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Apartment holiday rentals in Anastasia Island

Find and book unique apartments on Airbnb

Top-rated apartment rentals in Anastasia Island

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Guest favourite
Flat in St. Augustine Beach
4.92 out of 5 average rating, 201 reviews

Beachfront St. Augustine Condo • Pool, Ocean Views

Welcome to Turtle Trace, your beachfront getaway on Anastasia Island in beautiful St. Augustine! This condo offers direct pool & beach access, sweeping ocean views, and just minutes from Historic Downtown. Perfect for families, couples, or anyone wanting the ultimate coastal escape. Why You’ll Love It 🏖 Steps to the beach & pool right outside your patio door 🌅 Enjoy amazing sunrise views over the Atlantic 🏡 Gated, beautifully maintained community 🍴 Walk to restaurants, cafes & grocery stores

Guest favourite
A small dining area features a round wooden table surrounded by two wooden chairs. A bottle of wine and a decorative plant sit on the table. Natural light filters through sheer curtains, illuminating the space, while a coffee table with a tray and candles is positioned nearby.
Flat in St. Augustine
4.88 out of 5 average rating, 435 reviews

St. Augustine Studio Oasis In The Middle Of It All

A unique and charming studio apartment literally in the middle of it all. 2 block walk to Conch House. 10 minute walk over the bridge to downtown. 10 minute walk to lighthouse and Salt Run boatramp. 15 minute walk to amphitheater. Old Coast Ales Brewery, Osprey Tacos, and Odd Birds Restaurant (along with others) are each a block away. Bikes and 2 paddleboards are available and included with rental (waiver of liability required). Please message prior to arrival if you will be interested in using.

Top guest favourite
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.
Flat in St. Augustine
4.98 out of 5 average rating, 126 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.

Top guest favourite
An open dining area is situated adjacent to large windows, offering a view of a vibrant sunset over the ocean. A wooden table with several chairs dominates the space, complemented by a cozy sofa nearby. Decorative elements include a wall hanging and a potted plant.
Flat in St. Augustine Beach
4.97 out of 5 average rating, 112 reviews

Surfside Six, Direct Ocean Front, Ampitheatre

BEST spot to watch the sunrise, (and moonrise) on St Augustine Beach from every room in the condo and from the two direct beach front balconies! CORNER UNIT! TOP FLOOR! One balcony off the upstairs corner primary bedroom suite, walk in closet and ocean view King size beds in each bedroom. Anytime is a good time to be on the beach in St. Augustine! Winter Spring, Summer, or Fall! Besides being steps from the beach there are plenty of local eateries,great food, live music within walking distance.

Guest favourite
A modern kitchen space is presented, featuring open shelves displaying dishware and decorative items. A countertop includes essential cooking tools and a sink, with a sleek black faucet. A compact microwave and a stand mixer are visible, providing convenience for meal preparation.
Flat in St. Augustine
4.9 out of 5 average rating, 126 reviews

1st Floor Studio near Beach!

Easy Peasy Accommodations. Perfect for a couple or solo traveler. 1st floor studio apartment with everything you need. 2 Blocks from beach access. Easy to find right on A1A. Please note: A1A is a moderately busy two-lane roadway which you can hear the cars go by. Property is a Triplex with the two other units also being rented as Airbnbs. This listing is for the first floor and you may hear movement related noise of upstairs neighbors. Access and parking is separate from other units.

Top guest favourite
The living area features a comfortable gray sofa and armchairs, arranged around a coffee table on a patterned rug. A television is placed on a wooden media console, while natural light enters through a window, complemented by blinds and soft drapes.
Flat in St. Augustine
4.91 out of 5 average rating, 568 reviews

2 Blocks Walk to the Beach! Location, Location!

Location, location, location! Come spend days at the beach and evenings exploring the historic downtown! This apt is a 2 block walk to the beach with 2 bedrooms- 1 king and 2 twins, 1 bath, open kitchen, dining & living room, spacious deck, beachy backyard, private outdoor shower, 2 parking spaces, wi-fi, and easy access to all St. Augustine has to offer. Beach chairs, towels and an umbrella are also included. Hosted by a local family who puts lots of love into their first home.

