Anastasia Island Cottages

A wooden pier extending into calm water at sunset.

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Our top choices for Anastasia Island cottages

A white house with a garage, surrounded by a garden with various plants and a small patio area.

1. < 1 Mi to Butler Beach! Home w/ Dog-friendly Yard

Butler Beach

includes taxes & fees

25 Oct - 26 Oct

A small red house with a white door, a porch with a striped umbrella, and a mural on the wall.

2. The Red Cottage ~ 5 min. stroll to Historic St. George Street - on site parking

Uptown

Paige F.

includes taxes & fees

12 Oct - 13 Oct

A covered outdoor seating area with a hot tub, a wooden deck, and a small building with a door and windows.

3. Casita Isabella | Private Hot Tub in the Pines

St. Augustine

A building with a sign for 'Krispy Gallery' and another sign with a clock. There are potted plants outside and a bicycle parked on the sidewalk.

4. Charming 2/2 Cottage ~ Walk to Historic Downtown

Downtown Historic District

includes taxes & fees

27 Oct - 28 Oct

A wooden deck with a hot tub, a pool, and outdoor furniture.

5. Casa Caliente | Plunge Pool, Screened Spa & Two Queen Lofts

St. Augustine

Jamie H.

A single-story house with a porch, a small garden, and a visible garage door.

6. Historic St. Aug, Top Rated, Walkable, Rare Free Parking & Pets

Downtown Historic District

Richard W.

A wooden deck with a hot tub and a sofa with red cushions.

7. Luxury Tiny Home with Private Hot Tub — 3 Miles to Historic St. Augustine

St. Augustine

Drew R.

includes taxes & fees

12 Oct - 13 Oct

A modern kitchen with a double sink, a dining area, a gray sofa, and a yellow door.

8. Adorable cottage central to everything

Ravenswood

Janice H.

includes taxes & fees

9 Oct - 10 Oct

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Top Anastasia Island Hotel Reviews

La Fiesta Ocean Inn And Suites

10/10 Excellent

"This is our go-to place to stay in St. Augustine Beach, great staff, and close to great restaurants!"

voco St. Augustine Historic Area by IHG

10/10 Excellent

"We always enjoy the VOCO in St Augustine. It’s a more adult like setting. Small quaint rooftop pool with Cabanas and sofas. Staff is great, rooms are clean, beds are comfy. Available transportation from hotel to Ampitheater or Historic District for small cash price. Fun place."

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