Orange Street Apartment

Victorian Apartment Steps to Old City Attractions, Free Parking

2 BR
1 Bath
Sleeps 4


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!

Enjoy all of the St. Augustine downtown area attractions from this ca. 1887 victorian second floor apartment! Restaurants, bars, shops and attractions are all within walking distance of the home. Guests have access to the rear deck with grill and high-top table, as well as the side covered porch with two seating areas. The main living area of this apartment is an open living, dining, and kitchen combination space. Both bedrooms are spacious and the bathroom is completely updated. Enjoy antiques throughout the home, and traditional decor. The kitchen is stocked with all you need to cook "at home," or enjoy a quick lunch on the go. The bathroom and bedrooms are outfitted with soft towels and crisp linens.

Sleeping Arrangements (4):

-King Bedroom

-Queen Bedroom


-Free, Private parking in lot behind home (shares lot with realty and accounting offices below and next door)

-Full Kitchen

-Smart TV


-Washer and Dryer

-Linens provided

-Keyless entry

-Walk to area restaurants and attractions (5-10 min.)

-3 miles to Anastasia State Park

-3 miles to Vilano Beach

-5 St. Augustine Beaches at St. John's Ocean Pier

**PET POLICY: Only dogs are permitted, and must be approved by management PRIOR to booking. You must inquire with the number, weight, and breed to get approval before you book as some breed and size restrictions apply. A pet fee will be required upon approval.

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

Let iTrip help you make the most of your vacation!

Reservations 28+ days do not include the Free Fun package. Tickets may still be available at the discretion of the property manager.

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

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

101 Orange St St. Augustine, FL 32084

Sleeping Arrangements

East Room King
West Room Queen

Property Rules

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


Air Conditioning
BBQ Grill
Big Screen TV
Carbon monoxide detector
Clothes Dryer
Coffee Maker
Covered porch
Dishes and Silverware
Enhanced Cleaning
Fire Extinguisher
Free Parking
Free parking
Full Kitchen
Gas Grill
Hair Dryer
Internet Access
Self Check-In
Smoke Detector
Washing Machine
Wireless Internet
private entry
Family Friendly



Frequently Asked Questions

Minimum $500 Fee for House Rule Violations


In the event that you must cancel your reservation, please be aware that we adhere to the Airbnb policy as follows: 

  • Guests can cancel at least 30 days before check-in and get a 50% refund of the nightly rate and the cleaning fee, but not the service fee. 

There will be no refund for early departure unless authorities request mandatory hurricane evacuation. Vacation Insurance is recommended.


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.

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! 


5/5 stars
101 Orange Street Apartment, is great loved the space and location to Old Town St. Augustine
- Danna

Danna, We strive for an excellent guest experience, and we are glad to hear we met those expectations for you during your stay with us! We hope to have the opportunity to host you in the future!

- Manager Response
Great Place
5/5 stars
This rental was a great vintage place to be. Very cozy and very clean. 7 minute walk to downtown St. Augustine. Lots of antique furniture. The beds were huge and very comfortable. The couch was not. It had more Pans and kitchen utensils then a place in Daytona that we stayed that costs us over $2000. There was only ONE thing that we did not like and that was the very steep steps to get up-and-down to the apartment. I took pictures but I don't see a place to post them. Not suitable for someone who is handicapped or can't safely climb stairs. Other then that we Loved it.
- Robert, Diane and Ronnie

Robert, Diane and Ronnie, We are so pleased you enjoyed your stay with us at Orange Street Apartment, and that you had everything you needed to have a successful trip! We'd love to have you back soon!

- Manager Response
Awesome Place to Stay
4/5 stars
This was a great place to stay! Walking distance to attractions. Quiet. Quaint. Very homey. Perfection!
- Heather

Thank you for staying with us, Heather! We are glad to hear that you felt at home and enjoyed your stay.

- Manager Response
Quick trip
4/5 stars
Don’t let the out side fool you !!! This place has character. We loved it. The bedrooms are roomy the living room kitchen combo have plenty of space. The bathroom is up to date. We attended a wedding at the fountain of youth during our stay and we’re able to walk back that night with ease If your planning on walking to the main down town area it’s about 30min walk but will save you on expensive packed parking lots. Hanna and the team at Itrip were amazing to deal with. I’ll be looking to use them for our next trip as our first option when looking for places to stay.
- Daryl
Road Construction
3/5 stars
The location of this property is wonderful walking distance with free parking to downtown. Unfortunately, we also had issues with road construction that shook the building from 12-5am and with 2 small kids that did not sleep, the next day was rough. We reached out to the company before booking and was told drilling should be complete by the time of our stay. We also reached out during our stay when this occurred, but received nothing as previous visitors had stated. If you are a light sleeper bring a sound machine (road noise is also very loud) or do not book, you will not get sleep while the construction continues. The floors need a really good cleaning. Location and parking a plus. Cleanliness and external noise leave much to be desired. The company did respond quickly to all messages.
- Caroline

Caroline, we apologize for the construction noise that you experienced. Unfortunately, we have no control over when they come and go doing the road construction. We will address the floors with the cleaner. We are glad you stayed with us!

