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, 305 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
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, 414 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 charming view of the Italian restaurant Pizzalley's, featuring a decorative balcony adorned with hanging plants. The building’s colorful facade complements the vibrant street lined with trees and vintage-style street lamps, creating a lively atmosphere in the historic district.
Flat in St. Augustine
4.97 out of 5 average rating, 773 reviews

Balcony apt on USA’s oldest Street (St. George St)

"The Heart of St. Augustine" Voted #1 Airbnb in St Augustine by Trip 101, # 5 Top 10 Airbnb's in St. Augustine" by Territory Supply and in the "Top 15 Best Airbnb's in Florida" by Road Affair. Live music, scrumptious food, craft drinks, and the hustle and bustle of people walking the historic St. George St, all surround you. Relax and people watch from your balcony. Sightseeing, restaurants, trolley stop and nightlife are steps away. This apt is in the center of it all. NYE is a 3 night min

Top guest favourite
Flat in St. Augustine
4.93 out of 5 average rating, 671 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.

Guest favourite
The exterior of the mid-century bungalow is surrounded by lush landscaping and palm trees. An expansive deck is visible, offering a space for outdoor relaxation. The green yard features a variety of shrubs and plants, contributing to a serene, natural atmosphere.
Flat in St. Augustine
4.96 out of 5 average rating, 122 reviews

*1 Block From the Beach! 5 min Drive to Downtown *

In a quiet Vilano Beach community this mid-century bungalow with expansive deck is a beach lovers paradise. Just a stones throw away from one of the most beautiful and private beaches Florida has to offer, and a short drive or water taxi to historic downtown St Augustine, this is truly a gem of a location. You can walk to Publix, bars, restaurants, coffee shops, pier, water taxi, and more. This guest apartment of a 2 story duplex is on the second floor, which has a private entry and parking.

Top guest favourite
A light-filled dining area showcases a white table surrounded by four aqua-colored chairs. Large windows are draped with sheer curtains, allowing natural light to brighten the space. An accent cabinet displays decorative items, and a green plant adds a touch of nature.
Flat in St. Augustine
4.95 out of 5 average rating, 495 reviews

Vilano Beach Vagabond's House~St Augustine FL

Beach Lovers Bungalow-ocean just steps from lovingly kept apartment in a Mid Century beach house on large tropical property. Easy 1-min walk to beach path. Two blocks to Publix grocery, restaurants /cocktails. Heart of walkable beach neighborhood. Spacious, sparkling clean. Both BRs w/private bath. Comfortable layout, full kitchen. Private entrance. Short Uber ride downtown for Night of Lights visitors. Perfect for couple, 2 friends, mother/daughter trips & Flagler College parents.

Superhost
A bright and airy room is showcased, featuring a spacious queen bed and a Murphy bed for flexible use. The area includes a comfortable blue chair next to a small table, with natural light flooding in from windows and a private entrance visible.
Flat in St. Augustine
4.83 out of 5 average rating, 303 reviews

100 Steps to Beach, Deck w Ocean View, Beach Gear

Add my property to your wishlist by clicking on the <3 in the upper right corner! *Book 2 nights, get the 3rd night 30% off!* >100 steps to the beach! >Private upstairs deck for lounging + ocean views! >Dog friendly with nightly pet fee (one dog only) >Completely upgraded interior >Drip Coffee Maker >Comfy queen bed >Murphy Bed can be closed to make extra space >Dining space >Compact washer/dryer >Smart TV + Wifi >Netflix + Hulu only >Beach chairs + beach towels for two provided

Top 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
4.94 out of 5 average rating, 185 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, 402 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
An outdoor seating area features modern gray chairs arranged around a fire pit, which is surrounded by soft sand. Lush palm trees and colorful plants provide a tropical backdrop, while the building's balconies overlook the inviting courtyard, illuminated by warm lights against a vibrant sunset sky.
Flat in St. Augustine
4.97 out of 5 average rating, 103 reviews

>•< Resort Style Retreat >•<

Welcome to our cozy and stylish 1-bedroom, 1-bathroom apartment situated in the serene and picturesque coastal town of Saint Augustine Beach. This thoughtfully designed space offers a blend of comfort and relaxation—ideal for individuals or couples looking for a peaceful getaway. Nestled by the intercoastal waterway, the apartment boasts one of the most stunning views from the balcony where you can unwind and soak in the beauty of your surroundings.

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, 344 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!

Top guest favourite
The exterior of a tropical retreat is captured, showcasing a wooden deck with colorful surfboard decorations on the walls. Bright green foliage and plants frame the entrance, while sunlight creates playful shadows on the stucco surface.
Flat in St. Augustine Beach
5 out of 5 average rating, 134 reviews

Beach Break! Walk to the beach! 1BRw/Private Patio

Beach Break! Enjoy your beach vacation and all St. Augustine Beach has to offer from the perfect tropical retreat! This luxury 1 Bedroom / 1 Bath accommodation is centrally located within short walking distance to the beach, coffee shops, the taco shop, surf shops, restaurants, parks, and shopping! After your day at the beach, come back to relax in the hammock under the palms in your private tropical patio. You'll fall in love with BEACH BREAK!

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