Apartment holiday rentals in Anastasia Island

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Top-rated apartment rentals in Anastasia Island

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Top guest favourite
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.
Flat in St. Augustine
4.93 out of 5 average rating, 315 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.

Guest favourite
Flat in St. Augustine Beach
4.93 out of 5 average rating, 199 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

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, 117 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, 108 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.

Top guest favourite
Flat in St. Augustine
4.93 out of 5 average rating, 684 reviews

2 Blocks Walk to the Beach! Renovated Beach Apt

Location, location, location! Bright 2nd floor beach apt, recently renovated, 2 blocks to the beautiful sands of St. Augustine Beach! Spend your days at the beach and evenings exploring the historic downtown. The apartment has 2 bedrooms- 1 king and 2 twins, new bath, kitchen, dinning and living room with an open floor plan, balcony deck, outdoor shower, parking, Roku TV, & wi-fi. Listen to the waves from the deck at night! Hosted by a local family who puts lots of love into their first home.

Top guest favourite
An aerial view captures the colorful buildings and lush landscaping of the property, with the iconic Bridge of Lions visible across the water. Boats can be seen docked along the Intracoastal, while the vibrant greenery frames the scene, creating a serene setting.
Flat in St. Augustine
4.94 out of 5 average rating, 108 reviews

LIONS VIEW | Waterfront | 5-min walk to Downtown

Welcome to our stunning 3BR/2.5BA 2nd floor unit, boasting the most magnificent views of Downtown St. Augustine. Perched on the east side of the iconic Bridge of Lions, our home offers a unique vantage point of the Intracoastal, creating an unforgettable backdrop for your vacation. Location is key, and our place puts you in the heart of the action. Effortlessly explore the historic charm of Downtown St. Augustine on foot, with just a short 5-minute walk across the bridge. 10-mins from beach.

Top guest favourite
A shaded outdoor area features a hammock with striped fabric, inviting relaxation. Stone pavers lead to a landscaped garden area with green foliage and seating. A patio setting is visible in the background, complete with table and chairs for outdoor dining.
Flat in St. Augustine Beach
4.88 out of 5 average rating, 283 reviews

Low Tide - Beach Bungalow

LowTide part of Sage Tides Triplex - East of A1A beach Blvd , ground floor, old-Florida (build in 1923!) pet-friendly 2 bedroom, cozy unit (900 sf) with a private yard & patio/garden living space & two hammocks. Located on a dead-end street easy walk (2 houses away) to the beach. Yes, old Tile floors, some with cracks but cool for your feet or pets & easy to sweep. Sleeps 2 comfortably, 3-4 tight . There is one full bath (shower only) new in 2022 and the kitchen is fully equipped.

Top guest favourite
A spacious living area features a comfortable sofa and a patterned area rug, with a wall-mounted television visible. Large windows provide natural light, and a decorative console table stands against the wall. Artwork adorns the walls, enhancing the inviting ambiance.
Flat in St. Augustine
4.99 out of 5 average rating, 147 reviews

A1A Beach Retreat Unit E - Clean Full Apartment

Discover the perfect St. Augustine Beach getaway! This 2-bedroom (queen beds), 1-bath vacation rental is in the heart of St. Augustine Beach, just a short stroll to local favorite restaurants, lively watering holes, and the beach. Only 5 miles from historic downtown, it’s easy to explore the area’s rich history and charm. Enjoy the convenience of 2 reserved compact parking spaces, making your beach days a breeze. More than a stay—it’s a lifestyle. Book now and start making memories!

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
A spacious bedroom showcases a king-size bed with decorative pillows and a tufted headboard. Natural light streams in from adjacent doorways, highlighting wooden flooring. Two bedside lamps provide soft illumination, while a ceiling fan with leaf-shaped blades adds a touch of charm.
Flat in St. Augustine
4.93 out of 5 average rating, 241 reviews

Elegant, FREE BIKES dog-friendly downtown apart.

This huge pet-friendly apartment in a beautiful historic house is located only two blocks from the heart of the Old Town and is sanitized between all guests . You will love the first floor spacious bedroom with a very comfortable king-size bed, sofa, and access to the back yard, as well as the large and elegant living room and a full kitchen. Borrow our bikes to roam around town. There is one guaranteed parking space. Pet fee is $40 per dog per stay (max of 2 dogs).

Superhost
A modern dining area features a round wooden table surrounded by four upholstered chairs, offering comfort during meals. Large windows allow natural light to fill the space, showcasing views of greenery outside. A minimalist wall art piece enhances the stylish and welcoming atmosphere.
Flat in St. Augustine
4.91 out of 5 average rating, 114 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, 354 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!

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