Pillars' Castle

Huge Historic Home Perfect for Special Occasions Steps to Sites, Shops, Restaurants, 3 Master Suites

4 BR
4.5 Baths
Sleeps 10


We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination!

If you are coming to celebrate a special occasion, or just enjoy historic St. Augustine with family or friends, Pillar's Castle is the perfect place to do so! Pillars’ Castle is a beautiful century old home in the heart of St. Augustine, a perfect setting for families and groups coming to explore in the Old City. If you are coming for a wedding or another event nearby, this historic home with large bedrooms and 5 bathrooms is a fun and well-equipped place to enjoy together and get ready for your event! In addition, artists and historians alike will flock to this Spanish Moorish castle complete with storied pedigree. Once the home of famed sculptor C. Adrian Pillars, this impeccably appointed home offers luxury on a grand scale and features 4 bedrooms, 3 of which Master Suites, a newly updated kitchen with island and dining area, a formal dining room seating up to 10 people, a huge living room with baby grand piano and throne, perfect for photo memories, a casual den with large TV, a pool table game room overlooking the grand living room, and outdoor garden. Plenty of parking is available on the long driveway and parking pad in the rear of the home, along with a convenient exit to a rear street.

Located in one of St. Augustines historic housing districts bordering the Matanzas River, you will find the neighborhood a beautiful place to walk and enjoy Revival period architecture and ancient oaks. A small park located at the end of the street gives views over the marsh along the river where you can watch the ospreys fish. Just a few minutes' walk away is famous Magnolia Avenue, a favorite photo spot lined with majestic oaks, where you can enter the Ponce de Leon Fountain of Youth Archaeological Park and explore the original St. Augustine settlement location and marvelous views of the river. Also in close walking distance is the Mission Nombre de Dios with "The Great Cross," and numerous "Uptown" boutique, antique, and coffee shops. A one mile walk will take you to the Castillo de San Marcos, the riverfront, and famous St. George Street with numerous spectacular restaurants. When you are ready to enjoy some sun and surf, rent some bikes and take a 1.5 mile ride over the Vilano bridge to the beach and the quaint beach-side town of Vilano Beach.

A rear patio welcomes you into the Grand Hall of Pillar's Castle, with the kitchen, den, dining room, laundry room, bathroom, plus powder room located on the first floor. The large "St. Augustine Surf" bedroom is located off the kitchen area and up several steps and near the bathroom. Take the Grand Staircase to the second floor where the Game Room is located, along with two luxurious Master Suites, one with an adjoining kitchenette which also opens to the hall, making it accessible to the Game Room. Up another flight of stairs to the third floor, you will find the fourth bedroom which is equipped with two full-sized beds and a sitting space.


- Unique Moorish Castle with oversized living and sleeping spaces

- Updated Kitchen

- Pool Table Game Room

- Wifi, Ethernet

- 52" HDTV with Chromecast, Netflix, Roku

- 3 Master Suites, Kitchenettes w/Keurig accessible to each bedroom

- Separate Wet Bar w/Wine Cooler

- Separate Ice Maker

- Mini Fridge and Freezer

- Keurig and Regular Coffee Pots

- 2 Dining Spaces

- Baby Grand Piano

- Historic Furnishings

- Library

- Children's Games and Books

- High Chair and Travel Crib

- Workspace

- Starter Bathroom Amenities

- Bathrobes in Primary Master

- Starter Coffee

- Driveway Parking Holds up to Six Cars

Take the Old City Trolley Tour around the area and take in the historic beauty of Downtown St. Augustine! Explore the oldest fort in the continental United States, the Castillo San Marcos, and stroll down colorful St. George Street filled with shops and restaurants of irresistible local flare. You might even spot a Pirate or Spanish Conquistador in period attire! Breathe in the warm, salty air as you enjoy a romantic walk along the waterfront as the sun sets, casting its final rays on the sparkling water, the drifting boats, and the picturesque Bridge of Lions. But don’t forget to make good use of the night by experiencing the Ghost train or Haunted House tour. Enjoy the endless variety of restaurants, coffee shops, ice cream, art galleries and book stores just steps from your front door!

Our FREE FUN! package is included in your booking with one free entry per attraction each day of your stay! The following attractions are included;

- St. Augustine Alligator Farm

- Old Town Trolley Tours: Potter's Wax Museum

- Old Town Trolley One Day Tour

- Old Town Trolley Ghost and Graveyards Tour

- Royal St. Augustine Golf & Country Club Course

- St. Augustine Pirate & Treasure Museum

- St. Augustine Eco Tours: Boat Expedition

- St. Augustine Eco Tours: Salt Marsh Kayaking

This is a new listing that has been enjoyed already by numerous guests! These are a sampling of the recent great reviews:

Benjamin, October 2023 - Great stay! Super clean, super spacious, wonderful place to stay for a wedding or family function.

Steven, June 2023 - The home is rich in history and beauty. I highly recommend staying here for an event or just a luxurious trip.

Brittany, April 2023 - Had a wonderful stay. Kids really enjoyed the scavenger hunt around the house. Wonderful place for a family get together.

Evita, March 2023 - The stay here was so beautiful , so close to downtown and all the hot spots but far enough to where you can enjoy a peaceful sleep . Love it would stay again

Jeana, March 2023 - The castle was even more beautiful than we expected. The bedrooms were all very comfortable. We had a wonderful visit for Dad's 80th birthday! He felt like a King! We will definitely visit again!

NOTE: $500 cancellation fee applies to all bookings 28 days or more.

Startup bathroom, kitchen, and laundry supplies are provided with each booking.

25 year age requirement to book and stay: Tenant must be at least twenty-five (25) years of age (an "adult") and will be an occupant of the unit during the entire reserved dates.

