Close to Castillo de San Marcos National Monument, Updated, dog-friendly gem w/fenced yard, foosball & pool tables, WiFi, fireplace provides amenities, such as golfing on-site and a garden. Stay connected with free in-room WiFi.
Professionally managed by Casago First Coast. Less than a mile from Historic Downtown St. Augustine, steps from Flagler College, and minutes from Castillo De San Marcos National Monument — this stunning dog-friendly home with a gas fireplace, fenced yard, and firepit is your perfect base for beaches, relaxation, and the magical Night of Lights.
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The Space
With the gorgeous sands of Vilano Beach two miles to the east and the charming Historic District of St. Augustine less than a mile to the south, Casa Di Fortune puts you right in the heart of everything this incredible city has to offer — without sacrificing space, comfort, or privacy.
This beautifully updated home sits on a large, tree-lined lot and is designed for groups who want room to spread out, gather together, and truly feel at home during their stay.
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The Layout
Inside, you will find a stylish, fully updated interior with hardwood floors, cool gray walls, and elegant furnishings throughout. The open-plan layout means the chef can work in the sleek, fully equipped kitchen while everyone gathers nearby — whether at the kitchen island barstools or around the adjacent dining table.
When it is time to relax, settle into the comfortable living room, light the gas fireplace on a cool evening, and enjoy the large TV or the in-home WiFi. Upstairs, a game room with a pool table and foosball table gives everyone another great space to unwind.
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Kitchen & Dining
The sleek, fully equipped kitchen has everything a group needs for home cooking — full-size refrigerator, stove and oven, microwave, dishwasher, blender, and coffee maker, plus all the cookware and dishes you need.
The kitchen island with barstools keeps everyone connected while meals are being prepared, and the adjacent dining table seats the whole group comfortably.
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Bedrooms & Sleeping Arrangements
This home comfortably sleeps up to 10 guests across four bedrooms.
Bedroom 1 — 1 King bed
Bedroom 2 — 1 King bed
Bedroom 3 — 1 Bunk Bed and 1 Single bed
Bedroom 4 — 1 Bunk Bed
The layout works perfectly for large families, multi-generational groups, or friends traveling together who need both privacy and plenty of shared space.
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Bathrooms
Bathroom 1 — Full bath with shower and toilet
Bathroom 2 — Full bath with shower and toilet
Bathroom 3 — Full bath with shower and toilet
Three private full bathrooms — no sharing required across the group.
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Outdoor Living
The outdoor spaces at this home are some of the best in St. Augustine.
Start your morning on the shady front porch with a coffee, taking in the tree-lined surroundings. Head to the spacious back deck — complete with a ceiling fan and a swinging papasan chair — for a more relaxed outdoor experience. As the evening comes around, gather the group at the firepit in the fenced backyard for drinks and great conversation under the Florida sky.
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Pets Welcome
Casa Di Fortune warmly welcomes your dogs. The large fenced yard gives them plenty of space to roam, play, and relax alongside you throughout your stay.
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In-Unit Amenities
• High-speed WiFi throughout • Large TV with standard cable and satellite • In-unit washer and dryer • Central air conditioning and ceiling fans • Gas fireplace • Pool table and foosball table — upstairs game room • Dedicated workspace • Fully equipped kitchen with dishwasher and blender • Garage with free parking for up to 4 vehicles • Carbon monoxide and smoke detectors • First aid kit and fire extinguisher
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Location & Nearby Attractions
Casa Di Fortune is perfectly positioned for exploring everything St. Augustine has to offer — less than a mile from Historic Downtown and just 2 miles from Vilano Beach.
• Historic Downtown St. Augustine — less than 1 mile south • Flagler College — steps away • Castillo De San Marcos National Monument — minutes away • Night of Lights — St. Augustine's beloved annual festival, right at your doorstep • Vilano Beach — 2 miles east • Fountain of Youth Archaeological Park — nearby • Trolley stop — 2 minute walk • Restaurants, cafes, boutiques, art galleries, and nightlife all within easy reach • Fort Mose Historic State Park — nearby for hiking and history
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Good to Know
• Check-in: 4:00 PM | Check-out: 10:00 AM • Maximum occupancy: 10 guests • Pets allowed — dogs welcome • No smoking anywhere on the property • Quiet hours apply — please respect neighbors • Free garage parking available for up to 4 vehicles
This property is professionally managed by Casago First Coast. Our team is available 24/7, 365 days a year. We are always just a message or a call away — we are here to make sure your stay with us is seamless from start to finish.