- Manager Response
Convenient to Historic District, but has issues
3/5 stars
This apartment is on the second floor of a fairly old residential building; the lower floor is occupied by a chiropractor. On arrival you can park one vehicle in the assigned space at the rear of the building, which is a great benefit in this parking-challenged city. Access to the second floor is via a narrow and steep staircase that is unsuitable for anyone with limited mobility, and for young children. The apartment itself consists of two bedrooms, a small but adequate bathroom, and a main room with kitchen, table, and seating. There’s modern kitchen appliances and a large-screen Samsung TV. The TV service is by Dish Network and internet/wifi by Comcast Business. The bedrooms are basic, but have very comfortable beds and smaller-screen TVs. The furnishings and decor are decidedly “antique-style” and will not be to the taste of everyone. The kitchen has just about everything you would need if you want to self-cater; mugs, plates, glassware, cookware , silverware, etc. The apartment seems well maintained and mostly clean, though when I was there the floors throughout were very dirty, and I had to resort to wearing shoes at all times. Realtors will tell you that “location” is everything, and that’s a double-edged sword for this apartment. On the positive side, it’s at the northwest corner of the historic district, and a 10-20 mile walk will get you to all of the key restaurants and attractions downtown. On the negative side, it’s within yards of the US-1 highway, and just beyond that is the Florida East Coast Railway line. Traffic and freight trains trundle through 24/7, and the whole building shakes at times. You’ll need to be a sound sleeper to sleep in the West bedroom, immediately overlooking the highway. In summary, this is a convenient downtown accommodation but it comes with several issues.

Brian, thank you for the feedback. We will address the floors with the cleaner! Thank you for staying with us!

- Manager Response
Easter weekend trip
5/5 stars
We really loved the location and ambience of 101 orange street. The size was perfect for our short trip. There are a few supplies we recommend you get for future guests: - a hand towel for use in the kitchen - an additional towel rack in the bathroom, for multiple guests to use -a few more mirrors throughout the apartment -a mop and broom to clean the floors Best wishes.
Orange St. Snowbird
5/5 stars
This is the second time I stayed in this apartment. I love the apartment, I love the location, and I love that I can bring my dog. Some of my favorite things are, 1. it is walking distance to everything 2. there’s free parking, and 3. the only other tenants in the building are a very nice chiropractic practice. Tomorrow I head back north, and I’m already thinking about how much I can’t wait to return. I have very little need to communicate with iTrip vacations, because everything was perfect. I was contacted early on the day of my arrival. It was by text from Olivia. She let me know that I was able to access the apartment early. The only other time I needed to contact them was, I experienced a brief Internet outage. As it turns out, the entire neighborhood was out. My text was returned within a minute or two, and they were contacting maintenance immediately.
- Mark

We are so pleased to hear about your great experience staying with us Mark! We can't wait to host you again in the future!

- Manager Response
3 day st. Augustin getaway
5/5 stars
My husband and I had a wonderful visit to st Augustin and your rental was perfect. We had everything we could need. Bed was super comfy and decor was very nice in the bedroom.location was perfect, easy walk to everything.
- Sally

Thank you, Sally, for the kind review! We are so glad that it was perfect for you. We hope you come again!

- Manager Response
Great location
5/5 stars
This place was in a great location with easy walking to all the sights of old town. Clean with comfortable beds and plenty of space for 4.
- Kelly

Kelly, We are so pleased to hear you had a great stay at Orange Street Apartment and enjoyed the convenient location. We hope you will come again sometime soon! Thanks so much for the great review:)

- Manager Response
Better than a hotel.
5/5 stars
Orange street apartment is a great rental with lots of space and a great location. Perfect rental for 4 people. Bedrooms are spacious and beds are comfy. Bathroom is updated and has body wash, shampoo and conditioner for everyone. Living area has a nice table and chairs, couch and rocking chair. Plenty of room to wake up and relax, or settle down at the end of the day. Kitchen has everything you need and a full size fridge. Location is a few blocks from the fort and the st George street. Lots of restaurants within easy walking distance.
- Michael

Michael, Thank you so much for this kind review of Orange Street Apartment. We are so pleased to hear that you had a great stay. We hope you will consider coming again sometime:)

- Manager Response
Lovely stay
5/5 stars
Great location (10/10), walking distance to most of the places we wanted to go. Pet friendly, which was key for us. It was clean (9/10).
- Eric

Eric, We are so glad you had a great stay at Orange Street. Thank you so much for the great 10 out of 10 review and feedback! We hope you will come again soon!

