Condo

The Gregory.. Old Florida Charm on Anastasia Island Near Historic St. Augustine

Photo gallery for The Gregory.. Old Florida Charm on Anastasia Island Near Historic St. Augustine

A covered outdoor seating area with artificial grass, white chairs, and string lights.
A modern kitchen with stainless steel appliances, wooden cabinets, and a dining area with a table and chairs.
A living room with a sofa, two armchairs, a coffee table, and a painting on the wall.
A kitchen with a stainless steel refrigerator, a wooden table with baskets, a coffee maker, and a wall-mounted wooden wheel.
A bedroom with a wooden bed, a bedside table with a lamp, a window with curtains, and a view of the outdoors.

Reviews

10 out of 10
Exceptional

Highlights

  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
  • Discover nearby landmarks
    Walk to Bridge of Lions

Popular amenities

  • Dog-friendly
  • Air conditioning
  • Refrigerator
  • Washer
  • Internet
  • Onsite parking available

Explore the area

View in a map
St. Augustine, FL
  • Place, Anastasia Island Mini-Golf
    ‪7 min walk‬
  • Place, St. Augustine Lighthouse & Maritime Museum
    ‪12 min walk‬
  • Place, St. Augustine Alligator Farm Zoological Park
    ‪15 min walk‬
  • Airport, St. Augustine, FL (UST-Northeast Florida Regional)
    ‪12 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Living Room 1

1 Queen Sofa Bed

1 bathroom

Bathroom 1

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Spaces

Porch or lanai
Kitchen
Number of living rooms
Dining area

Add dates for prices

Similar properties

Property grounds
Lighthouse Loft l Marshfront l Walk to Downtown
Davis Shores
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
10.0 out of 10, Exceptional, (7 reviews)
Lighthouse Loft l Marshfront l Walk to Downtown

About the neighborhood

St. Augustine

Davis Shores, a neighborhood in St. Augustine, is home to this condo. Castillo de San Marcos National Monument and Lightner Museum are notable landmarks, and travelers looking to shop may want to visit St. George Street and St. Augustine Premium Outlets. Ready for a night out? Consider The Conch House Restaurant and Castle Otttis.
Map
St. Augustine, FL

What's nearby

  • Anastasia Island Mini-Golf - 7 min walk - 0.7 km
  • St. Augustine Lighthouse & Maritime Museum - 12 min walk - 1.1 km
  • Bridge of Lions - 13 min walk - 1.1 km
  • St. Augustine Alligator Farm Zoological Park - 15 min walk - 1.3 km
  • St. George Street - 3 min drive - 1.7 km

Getting around

  • St. Augustine, FL (UST-Northeast Florida Regional) - 17 min drive

Restaurants

  • ‪Harry's Seafood Bar Grille - ‬18 min walk
  • ‪Circle K - ‬5 min walk
  • ‪Conch House Restaurant - ‬8 min walk
  • ‪Casa Reina - ‬18 min walk
  • ‪Tradewinds Tropical Lounge - ‬18 min walk

Frequently asked questions

Is The Gregory.. Old Florida Charm on Anastasia Island Near Historic St. Augustine pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 50 lbs per pet.

How much does it cost to stay at The Gregory.. Old Florida Charm on Anastasia Island Near Historic St. Augustine?

As of Nov 9, 2026, prices found for a 1-night stay for 2 adults at The Gregory.. Old Florida Charm on Anastasia Island Near Historic St. Augustine on Jan 4, 2027 start from $156, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Onsite parking is available at the property.

What time is check-in at The Gregory.. Old Florida Charm on Anastasia Island Near Historic St. Augustine?

Check-in begins at 3:00 PM.

What time is check-out at The Gregory.. Old Florida Charm on Anastasia Island Near Historic St. Augustine?

Check-out is at 11:00 AM.

Where is The Gregory.. Old Florida Charm on Anastasia Island Near Historic St. Augustine located?

Located in Davis Shores, this condo building is within 1 mi (2 km) of Matanzas River, Flagler College, and Castillo de San Marcos National Monument. Anastasia State Park and St. George Street are also within 2 mi (3 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
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Rating 10 - Excellent. 1 out of 1 reviews
Rating 8 - Good. 0 out of 1 reviews
Rating 6 - Okay. 0 out of 1 reviews
Rating 4 - Poor. 0 out of 1 reviews
Rating 2 - Terrible. 0 out of 1 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean and super convenient to downtown
Stayed 2 nights in Nov 2026
Response from VrboOwner on Nov 9, 2026
Thank you, Carol! We’re so glad you enjoyed your stay at The Gregory! It was a pleasure hosting you, and we would love to welcome you back for another visit. As a token of our appreciation, we’re happy to offer you an exclusive returning guest discount on your next stay! Whenever you're ready to plan another getaway to St. Augustine, feel free to reach out to us directly, and we’ll be happy to provide you with a special rate. Thank you again for choosing The Gregory. We hope to see you again soon! Warm regards, The Gregory Your Old Florida Getaway
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