Property amenities
Internet
Available in the house: Free WiFi
Parking and transport
Onsite parking options include a garage
Kitchen
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Hob
Microwave
Oven
Refrigerator
Spices
Toaster
Bedrooms
4 bedrooms
Bedsheets provided
Bathroom
3 bathrooms
Hair dryer
Shower
Living spaces
Living room
Separate dining area
Entertainment
TV with cable/satellite channels
Outdoor areas
Balcony
Barbecue grill
Fenced yard
Garden
Laundry
Laundromat nearby
Washing machine
Work spaces
Desk
Desk chair
Comfort
Air conditioning
Heating
Pets
Pet friendly
Suitability/Accessibility
Smoke-free property
Services and conveniences
Iron/ironing board
Location highlights
Near a hospital
Near a zoo
Near an outlet shopping centre
Near the sea
Things to do
Billiards/pool table
Foosball table
Golf
Kayak
Basketball nearby
Birdwatching nearby
Casino nearby
Cycling nearby
Ecotours nearby
Fishing nearby
Golfing nearby
Hiking nearby
Hunting nearby
Jet skiing nearby
Kayaking nearby
Motor boating nearby
Parasailing nearby
Rafting nearby
Sailing nearby
Scuba diving nearby
Snorkelling nearby
Surfing/bodyboarding nearby
Swimming nearby
Theme park nearby
Water skiing nearby
Water tubing nearby
Wildlife walks nearby
Winery tours nearby
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
Pets are allowed
Service animals are welcome, and are exempt from fees
Children and extra beds
Children are welcome
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.
About the area
Located in Uptown, a neighbourhood in St. Augustine, this holiday home is near theme parks and by the sea. World Golf Village is a popular attraction and the area's natural beauty can be seen at Vilano Beach and St. Augustine Beach. Looking to enjoy an event or a game while in town? See what's going on at Francis Field, or consider a night out at Castle Otttis. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with hunting and hiking nearby. Visit our St. Augustine travel guide
Ponce de Leon's Fountain of Youth Archaeological Park
4 min walk - 0.4 km
Ripley's Believe It Or Not
14 min walk - 1.2 km
St. George Street
16 min walk - 1.4 km
Flagler College
3 min drive - 2.1 km
Castillo de San Marcos National Monument
5 min drive - 3.1 km
Getting around
St. Augustine, FL (UST-Northeast Florida Regional)
7 min drive
Restaurants
McDonald's
13 min walk
Bronx House Pizza
15 min walk
Ann O'Malleys
20 min walk
Village Inn
2 min drive
Castillo Craft Bar + Kitchen
17 min walk
Frequently asked questions
Is Updated, dog-friendly gem w/fenced yard, foosball & pool tables, WiFi, fireplace pet-friendly?
Yes, pets are allowed at this property.
How much is parking at Updated, dog-friendly gem w/fenced yard, foosball & pool tables, WiFi, fireplace?
On-site parking is available at the property.
What time is check-in at Updated, dog-friendly gem w/fenced yard, foosball & pool tables, WiFi, fireplace?
Check-in begins at 4:00 PM.
What time is check-out at Updated, dog-friendly gem w/fenced yard, foosball & pool tables, WiFi, fireplace?
Checkout is at 10:00 AM.
Where is Updated, dog-friendly gem w/fenced yard, foosball & pool tables, WiFi, fireplace located?
Located in Uptown, this holiday home is within 1 mile (2 km) of Old Jail Museum, St. George Street and Castillo de San Marcos National Monument. Davenport Park and Florida Heritage Museum are just steps away.
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All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
The property was perfect for the family. Everything was spotless and the check process was easy! Plenty of parking and at the end of a beautiful neighborhood. Would stay again!
This was such a great place to stay in St. Augustine. The house was laid out well and there was plenty of room for everyone. If you are going to stay in the historic district in St. Augustine this would be one place I would stay. We had everything there we needed it was close to the old jail and really everywhere in the historic district.
This place was perfect for our family! Lots of room and things to do just in the property itself. The pool table wasn’t accessible but the owners had reached out to us prior to let us know the previous renters broke it. The location is perfect! Would definitely come back!
