Apartment holiday rentals in Anastasia Island

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.

Inviting 2/2 BR - Walk to Town

This St. Augustine apartment is right in the heart of quaint & historic downtown! This lower level apartment is furnished with a king bed in the master bedroom with a bath and a queen bed in the second bedroom with bath and is perfect for 1-4 guests. A short 5-8 minute walk allows visitors to explore the many downtown historic sites, museums & restaurants. One parking spot is available on site. There is free parking on our street (except from Nov15th-Jan11th during Nights of Lights).

Oceanfront Bliss: Beach Views

Welcome to your oceanfront oasis in St. Augustine Beach! Featuring a spacious king suite, a comfy queen bedroom with twin trundle, and a sleeper sofa, it offers stunning sunrise views, a modern boho surfer’s vibe, and an updated chef’s kitchen. Steps to one of the best beaches in the east coast and walk to lively local restaurants and bars, it’s minutes to St. Augustine’s Nights of Lights, Amphitheater, and more! This isn’t just a vacation rental—it’s your personal seaside escape. Book now!

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.)

Carriage Hse in the trees, Historic St. Augustine

You have found your cozy oasis tucked under tall shade trees in a private, lush tropical courtyard in the historic district. This relaxing space is walking distance to everything. It's adorned with 2 covered porches, the Courtyard porch and breakfast porch. Enjoy and relax in the courtyard lit by hundreds of tiny laser lights at night. You will likely see our tortoises roaming the completely fenced property. In warm weather enjoy the shared pool. *Guests must be quiet ish after 9:30

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.

Heart of Downtown. Studio on St. George Street

A hip modern steam punk vibe in the ancient city. This completely renovated studio is located on St. George Street, the main pedestrian area in St. Augustine. When you stay here you are in the heart of everything. Countless restaurants, bars, shops and cultural events are just steps from your door. A dedicated parking space is included. It is located an easy walk along sidewalks and pedestrian only street approximately 2 minutes from the apartment.

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!

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.

Deja Blue l Fire pit l Steps to Beach l Dogs OK

Located just steps from the beautiful sandy St. Augustine beach is this gorgeous apartment with everything you could need for a relaxing, beachside stay: ->One block to the beach! ->Cozy backyard with firepit, seating, and outdoor shower ->Stocked for the beach: Towels, chairs, umbrella, beach wagon, all supplied for your stay ->Dog friendly for up to 1 dog (see Other Things to Note section for additional details)

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.

The Turtle Nest, a delightful Oceanfront getaway

Welcome to the Turtle Nest. This Oceanfront 2 bedroom is a delightful getaway for 2 or 3 people. Come and enjoy the gorgeous sunrise and moonrise views over the ocean from this charming and newly renovated hideaway. Five minutes from the heart of historic St Augustine and with direct access over the dune to the peaceful Vilano Beach, its hard to wait to get a cool drink in hand and one's toes in the sand.