House holiday rentals in Anastasia Island

An expansive backyard features a refreshing saltwater pool and a hot tub, surrounded by lush turf landscaping. A two-story building with a wooden staircase overlooks the serene outdoor space, framed by palm trees and vibrant plants. Lounge chairs are positioned nearby for relaxation.

4.98 out of 5 average rating, 129 reviews

Driftmark Cabin - RV friendly, Pool + Beach!

Experience the ultimate beachside getaway at our fully renovated Airbnb, just steps away from the sun-kissed sands. This luxurious retreat offers modern comfort with a private pool and inviting hot tub, allowing you to unwind in style. The recently upgraded interior boasts premium amenities, ensuring a relaxing stay. Outside, lush turf landscaping surrounds the pool, creating an oasis of comfort. Whether you're lounging by the pool, or enjoying the beach a stone's throw away, Driftmark delivers.

The historic home features a grand façade with elegant columns and a decorative balcony. A wrought iron gate opens to a brick pathway leading to the entrance. Large windows allow for ample natural light, framed by soft garden landscaping against a vibrant sunset backdrop.

4.97 out of 5 average rating, 442 reviews

Genovar Mansion Rose Garden Suite Private Entrance

The direct view of a gorgeous live oak canopy on Magnoila Avenue and incredible architecture make this historic home a memorable place to stay. This romantic ground floor suite is perfect for couples with a private entrance, queen poster bed, living room, spacious bathroom, individual climate control, heirloom antiques and reserved driveway parking spot. The home is located within the historic district, close to trolley stops and within easy walking distance to downtown. 6 minutes to the beach.

The exterior of the cottage is showcased, featuring a bright blue metal roof, white brick walls, and charming blue shutters. A patio with outdoor seating is visible, surrounded by lush greenery and palm trees under a colorful sunset sky.

4.98 out of 5 average rating, 283 reviews

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.

The sitting room features a blend of warm green and golden hues. A brown leather sofa is adorned with colorful pillows, complemented by a green accent chair. Sunlight filters through the white window blinds, illuminating a vibrant area rug and a piece of art depicting a pelican.

5 out of 5 average rating, 115 reviews

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.

A spacious living room features a light-colored sofa adorned with decorative pillows and a glass coffee table. Two elegant armchairs with floral patterns are placed beside the sofa, and natural light streams through large windows adorned with wooden shutters. A cozy area rug anchors the seating area.

4.95 out of 5 average rating, 207 reviews

Downtown HistoricLuxury • Designer Kitchen & Baths

Off Street Parking for 2 vehicles 2 Min. walk to St George St 5 Min drive to Anastasia State Park Beach 6 Min drive to Fitness Club/Pool High Speed Starlink Internet Luxury Retreat in Historic Downtown. Indulge in a charming vacation rental featuring a spacious living room, gourmet kitchen, and luxury baths. Immerse yourself in the rich history and vibrant culture, with its charming streets and local attractions. Whether seeking adventure or relaxation, this retreat offers the perfect base.

The contemporary two-story home features a modern exterior with a mix of horizontal and vertical siding. A balcony is visible on the second floor, accompanied by a small table and chairs. A fully fenced yard surrounds the property, with palm trees adding to the landscaping.

4.96 out of 5 average rating, 172 reviews

LUX Riberia – 311 | 12-min walk to Historic DTN

LUX RIBERIA COLLECTION - Contemporary, architectural magnificence located in the heart of the eclectic Lincolnville neighborhood in Downtown St. Augustine. Effortlessly explore the Oldest City with a quick 12-min walk into the Historical Downtown for all the top sights, hottest bars & restaurants. Two-story, minimalist style home with double heighted ceilings, fits 6 guests spaciously across the 2 BD, 2.5 BA layout with fully fenced backyard. Views of San Sebastian River perfect for Sunsets.

A spacious waterfront deck offers lounge seating with blue cushions, set against a vibrant sunset sky filled with pink and orange hues. A hammock is positioned nearby, with palm trees framing the stunning view of the water and docks in the background.

5 out of 5 average rating, 141 reviews

Waterfront - Lion’s Bridge & Old Town View

Walk across the Bridge of Lions to downtown St. Augustine with amazing restaurants and attractions. Half a mile to historic downtown! Less than 1 mile to the Castillo de San Marcos fort. Anastasia State Park Beach, the world famous Alligator Farm and Zipline, and the lighthouse are less than two miles away. Several restaurants and bars only a few blocks away. Whether going to the old fort, lighthouse or Flagler College, our home provides a great base for exploring an amazing part of Florida!

4.98 out of 5 average rating, 167 reviews

Uncle Reggie's Beach House

🏝️ Welcome Nights of Lights 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! ✨

A light-filled living area features a modern TV console with a large screen and decorative accents. The space includes a comfortable sofa, two armchairs, and a dining area with a table and chairs, seamlessly connecting to the fully equipped kitchen.

4.94 out of 5 average rating, 112 reviews

Sunshine by historic downtown & the beach

Welcome to Casa Sunshine! A charming home with 2 beds, 2 baths just by historic downtown and near stunning beaches. Fully stocked for cooking, sleeping, laundry & kids' fun. Enjoy beach gear and games, board and mini arcade games for those chill days. Explore historic landmarks, dining, & nightlife, all within walking distance. Unwind in the spacious comfy bedrooms with ample sleeping. Ideal for families or small groups. You'll for sure have an enjoyable and memorable stay in St. Augustine!

A wooden walkway leads from a grassy area to the sandy beach, flanked by two benches on either side. The beach is visible in the distance, with gentle waves and a clear blue sky above.

4.96 out of 5 average rating, 283 reviews

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.

The outdoor area features a spacious patio with paver stones, illuminated by string lights. Comfortable Adirondack chairs are positioned near a hot tub, with a tiki bar and high-top seating visible in the background. The house showcases large sliding glass doors leading to the interior.

4.99 out of 5 average rating, 108 reviews

Coastal Home Steps to Beach w/ Hot Tub & Tiki Bar

★ SEASIDE ESCAPE ★ Newly Updated-This charming coastal inspired home is located one house off the ocean, on a quiet dead-end street in family friendly Crescent Beach ✔ Brand New Beach Walk/Access Across From Home ✔ 10 Person Hot Tub/Spa, New Tiki Bar & Gas Grill ✔ 3 Comfy Bedrooms (Extra 4th Private Sleeping Loft) and 2.5 Full Baths ✔ Short drive to Downtown St. Augustine (15 Min) ✔ Game Garage w/SMART TV, High-Top Table & Foosball ✔ Equipped with 5 SMART TVs and high speed Internet

A hot tub is positioned on the deck, offering a view of the ocean and white sandy beach in the distance. Two houses flank the view, while lounge chairs are visible in the shared yard, contributing to the inviting outdoor space.