal for a family or a small group of friends.

A light-filled living area features a modern TV console with a large screen and decorative accents. The space includes a comfortable sofa, two armchairs, and a dining area with a table and chairs, seamlessly connecting to the fully equipped kitchen.

4.94 out of 5 average rating, 125 reviews

Sunshine by historic downtown & the beach

Welcome to Casa Sunshine! A charming home with 2 beds, 2 baths just by historic downtown and near stunning beaches. Fully stocked for cooking, sleeping, laundry & kids' fun. Enjoy beach gear and games, board and mini arcade games for those chill days. Explore historic landmarks, dining, & nightlife, all within walking distance. Unwind in the spacious comfy bedrooms with ample sleeping. Ideal for families or small groups. You'll for sure have an enjoyable and memorable stay in St. Augustine!

A single-story house is presented with a light exterior and a sloped roof. The front porch is accessible by three steps, and large windows allow ample natural light to fill the interior. Lush green grass and a few flower bushes enhance the front yard.

4.87 out of 5 average rating, 146 reviews

The Beach House at Crescent Beach

The Beach House located at Crescent beach. Across the street from the beach with easy access and two blocks from the intracoastal. Drive 15 to 25 minutes to St. Augustine, depending on traffic, our nations oldest city with shopping and many historic sites. Excellent restaurants within minutes of house Pets (2 small or 1 large) must be mature and house trained. Please provide pet information at time of booking and pet fee must be paid. Great for boaters Car Limit: 2 Guest Limit: 6

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.

4.97 out of 5 average rating, 289 reviews

St Augustine Beachside Home - Walk to Beach

Time to 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 a less than 10 minute . walk, depending on pace, 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.

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.

4.96 out of 5 average rating, 100 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 tranquil backyard area is featured, showcasing a heated pool surrounded by lush greenery. Two black chairs are positioned on the stone patio, offering a comfortable spot for relaxation. The space is enclosed by vibrant tropical plants, enhancing the private atmosphere.

4.96 out of 5 average rating, 178 reviews

Pool home oasis steps to ocean

Cottage style home with comfortable porches to enjoy sound of ocean waves breaking on the front and back porches. Pool in the back yard (heated by request for $50 per day) cookshed, fenced with lush trees and woods to the east. The inside looks large with high wood ceilings and multiple windows and glass doors to the beautiful pool area. Located on a dead end street in a family neighborhood with 5 star restaurants nearby. Fifteen minute drive to downtown St. Augustine.

The kitchen area features wooden cabinetry, a stove, and a refrigerator. A ceiling fan is present above a bar counter with seating, while a dining table is positioned nearby. Natural light streams in through a window, creating a welcoming environment.