- Manager Response
Lovely Place
5/5 stars
The 2/1 is lovely has an antique style with updated accessories. It’s in a great location to walk to historic downtown St. Augustine and is within a 5 minute drive to anything you could possibly want from the area. Close enough, yet not to close. You won’t be kept up at night from restaurants in the district, etc. However, it is next to the main road and you will hear traffic. It didn’t bother us and we had a great time. The rooms were very clean and had a wonderful time. We were there for a firefighters’ convention this year and we will definitely return to this apartment next year. Thanks for everything.
- Dwight

Dwight, Thank you so much for leaving a great review of Orang Street. We are pleased to hear you enjoyed your stay! We hope to host you again sometime soon!

- Manager Response
10/10 recommend
5/5 stars
Location was amazing! Walking (12 mins) down Orange St. takes you right onto St George St. and into the downtown historic district. You will avoid having to pay for and hunt for parking which is HUGE in itself. The house was beautiful and came equipped with everything needed (iron and ironing board included but not listed under amenities). The furniture and antique items in the house were lovely. The entry stairs are a tad steep, but manageable. I even brought my senior pup along and she was very comfortable. Only cons to report, the shower’s hot water goes in and out a few times but then stays steadily hot after about 2-3 times of doing this. Second, the road/ train noise is noticeable since the house sits right on Ponce De Leon (I used my sound machine app and had no problems). The trains roll through quite constantly and it makes the house/ beds wobble and sway a little.. It took me two days to realize my room wasn’t haunted haha. Third, there is only one parking space for the apartment, but there is street parking available. The tree above the parking spot gives off a terrible sap that covered my car and windows just FYI! Overall a wonderful place to stay! Would definitely consider staying again in the future. Thank you!
- Samantha
10/10 stay
5/5 stars
Amazing property, very organized and homely with owners that's clearly care for the residents stay.
- Noah

Noah, Thank you so much for this great review of Orange Street Apartment! We are happy to hear that you had an amazing stay! Hope to host you again soon!

- Manager Response
Charming and Convenient
5/5 stars
We spent a long weekend at Orange Street Apartment and enjoyed it very much. It is upstairs and the steps up are slightly steep but were no problem. It is about 4-5 blocks to historic St. Augustine. There is not much parking in the historic area unless you use the parking deck at the Visitor’s Center, but we enjoyed walking to the shops and attractions. We loved the antiques in the apartment and the accommodations were comfortable with the exception of the inadequate hot water in the shower. We found some great restaurants in the historic area while also being right around the corner from several fast food places. We would definitely love to stay there again!
- Edwin

Edwin, We are so glad you loved your stay at Orange Street Apartment. We are pleased that you enjoyed the decor and the location. We hope to host you again soon! Thanks so much for the great review:)

- Manager Response
Wonderful Stay
5/5 stars
Had a great time here. Definitely will stay again in the future. Very roomy, clean and conveniently located to the attractions. Thank you.
- Dorothy

Dorothy, We are so pleased to hear you enjoyed your stay at Orange Street Apartment. We hope you will come again soon! Thanks for the great review!

- Manager Response
Excellent Place
5/5 stars
Rental was very clean. It had all essentials needed for convenience. It was just 4 blocks from the shopping and tourism sites. Traffic was a little hectic, but expected seeing how it was a busy tourist area. Would rent there again, if in the area.
- Janet

Janet, We are so glad to hear you enjoyed your stay at Orange Street Apartment. We hope you will come again soon! Thanks so much for the great review:)

- Manager Response
St. Augustine Getaway
5/5 stars
Close to the historic district but we drove to the city garage to sight see. Lovely apartment. Very comfortable. Great for a quick getaway. One bathroom, 2 bedrooms. Nicely decorated. Great for 3 or 4 people. Would recommend this apt. Had no issues. Price was right!
- Sheryl

Sheryl, We are so glad to hear you had a 5 star stay at Orange Street Apartment. Thanks for being such great guests! We hope to host you again soon!

- Manager Response
Great Experience!
5/5 stars
Overall great experience! Clean, neat, and had everything you needed for your stay! Walking distance to everything so no need to drive. Communication was easy. We loved it!
- Jacob

Jacob, We are so glad you had a great experience at Orange Street Apartment. We hope to host you again soon! Thanks so much for the review:)

- Manager Response
Orange st
3/5 stars
Didn’t have any hand soap in the bathroom, floors were really dirty and there were only 2 bottles of water for 4 guest staying 2 nights. Also it’s above a real estate office so there’s no privacy during the week days if you want to hang out on the patio since it’s shared with the office below us. It would of been nice to know that we are right next to the busy highway which is very noisy when trying to go to sleep. Overall it was clean, had towels and gave us a place to sleep at night.
- Victoria

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Phone (800) 307-7117