House holiday rentals 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.

La Rêverie | Downtown Boutique, Historical Chic

Step inside La Rêverie, a distinguished 19th-century residence steeped in American heritage, meticulously restored & reimagined for today's discerning traveler. Centrally located on original coquina pillars, La Rêverie boasts cathedral ceilings suffused with sunlight and a bespoke French kitchen with chef-grade amenities. Invite guests to the sitting room, carefully designed to foster camaraderie. Choose from three plush bedrooms, each with an en-suite bath for a luxurious, yet private retreat.

HGTV DesignerHome•HeatedPool•Walk/Bike 2 Downtown

Off Street Parking 3 Min Drive/ 15 Min Walk to Historic Downtown 2 Min Drive to the St Augustine Amphitheater 2 Min Drive to Anastasia State Park Beach 1 Min Drive to Anastasia Fitness Club/Suana-Steam Rm/Pool Looking to get away from the hustle & bustle of the city? This designer home with an amazing pool is the perfect place to recharge. Downtown & the scenic beaches in Anastasia State Park are just a minutes away. With spacious living & modern amenities, the Home offers maximum comfort

Beach Getaway - Upstairs

Welcome! In our cozy home, you will not only feel the comfort of home but you’ll also be centrally located in the heart of our beach town with restaurants & shops within walking distance. Our home is less than a 5min walk to the beach & only a 10min drive to St. Augustine's historic downtown with so much to explore. This upstairs unit of this 2-story duplex has 2 bedrooms, one bathroom with a bath, comfortable living/dining area and a kitchen - ideal for a family or a small group of friends.

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.

Cozy Clean Comfortable Beach Home

This is a beautiful clean and cozy home is a hidden gem.. Located in on the beachside of A1A, and just a quick drive to downtown St. Augustine! Perfect for a family beach vacation! 2 bedrooms, 1 King bed and 1 Queen bed, 1 full bathroom, and a private outdoor shower! The kitchen is completely stocked with everything you need to cook. Washer and Dryer on site. The back porch area receives morning sun, and the front door faces sunset. Polished concrete floors, Pets are welcome friends!

New Build•Walk to the Beach•Bikes•Beach Toys

Welcome to our beach home on Anastasia Island. It is located directly on the east side of the famous and historical A1A, the road that will take you to everything St. Augustine has to offer! Built in 2020, and is equipped with dual pane impact windows and amenities of a new contemporary build. From our front doorstep you can walk to the beach in minutes (0.39 mile). You can enjoy magical sunrises over the ocean and beautiful sunsets over the river. We have bikes and beach gear awaiting you.

The Beach House at Crescent Beach

The Beach House located at Crescent beach. Across the street from the beach with easy access and two blocks from the intracoastal. Drive 15 to 25 minutes to St. Augustine, depending on traffic, our nations oldest city with shopping and many historic sites. Excellent restaurants within minutes of house Pets (2 small or 1 large) must be mature and house trained. Please provide pet information at time of booking and pet fee must be paid. Great for boaters Car Limit: 2 Guest Limit: 6

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.

St. Augustine beach house

.House is located just south of historical downtown St. Augustine, by beautiful Crescent and historical Butler beaches. Situated within a short drive from downtown and a few minutes walk to the beach. Perfect for those who enjoy exploring, shopping and the beach. Completely renovated 3 bedroom 2 bath house with large yard and plenty parking. Large covered backyard deck for out door lounging, dining. The front yard features an authentic native Indian Tiki hut with comfortable seating.

St Augustine Entire Home, King Bed, Pet Friendly

Casita Luxe Retreat Near Historic St. Augustine – Pet-Friendly Haven! Discover this luxurious 3-bedroom, 2-bath retreat! Designed with a modern luxe aesthetic, it features custom wood paneling, a fully equipped kitchen with a chic island, and a king-size plush mattress. Enjoy the large, fenced yard, fire pit, outdoor shower, and fun family games. Pet-friendly, with Wi-Fi, smart TVs, and parking included this home offers comfort and style in an up-and-coming neighborhood. Book now!