Vacation rentals in Anastasia Island

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Top-rated vacation rentals in Anastasia Island

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Top guest favorite
A spacious bedroom features a comfortable bed with a woven headboard, flanked by two bedside lamps. Natural light enters through a window dressed with wooden blinds. A ceiling fan circulates air, while decorative paddles add an interesting touch to the wall.
Apartment in Butler Beach
4.93 out of 5 average rating, 336 reviews

Toast Sunsets from the Wraparound Deck at a Coastal Oasis

A wonderful getaway, this property includes two airbnbs. A two story home with a detached guesthouse. These listings can be rented separately or together, if available. This listing is space is about 1,000 sq ft. You will have exclusive access to the second story apartment and wrap around porch. You will have one dedicated parking spot. There is a small backyard area with an outdoor shower that is shared with the other Airbnb. Access to the apartment is via keypad code. Were available if you need anything, but many times we only communicate with our guests through Airbnb! This Crescent Beach retreat is set back a bit from the road just 3 blocks from the ocean and 8 miles from downtown. Uber is the best way to get around without a vehicle. The Crescent Beach house is on A1A, set back a bit from the road. A1A is a moderatly busy two lane highway. However, you access the home from the backyard, which is also where you park, via a short grass road. Uber is the best way to get around if you do not have your own vehicle. This property includes two airbnbs. Each listing has one dedicated parking space in the rear of the property via a short grass backroad. The parking spaces are right next to each other.

Top guest favorite
A spacious living area features wood-paneled walls and large glass doors, offering views of the ocean. A chandelier hangs from the ceiling. The seating area includes a comfortable couch and a dark coffee table, while a television with vibrant display adds a touch of modernity.
Condo in St. Augustine
4.92 out of 5 average rating, 118 reviews

Treehouse Artist Haven Direct Oceanfront 2br

Located along a stretch of pristine beach is this spectacular house with a beachfront location like no other. This unique home encompasses 3 separate floors. This is the middle of the 3 floors “The Artists Haven”. Inside you will find 2 bedrooms, a bath and an open plan living/dining area that opens out to a surrounding deck with seating. Enjoy uninterrupted ocean views from the wrap around deck with many places to relax & watch dolphins, sip your morning coffee or watch the pink sunsets. 1002

Top guest favorite
A panoramic view of a beach scene at sunset, featuring vibrant clouds in shades of pink, orange, and purple. The sun dips below the horizon, reflecting off the water's surface. Grassy dunes are visible in the foreground, framing the tranquil scene.
Guest suite in Butler Beach
5.0 out of 5 average rating, 376 reviews

Entire guest suite short walk to beach.

Enjoy exploring beautiful, historical St. Augustine then kick back and take it easy at this private, quiet beach retreat within a short walk to the beach. Separate keyless entry allows for self check-in. Queen size bed, fully furnished, with amenities including a Keurig coffee maker, iron, hair dryer, beach cruiser bicycles, beach chairs, towels, umbrella and gas grill for cooking out. Flat screen TVs in both the living room and bedroom with Netflix and Amazon Prime included and Free WiFi

Top guest favorite
Bungalow in Butler Beach
4.96 out of 5 average rating, 238 reviews

Ooo Laa Laaah Pets welcome

Private, fenced in yard and private Free standing cottage in quiet neighborhood. Private, fenced in yard! Pets are welcome. Fees apply. 2 washers and dryers, internet/wifi, 2 smart TVs. All kitchen appliances. One story. The beach is a one block stroll with no major streets to cross. Keep your car at home..walk to the beach 2 minutes stroll . Downtown, St. Aug. is a 10 minute car ride. Not a condo scene. Crescent Moon cottage is in front but completely separate. Shared laundry room.

Top guest favorite
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 Beach
5.0 out of 5 average rating, 129 reviews

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

Top guest favorite
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.
Condo in Butler Beach
4.99 out of 5 average rating, 210 reviews

SeaPlace Ocean & Pool Views, 2/3 Steps to Beach

Beautiful St. Augustine Beach ocean & pool views from this 2/2.5 townhouse style condo steps to the beach. Come enjoy everything this vibrant city has to offer. Two quiet bedrooms and bathrooms upstairs. 2 private balconies. Downstairs is a full kitchen, dining area for 6, half bathroom, living area w/ newer 65" TV. 10 minutes from historic downtown. Family friendly resort community w/ pools, tennis, pickleball, basketball and bocce’ ball courts. Book now and let the island magic begin.

