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

19 Oct - 20 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

includes taxes & fees

19 Oct - 20 Oct

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

8 Oct - 9 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.

includes taxes & fees

27 Oct - 28 Oct

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.

includes taxes & fees

13 Oct - 14 Oct

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

8 Oct - 9 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

8 Oct - 9 Oct

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Top Anastasia Island Hotel Reviews

Best Western Seaside Inn

10/10 Excellent

"Great Hotel in St Augustine Beach , not far from St Augustine Pier. Great breakfast and coffee . Rooms in excellent condition."

Hampton Inn St. Augustine Beach

8/10 Good

"We had a wonderful stay at Hampton. Abagyl and Vanessa were both extremely helpful and went above and beyond to assist us with upgrading our room and arranging trolley tickets. Their friendly and attentive service made our stay even more enjoyable. The only disappointment was that the boiled eggs at breakfast were not peeled, which was a minor inconvenience. Overall, we thoroughly enjoyed our stay and appreciate the excellent hospitality we received. We would be happy to stay here again!"

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