Guest favourite
A bright and airy living area is depicted, featuring a round dining table surrounded by four white chairs. A sectional sofa with light grey upholstery is positioned nearby, complemented by decorative pillows. A well-equipped kitchen area is visible, with modern appliances and cabinetry, providing a functional space.
Flat in St. Augustine
4.92 out of 5 average rating, 208 reviews

Beach Life in Oceanview Condo

The balcony faces one of Florida's most beautiful beaches - Crescent Beach. Just 3 minutes walk from the beach, enjoy incredible sunrises and sunsets every day, heated pool, outdoor barbecue, free parking available. 15 minutes from downtown St. Augustine, surrounded by all the amenities, start your holiday on this beautiful, ancient beach. We offer short term and long term rentals hoping to provide you and your family with a relaxing, comfortable and quiet holiday resort.

Top guest favourite
The open living area features wooden floors and natural light from multiple windows. A compact dining table with folding chairs is set next to a breakfast bar. The kitchen is partially visible in the background, showcasing cabinetry and accessories.
Flat in St. Augustine
4.93 out of 5 average rating, 407 reviews

Charming "Treehouse" apartment

Let this unique 1 bdrm/1 bath (w/ claw-footed tub) apartment provide the relaxation and comfort you should expect when on vacation. The bedroom has a comfy queen-sized mattress and the black recliner in the living room has the potential to lull you into a dreamy state when you're not out exploring! The treehouse is close enough to attractions/beach/restaurants to walk or ride bikes (We have an assortment of bikes and beach paraphernalia for your use). Three day minimum.

Guest favourite
Flat in St. Augustine
4.92 out of 5 average rating, 123 reviews

Cozy Garden - Sleeps 4- hottub/outdoor shower!

This is a lovely vacation home in downtown  St. Augustine. This charming retreat offers a perfect blend of modern amenities and charm, while providing an unforgettable getaway experience. This two-bedroom, one-bath home is designed for comfort and tranquility. The main bedroom features large French doors that open onto a private deck with modern decor, while the second bedroom also offers access to the private deck with a hot tub, creating an equally inviting space.

Top guest favourite
A bright bedroom featuring a spacious bed with a gray quilt. A large window with dark curtains allows natural light to enter, illuminating the room's turquoise wall. A dresser is visible, and a doorway leads to a kitchen area in the background.
Flat in St. Augustine
4.97 out of 5 average rating, 355 reviews

Home away from Home close to everything!

An ideal place to stay while visiting our lovely historic St. Augustine. It's in a quiet neighborhood close to beaches, historic district, restaurants and stores. The unit is above the two-car garage where you enter to go up stairs to the 500 square foot apartment. It has a living room, full kitchen, bedroom and bathroom. It's a few short blocks to Intracoastal Waterway (ICW) where you can enjoy breath-taking walks. Short drive to everything!

Guest favourite
Flat in St. Augustine
4.89 out of 5 average rating, 110 reviews

Historic House of Love

Step back in time at Historic Casa De Amor, a charming apartment nestled in the heart of St. Augustine, Florida. This beautifully appointed two-bedroom apartment offers a perfect blend of historic charm and modern comfort. Enjoy amenities like a fully equipped kitchen, relaxing patio, and convenient access to the beach. Explore nearby attractions, from historical sites to vibrant downtown, and create unforgettable memories in this ideal getaway.

Top guest favourite
A living area is presented with refinished hardwood floors and neutral grey walls. A blue upholstered sofa faces a mounted flat-screen television above a white fireplace. Natural light enters through large windows, and a small potted plant adds a touch of green to the space.
Flat in St. Augustine
4.96 out of 5 average rating, 417 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.

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