Top guest favorite
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.
Home in St. Augustine
4.89 out of 5 average rating, 113 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

Top guest favorite
A modern kitchen is featured, showcasing sleek white cabinetry and a large island with seating for three. A stainless steel stove and hood are positioned centrally, complemented by minimalist decor. Natural light fills the space through a nearby glass door and staircase leading to the upper level.
Apartment in St. Augustine
4.99 out of 5 average rating, 164 reviews

2BR/2B Get Away-Walk to St. Aug

This gem (Unit B) is a 2 BR/2 bath home that is part of a duplex within a few min. walk of some of the best St. Augustine has to offer and a short drive to St. Augustine Beach/amphitheater. The layout is perfect for a family/friends getaway, with the downstairs including the living area, kitchen, 1 BR, and 1 bath, and 1 additional BR and bath upstairs. 5-min bike ride to the beach, 5-min walk to all the bars and restaurants on Anastasia Blvd, and a 10-min walk(.6mi)to downtown St. Aug.

Top guest favorite
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.
Guest suite in St. Augustine
4.99 out of 5 average rating, 537 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.

Superhost
A newly renovated historic home is set against a serene natural backdrop, featuring a large deck accessible via a wooden walkway. The exterior showcases multiple arched windows and a modern roof deck, surrounded by lush vegetation and reflected in the calm waters of the marsh.
Cottage in Vilano Beach
4.9 out of 5 average rating, 178 reviews

The Shire on 1 acre marshfront with dock and Spa

One of a kind 1930s historic home, newly renovated and transformed into a beautiful secluded getaway. new luxury finishes, while holding its traditional charm. No Events allowed. Rooftop deck, sunrise views of the Atlantic ocean, Downtown, and sunsets over the river. The new dock with covered roof hosts a national geographic like eco system. It’s short walk to the beach and 3 miles to downtown St George street. Follow along @carcabaroad for weekly content of the home.

Top guest favorite
A living room is highlighted by a modern fireplace beneath a flat-screen television. Natural light floods the space through multi-paned windows, complementing elegant gray walls. A comfortable blue sofa is paired with a circular coffee table, while a potted plant adds a touch of greenery.
Apartment in St. Augustine
4.94 out of 5 average rating, 326 reviews

Short Scenic walk into Historic St Augustine

Stay in Style on Anastasia Island Step into timeless elegance at this fully renovated 1920s apartment. Nestled in the heart of historic Davis Shores, this beautiful retreat blends old Florida charm with modern comfort. 🌴 Perfect Location Walk across the Bridge of Lions to the cobblestone streets, shops, and restaurants of historic St. Augustine. Surrounded by local cafés, parks, and coastal scenery.

Top guest favorite
Bungalow in St. Augustine
4.96 out of 5 average rating, 127 reviews

1928 Coastal Bungalow w/ 2 King Beds | Walk to Amp

Welcome to Salt Run Stay — a lovingly restored 1928 beachy bungalow in the heart of St. Augustine. Ideal for couples, friends, families and solo travelers, the bungalow is walking distance to the famous Lighthouse, Salt Run Inlet, a boat launch, restaurants, cafes and the Alligator Farm. You can also easily bike to the Amphitheater, Anastasia State Park and beach, and the historic downtown area.

Popular amenities for Anastasia Island vacation rentals

Frequently Asked Questions

  • Where is Anastasia Island located?

    Anastasia Island is just off the northeast coast of Florida, near the city of St. Augustine. It is known for its beaches, natural preserves, and relaxed coastal atmosphere.

  • When is the best time to visit Anastasia Island?

    Late spring and early fall are often suggested for comfortable weather, with temperatures ranging from about 65 to 84°F (18 to 29°C) and manageable rainfall. Cooler winters appeal to those wanting fewer crowds, while summer brings warmer days and higher humidity.

  • What are some things to do near Anastasia Island?

    Explore wide sandy beaches, visit Anastasia State Park for walking trails and native wildlife, or discover the historic St. Augustine Lighthouse and Maritime Museum. The area also has local seafood restaurants, nature preserves, and opportunities for water activities.

  • How is the weather near Anastasia Island?

    Anastasia Island experiences mild winters around 45–68°F (7–20°C), with warmer, humid summers near 90°F (32°C) and peak rainfall during late summer. Spring and fall are frequently noted for moderate temperatures and less humidity, making outdoor activities inviting.

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