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Vacation rentals in Anastasia Island

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Anastasia Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

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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 St. Augustine
4.93 out of 5 average rating, 330 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 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.
Home in St. Augustine
4.94 out of 5 average rating, 130 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

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 St. Augustine
4.99 out of 5 average rating, 200 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.

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, 148 reviews

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

This hidden gem (Unit B) is a 2 BR/2 bath home that is part of a duplex within a few minutes walk of some of the best St. Augustine has to offer and a short drive to St. Augustine Beach. The layout is perfect for a family/friends getaway, with the downstairs being comprised of 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.

Guest favorite
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.
Home in St. Augustine
4.94 out of 5 average rating, 223 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.

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 St. Augustine
5 out of 5 average rating, 363 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

Guest favorite
The exterior of the two-story turquoise house is showcased, featuring a deck with seating and a beautifully landscaped yard filled with greenery and tropical plants. A clear blue sky enhances the inviting appearance of the home, which is situated in a residential area.
Apartment in St. Augustine
4.88 out of 5 average rating, 104 reviews

Ocean Views, Beach Bikes, Sunny Deck, Steps 2 Sand

Save my home to your wish-list by clicking on the <3 in the upper right corner! >Beach access across the street (1 min walk)! >Entire upstairs apartment >Gorgeous ocean views! >2 beach bikes provided >Private patio with seating >Sleeps 3 (2 in master, 1 on daybed) >Downtown St. Augustine is a 17 minute drive >Close to A1A Back 40 Beachside >Drip coffee pot >Electric Grill >Washer + Dryer access >Smart TVs with Netflix, Hulu, etc. >2-3 days of supplies provided (TP, trash bags, pods, etc.)

Guest favorite
Guest suite in St. Augustine
4.95 out of 5 average rating, 786 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.

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, 518 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.

Guest favorite
Cottage in St. Augustine
4.82 out of 5 average rating, 387 reviews

Sea La Vie Beach Studio.

Our renovated studio is on a quiet cul-de-sac, one block from the beach! It is one side of a duplex and is perfectly located within walking distance to restaurants, family-friendly activities, nightlife, and public transport. It is across the street from the pier and the piers weekly farmers market. It is a short drive to historic downtown St Augustine. The neighborhood is quiet and safe. Our place is good for couples, solo adventurers and business travelers.

Guest favorite
Vacation home in St. Augustine
4.91 out of 5 average rating, 104 reviews

*The Lookout* Downtown SA retreat, Free Bikes/WIFI

-1 bedroom private apartment in the trees -Located in Lincolnville and close to downtown -Tucked away from the noise of downtown -Walk to Historic Downtown, St. Augustine Fish Camp, Blue Hen, and Flagler College -Great retreat for couples -Fast wifi and Keurig coffee -Clean, comfortable, and safe -10-15 min drive to the beach Need more space? Add on “Deja Blue” a studio located directly below "The Look Out".

Top guest favorite
A bright living area features a cozy blue couch and a modern coffee table centered on a plush rug. A stylish chandelier hangs above, complementing the elegant fireplace. Sunlight streams through large windows, illuminating the space adorned with light grey walls and greenery.
Apartment in St. Augustine
4.93 out of 5 average rating, 380 reviews

Anastasia Grand # 1-Between Downtown and the Beach

Located on beautiful Anastasia Island, this 1920's fully renovated luxury apartment is walking distance to historic St Augustine via the Bridge of Lions and biking distance to St Augustine Beach. In the early Florida boom period of the 1920's, British developer D.P. Davis fell in love with St. Augustine and designed the Davis Shores neighborhood right over the Bridge of Lyons on Anastasia Island.

Popular amenities for Anastasia Island vacation rentals

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