House holiday rentals in Anastasia Island

Find and book unique houses on Airbnb

Top-rated house rentals in Anastasia Island

Guests agree: These houses are highly rated for location, cleanliness and more.

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Top Guest favourite

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.

Home in Butler Beach

4.99 out of 5 average rating, 158 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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Top Guest favourite

Home in Butler Beach

4.98 out of 5 average rating, 188 reviews

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! ✨

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Top Guest favourite

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.

Home in Lincolnville

5.0 out of 5 average rating, 144 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.

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Top Guest favourite

The living room is furnished with two light-colored sofas and a central coffee table, creating a spacious and inviting space. A decorative fireplace is framed by mirrors and artwork, while natural light filters in through shuttered windows and greenery adds a touch of nature.

Home in St. Augustine

4.94 out of 5 average rating, 231 reviews

Downtown • Historic Whitney House • Luxury 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.

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Top Guest favourite

A modern home with a distinctive triangular roof stands among lush greenery. A manicured lawn extends in front, bordered by palm trees. The building features a combination of light-colored siding and wooden accents, with a small balcony that adds to its architectural charm.

Home in St. Augustine

4.99 out of 5 average rating, 137 reviews

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.

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Top Guest favourite

A view of the outdoor space showcases a paved patio area adjacent to the home. Two brightly colored chairs and two lounge chairs are positioned for relaxation. A privacy fence surrounds the yard, adorned with tropical greenery and palm trees.

Home in St. Augustine

4.99 out of 5 average rating, 185 reviews

Steps to Downtown, 8 min drive to St. Aug Beach #A

Nestled in a serene residential area, this home offers a tranquil escape just a stroll across the Bridge of Lions to downtown. Enjoy convenient access, with various restaurants, shopping, and nightlife on A1A within a block. Ideal for large families, friends, or couples, the clean, modern space invites relaxation. Explore nearby attractions like miniature golf and the Alligator Farm and more. Leave the vehicle behind and enjoy an stress-free stroll to downtown, avoiding parking issues.

ValueFamilyView

Top Guest favourite

A private saltwater pool is centrally located within a spacious patio area, surrounded by well-maintained grassy lawns. Lounge chairs are positioned alongside the pool, while tables and chairs can be seen in the background. The home features sliding glass doors providing access to the pool area.

Home in St. Augustine

4.97 out of 5 average rating, 107 reviews

Music on Marilyn- Steps from the Amp! •Jacuzzi•

Nights of Lights & mere seconds from the St. Augustine Amphitheater— a short bike ride to the beach and downtown, this modern escape is 3 beds and 2 baths. Welcome to Music on Marilyn! This is the quintessential St. Augustine experience. Nestled on a quiet street that dead ends to the intracoastal, walking distance to the St. Augustine Amphitheater, Lighthouse, Anastasia Park, Alligator Farm and much more! St. Augustine Beach and historic downtown are just a short bike ride away.

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Guest favourite

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.

Home in Butler Beach

4.94 out of 5 average rating, 322 reviews

St Augustine Beachside Home - Walk to Beach

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 about a 10 minute walk 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.

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Guest favourite

The exterior of a modern two-story home is displayed, featuring a mix of light and dark gray materials. A welcoming entrance is accessed by a set of stairs, with landscaped areas visible on both sides, including palm trees and shrubs.

Home in Lincolnville

4.95 out of 5 average rating, 111 reviews

192 Riberia Downtown Luxury Home

Summary: Located in historic Lincolnville neighborhood is this stunning luxury home perched along the tidal marshes of Oyster Creek and just steps from St. Augustine’s historic district. This unique home features a gourmet kitchen, an open living area with Netflix included, a handy workspace, 2 king bedrooms each with a full bath, queen memory foam sleeper sofa and stunning views out to the marsh from the custom windows and decked patio.

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Top Guest favourite

Aerial view of a home surrounded by lush greenery near a waterway, featuring a long dock extending into the water. The structure is illuminated, highlighting the inviting exterior against the twilight sky.

Home in Crescent Beach

4.99 out of 5 average rating, 151 reviews

Gorgeous Views, Golf cart w/beach access!

Beautiful home with outstanding view & access to the Intracoastal. Watch dolphins play, yachts cruise by or catch the sunset from the dock. If you're feeling adventurous, jump on a kayak or paddle board & explore the quaint islands nearby. If the ocean is calling, take a 2 min ride with the included 6 seater golf cart (must sign waiver) & drive right on to Crescent beach. Grab a surf or boogie board for some extra excitement!

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Top Guest favourite

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.

Home in St. Augustine

4.97 out of 5 average rating, 156 reviews

Perfect One Bedroom Cottage in Lighthouse Park

One bedroom one bath cozy cottage vibe! Perfect couples retreat. This is one half of a duplex. The second half is currently vacant. Excellent location. 5 blocks to the lighthouse. 1 mile to historic downtown. 1.3 miles to the Amphitheater. 0.8 miles to Anastasia State park. 3 miles to the St. Augustine Beach Pier. Walking distance to many great restaurants and bars, mini golf, and boutique shops! Walk or bike to downtown!

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Top Guest favourite

A living area features a modern, light-toned sofa paired with a round coffee table. Natural light filters through large windows adorned with red curtains. The open floor plan leads to a dining area, highlighting a connection between spaces with exposed wooden beams.

Home in Lincolnville

4.98 out of 5 average rating, 128 reviews

Historic Lincolnville Retreat!

Step back in time to the enchanting 1920s in our beautifully preserved historic home, nestled in the heart of Lincolnville. This charming residence combines the elegance of a bygone era with modern comforts. Located in a tranquil area just steps away from the iconic Old Town Trolley tour stop, you’ll have easy access to the Lincolnville Historical Museum and other local attractions in walking distance.

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