House holiday rentals in Anastasia Island

Home in St. Augustine Beach

4.99 out of 5 average rating, 179 reviews

Beachside, SUPER CLEAN, Oasis Yard, Summer Retreat

"We had an absolutely fantastic time staying at Dominick’s place. From start to finish, everything exceeded our expectations" * 100% 5-star rating ⭐ * Less than 500 steps to St Augustine Beach! ⛱️ * Super comfortable and meticulously clean. ✨️ * Huge Private Oasis Backyard, BBQ, Speakers, LOTS of seating 🌴 * towels + beach chairs + beach cart ⛱️ * 100% cotton sheets and towels ☁️ * comfy beds, pillows, extra pillows + blankets, living room * Fully stocked kitchen * On the Golden Mile

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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.

4.99 out of 5 average rating, 163 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.

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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, 320 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.

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4.98 out of 5 average rating, 158 reviews

A coastal cottage with a modern design features a light-colored exterior and a metal roof. The entryway is adorned with teal shutters and a bright front door. Two white adirondack chairs are positioned on the porch, surrounded by well-maintained landscaping and palm trees.

Home in Crescent Beach

Seaside at Crescent Beach, 150 steps to the ocean

150 steps to beach sand of the ocean. SEASIDE beach cottage, built in 2021, at A Avenue - At the ramp to Crescent Beach ( 32080) 5 miles south of St. Augustine Beach. 20 minutes to The Nation's Oldest City. Great restaurants in the area. Rent a kayak -Boat ramp, fishing outfitter 3 blocks away. Open floor plan 2 story 3 br. and loft and 2 1/2 baths and a laundry room. Master BR downstairs. Soaring ceilings , good variety of space. Great vacation/family get-together spot. 2 Porches .

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The two-story beach house is framed by a lush green lawn and palm trees, featuring a spacious front porch with white chairs. Large windows and a gabled roof enhance the inviting appearance. A clear blue sky serves as the backdrop.

4.9 out of 5 average rating, 180 reviews

Beach & Serenity; The Perfect Location in St. Aug

Forget your worries in this spacious and serene space. Beautiful beach house 6 blocks to beach, 2 blocks to intercoastal Drive on to the beach at one end of the street, Easy walk to the best sunsets at the marsh Restaurants at each end of the street Upstairs and downstairs screened porches *PLEASE NOTE, AND THIS IS IMPORTNAT * We cannot split weekends. Friday and Saturday nights booked together *ONE PET PER STAY W/ APPROVAL *no washer/dryer available, hang dry only *STRICT CHECK IN/OUT TIMES

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Guest favourite

A modern home is surrounded by a well-kept backyard featuring a private pool and spacious patio. Comfortably arranged lounge chairs provide a relaxing spot. The exterior showcases light-colored siding and elevated balconies, with palm trees dotting the landscape for a tropical feel.

4.89 out of 5 average rating, 116 reviews

Sunset Cove 2 - Pool - Sea Views - Walkable

Stunning new luxury 2br/2.5ba pool home with peeks of Salt Run and Anastasia State Park: * Pool Heat Available for $30 per day - Contact us after booking for details * Private pool + backyard * Parking for 3 cars * 2 king bedrooms w/ en-suite bathrooms & smart TVs w/ Netflix * 2 min drive (or 20 minute walk) to historic downtown St. Augustine * 2 min drive to the beach (Anastasia State Park) * 5 min walk to lighthouse, Alligator farm, restaurants & bars * Fully stocked and equipped kitchen

LocationFamilyCleanliness

Guest favourite

Home in St. Augustine Beach

4.87 out of 5 average rating, 246 reviews

St. Aug Oceanfront Home w/ Heated Pool & Firepit

Just steps from the ocean and a 10-minute drive to historic downtown St. Augustine, this one-of-a-kind 1970s pink three-story A-frame is the perfect backdrop for your next vacation, bachelorette party, or relaxing getaway. Inside, you’ll find a bright, cheerful space—ideal for popping mimosas in the morning or unwinding after a sun-soaked day with private beach access. Whether you're staying for the weekend or the season, you're sure to make lasting memories. I can’t wait to host you!

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4.94 out of 5 average rating, 235 reviews

Downtown • Parking for 2 + Wraparound Porch

Historic Whitney House • Newly renovated 1,700 sq ft designer home Private driveway parking for 2 • Steps to trolley & St. George Street Gourmet kitchen, 2 en-suite bedrooms, 3 luxury baths, Starlink WiFi, wrap-around porch + sunny deck. Fitness club & pool passes included. Modern luxury in the heart of historic downtown St. Augustine. Perfect for couples or small groups seeking modern luxury, easy parking, and a walkable base right in the heart of historic downtown St. Augustine.

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The exterior of Casa Coquina is presented, featuring a charming façade with rounded archways. A light blue garage door complements the neutral-colored walls. Lush greenery, including palm trees and decorative plants, enhances the inviting entryway, while a driveway leads to the garage.

4.99 out of 5 average rating, 139 reviews

Casa Coquina Walk to Downtown Clean Quiet Spacious

Casa Coquina offers a uniquely central location for your visit to the nation's oldest city. Located across from Salt Run Waterway & walking distance to many restaurants & entertainment, this newly renovated home offers 2 bedrooms & 2 full bathrooms, large living room, Florida room & outdoor patio. It is a 2-minute drive to Historic Downtown & 5-minute drive to our beautiful beaches. The huge tree-shaded yard is completely fenced in for child/pet safety & total privacy. Enjoy!

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Home in St. Augustine Beach

4.96 out of 5 average rating, 108 reviews

A- Street Beach Cottage!

Park and NEVER drive again on St. Augustine's most coveted beach street. Immerse yourself in serenity at our A-Street Beach Cottage, the ultimate destination for a stress-free, walkable beach getaway. Our cozy retreat offers unparalleled convenience and is steps away from various amenities. With the beach a mere 75 steps from your doorstep, relaxation is effortlessly accessible. Our driveway can accommodate 2 vehicles only, no trailers. No pets Reserve your beach bliss!

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A spacious living area features a dark blue sectional sofa with accent pillows, set on a wooden floor. To the left, a sliding door leads to a screened-in porch. Natural light illuminates the open-concept layout connecting the kitchen and dining areas with a central bar counter and stools.

4.99 out of 5 average rating, 100 reviews

Steps to Beach~Family & Pet Friendly~St Augustine

🏄‍♀️ Kon Tiki — Your Surfside Escape Step into salty breezes, sandy toes, and pup-friendly vibes at this laid-back 3BR/2BA beach house 🌴 just a 7-minute stroll to Butler Beach. Designed for families and friends, Kon Tiki blends space, comfort, and coastal style with thoughtful touches that make vacations effortless. From morning coffee on the porch to sunsets by the shore, it’s all here. ✨ Book weekly or monthly stays and unlock exclusive discounts!

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A dining area is featured with a blue table at its center, surrounded by four wooden chairs with woven seats. Natural light filters through bamboo shades on the windows, highlighting a wooden sideboard displaying beach-themed decor.