16 May St St. Augustine, FL 32084

Sleeping Arrangements

Master 1 King
Master 2 King
Master 3 Queen
Bedroom #4 Queen (2)

Property Rules

Check In: After 4pm
Check Out: Before 10am
Smoking: Not Allowed


Air Conditioning
Bed linens
Big Screen TV
Bird Watching
Board Games
Carbon monoxide alarm
Carbon monoxide detector
Central air conditioning
Children Welcome
Cleaning Disinfection
Cleaning products
Clothes Dryer
Common Surface Disinfectant Cleaned
Cooking Basics
Dedicated Workspace
Dining Table
Dishes Utensils
Dishes and Silverware
EV charger
Eco Tourism
Enhanced Cleaning
Enhanced Cleaning Practices
Family Friendly
Fast Wifi
Fire Extinguisher
First Aid Kit
Free Parking
Free Wifi
Free parking
Full Kitchen
Game Room
Garden Or Backyard
Garden Patio
Hair Dryer
High chair
Hot Water
Ice Maker
Internet Access
Iron Board
Living Room
Minimum Age Limit
Near Ocean
Outlet Shopping
Pets Not Allowed
Pool table
Portable fans
Private entrance
Private patio or balcony
Requires Stairs
Self Check-In
Shower gel
Smart TV
Smart Tv
Smoke Detector
Towels Provided
Wildlife Viewing
Winery Tours
Wireless Internet
private entry


Frequently Asked Questions

For your safety, the weight limit for bunk beds is 100 pounds.

Minimum $500 Fee for House Rule Violations


Please report any maintenance needs for the premises to the us and we will respond as quickly as possible. Refunds will not be made for maintenance issues including, but not limited to heating and air conditioning, appliances, televisions, and stereos.  Check out instructions as provided must be complied with.


Tenant and all other occupants willingly occupy these premises.  In exchange for being allowed to occupy the premises, Tenant, on behalf of himself, his heirs, assigns, and descendants, agrees to the fullest extent permitted by law, to release and forever discharge  iTrip or the Owner from any and all injuries, costs, damages, loss, death, or other claim or injury suffered of any nature whatsoever arising out of Tenant’s own negligence or gross negligence; the negligence or gross negligence of  the Owner or iTrip or any of its employees, managers, principals, owners, representatives, agents, authorities, leaders, or other person affiliated with it in any way; and the negligence or gross negligence of any other occupant in connection with the stay whether that be prior to, during, or immediately after the stay. By agreeing to these terms, and in exchange for being allowed to stay on the premises, you further agree that you will indemnify iTrip and the Owner and hold iTrip and the Owner harmless for any and all injuries, costs, damages, loss, or other claims made by all other occupants other than yourself arising out of or in any way caused by your actions undertaken in the course of your stay on the premises. Tenant understands that he/she does not have to stay on the premises and that without agreeing to these terms whereby he/she chooses voluntarily to waive any liability of iTrip and the Owner under the above terms, he/she will not be allowed to stay on the premises.

Clicking the box below provides consent to receive text communication from iTrip St. Augustine relating to your reservation.  Guests can opt out of this text communication at any time by following specified opt out procedures.

25 year age requirement to book and stay: Tenant must be at least twenty-five (25) years of age (an "adult") and will be an occupant of the unit during the entire reserved dates. 

We hope you enjoyed your stay! Check Out Time is at 10:00 AM! But before you leave, be sure to:

  • Please empty the refrigerator.

  • Place all dirty dishes in the dishwasher and start the cleaning cycle.

  • Please do not strip sheets but leave beds unmade.

  • Pile all dirty towels in the bathroom or laundry room.

  • If you have rearranged any furniture or placed any items out of sight, please put them back as they were when you arrived.

  • Please be sure to collect all of your belongings.

  • Please remove all trash and place it in the respective trash recepticle. 

*Please be considerate of the check out time since the cleaners need to get in to prepare the property for the next guests. A delay in check out will result in a charge of additional fees. Thanks so much and we hope you will come again soon!

Guest violation of house rules will result in a minimum $500 fine.
For pet friendly properties, pets must be approved prior to booking.  Request approval with number, size and breed.  A pet fee and/or pet deposit will apply.  Do not leave dog unattended in house unless in kennel. If you bring a pet to a non-pet friendly property, you will be subject to our $500 fee for house rule violation! 


Castle is everything
5/5 stars
One of the best trips ever. Best place I've ever stayed.
- Corey

Corey, thank you for your review and stay. We are so glad you had the best trip ever in our castle! It is a special place! It was a pleasure hosting you and we would love to have you back!

- Manager Response
Fun with friends
5/5 stars
Pillars castle is so beautiful and unique. Everything about this lovely historic building is educational as well as a plush living space for your vacation. Each bedroom is an enjoyable peaceful resting place and the main rooms provide every amenity you need for games chatting with friends and family the grand piano and the pool table room are very chic. My friends and I had a wonderful time. The castl is very convenient for visiting the downtown as well as other areas of scenic st Augustine.
- Rosemary

Rosemary, thank you for your kind review. We are so glad you enjoyed staying in our castle! It is definitely a unique home in the perfect location for relaxing and exploring St. Augustine. It was a pleasure hosting you and we would love to have you back!

- Manager Response
We loved the castle!
5/5 stars
The Pillars Castle was amazing! We absolutely loved and enjoyed our stay with our family! It’s about a mile from the “action” of downtown but a lovely walk with things to stop on on the way. Literally around the corner from the fountain of youth. The property was beautiful and the house was clean and spacious!
- Courtney

Book Your Stay

Select your trip dates.
Contact Manager

Phone (904) 824-9974