Holiday rentals with beach access in Anastasia Island

Uncle Reggie's Beach House

🏝️ Welcome 2026 Spring & Summer guests to your PRIVATE beach house! Walk to the beach, restaurants, arcade, coffee & yoga. 10min drive to historic downtown St. Augustine. Fenced yard, covered deck, grill, fire pit+ luxe outdoor shower. 3 bed/2 bath, sleeps 6. Kid/pet friendly. Modern kitchen. Remote workspace. 65" TV. ORIGINAL NINTENDO & 650+ games. 2 bikes, 2 chairs, + beach cart. Free coffee. Peaceful & quiet street yet close to everything. Always 5-star service hosted by hospitality pros! ✨

Entire House w/ Backyard Hideaway - WALK TO BEACH

PARADISE ON PALMETTO: 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 and river. This bright, newly updated cottage is two blocks from the ocean and a 15 minute drive to the 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.

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.

Treehouse Artist Haven Direct Oceanfront 2br

Located along a stretch of pristine beach is this spectacular house with a beachfront location like no other. This unique home encompasses 3 separate floors. This is the middle of the 3 floors “The Artists Haven”. Inside you will find 2 bedrooms, a bath and an open plan living/dining area that opens out to a surrounding deck with seating. Enjoy uninterrupted ocean views from the wrap around deck with many places to relax & watch dolphins, sip your morning coffee or watch the pink sunsets. 1002

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.

Walk Historic Downtown! “Blue Heaven”

Stunningly renovated cottage combines modern amenities with vintage charm... * 2 master suites with queen beds * Quiet neighborhood walking distance to explore The Nation's Oldest City * Clawfoot tubs inside and out (along with showers, of course!) * Big screened-in porch with hanging daybed * Off-street paved parking * Fully fenced backyard, Weber grill, gas fire pit * Fast Wi-Fi and Smart TV * 2 blocks to Fish Camp, Ice Plant, LaNuvelle, trolley stop * 10 minute walk to central downtown

NEW Island bungalow - Cozy & Classy

Perfect cozy bungalow for a stay in the nations oldest city. Huge bedroom with a new king bed. Living room with a sleeper sofa and TV. Coffee station, french press, microwave, and mini fridge. Full of artwork. Paintings and a sculpture. Huge stone tiled shower. Located off Anastasia Blvd with great restaurants, coffee shop, pubs and fun for the kids! Located 1 mile the the Anastasia beach state park and then a little over a mile to the beach!! Does not have a kitchen. Walk to Alligator Farm!

Luxury Modern Home in Prime Location 2BDR-3BTH

Book your Spring Break vacation with us! Our contemporary home offers comfort, elegance, and curated amenities. Explore the historic downtown, climb the lighthouse, enjoy live performances, indulge in local cuisine, and relax on the nearby beach. The Lighthouse Beacon is the perfect retreat for families and friends, catering to all preferences. Experience the magic of Saint Augustine and create cherished memories. Book your stay now and let us be your guiding light in this captivating city.

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.

St Augustine Beachside Home - Walk to Beach

Time to Relax at our St Augustine canal front getaway! Great family destination just 15 min. to Historic Downtown St Augustine. Neighborhood features PRIVATE Beach Access with a less than 10 minute . walk, depending on pace, to the Beach. Boating and Fishing at your Fingertips with private, over-the-water dock and ramp to floating dock where you can tie up your own boat/kayak/jet skis. The perfect end to your beachside dream day will be watching the sunset while on your private dock.

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.

Beach and Serenity

6 BLOCKS to BEACH, off of the intercostal! Studio apartment, sleeps up to 4. Quiet neighborhood, close to all. Several restaurants/shops within walking distance. Beach bikes included, perfect for bike rides along the beach. Private entrance off of porch, which includes chairs to relax in, beach toys, towels, chairs. *yes, we are pet friendly, however, ONE PET PER STAY WITH APPROVAL *also, we cannot split weekends, so please book accordingly, fridays and Saturdays booked together