Our stay at here was awesome! Great location, clean, had everything you would need and more. Communication was clear and instant. Would definitely stay here again!
I love this property it was clean and spacious and great for the kiddos with the playroom. We spent Thanksgiving weekend and had an amazing Friendsgiving getaway! We had our fur babies with us and they had plenty of room inside and outside.
The property was in a great neighborhood at the end of the street. Very well kept and maintained, had everything we needed to prep meals before heading out to explore. Will be staying again here on my next visit.
This is a nice place to stay at the only issue we had is when we got there we noticed a very bad smell upstairs in the bedroom and upon trying to locate the smell we found a dirty baby diaper in the dresser draw. So then we started checking house out and found a clear small baggy with residue in it in plain sight. The washer had a weird smell in it along with a bunch of candy wrappers. The floors needed to be cleaned better as well. You had to wear shoes or slippers the entire time or your feet would turn black from dirt. We did bring this up to the property management company and they offered to send someone out to clean but we did not want to wait around for the cleaning people or be there and wait around while they clean. So when we went to Publix we bought our own cleaner and wiped everything out. There is some general maintenance that needs to be completed on the property and landscaping taken better care of. If they get a different cleaning crew and do some fixes then the place would be back to what we remembered it. We stayed here a year ago and it was beautiful. Also replace the furniture that is comfy and clean.
Don’t stay here unless there are no other options.
Ok yall this is a weird place. The photos portray it as a nice stay but the house hasn’t been touched in years. The coffee table is gone, the rugs are stained and should have been thrown out 4 years ago. The towel racks that are installed are falling off the walls and the cabinets in the kitchen are broken and falling off. The walls haven’t been wiped probably since they opened this rental and the floor boards have never been wiped. The beds were very comfortable but the pillows should have been trashed last century. I agree with everyone else on the communication, it seems like I was talking to ChatGPT instead of a person when I voiced my commands and nothing was resolved or even reached back out. Upon arrival (mind you this is a family house) there were vape carts in the front lawn and the whole lawn is completely dead by the way, it’s just weeds and dust. The toilet seats when you pick them up have dried pee inside the seats. Overall if we could have stayed somewhere else that would have made this experience way better. It was very sad for our group because we were two families here for Mothers Day and I would reccomend to no one to stay here. Very unfortunate because the location is awesome.
Kalessin H.
Stayed 3 nights in May 2025
Verified
4/10 Poor
LeNard C.
5 Aug 2023
Liked: Check-in, listing accuracy
In my opinion
Do NOT stay here! The house looks beautiful online and a week before I went online to try and find some real-life photos and I was unsure if the photos of the house were photoshopped or not. When we arrived we immediately noticed the grass has not been cut for our arrival, which was a huge sign that the house was not ready although we waited until our listed check in time. Once we went into the house we noticed that the house was warm although the thermostat was set at 68 degree and currently showing 80 degrees inside.
As we began to settle in and put away our groceries we noticed there was a second trash can next to the sink that was completely full of trash left by someone else. There was a couple of highnoon alcoholic drinks and other trash but was completely full, clearly overlooked as the house was being prepped for our stay. During my walk through I noticed that the floors were dirty and as the evening went on we all noticed our shoes and socks were filthy from the floor.
After a few hours we noticed the AC was not changing the temperature so I called the number for Vacasa and within an hour an AC repairman was there. He fixed the frozen ac unit and water began to drip in the game room upstairs so the pool table was out of commission until we moved it and put the extra trash can that we emptied to real use to catch the water.
The next day we headed out to the beach and when we arrived back home the AC was again 80 degrees downstairs but 74 upstairs.
The air conditioning in the house was absolutely terrible! First night we found a bug crawling in the bed when checking the covers. There was no TV’s in any bedrooms so our kids were miserable when trying to go to sleep or relaxing from a day at the beach. Also the internet never worked.
We did everything trying to get the air to work. We flipped the breakers and it just kept blowing out hot air.
We tried to find the box to the internet to reset it. Never found it. The only TV’s in the house was the living room, but we couldn’t get the cable to work and the game room which was so hot!! On top of that there was no furniture in the game room to watch tv if you wanted to. There was tv mounts in all the bedrooms for some but no TV’s.
The bathrooms had no trash cans. No where to hang towels. Just wasn’t very convenient! The game room had an open plus with no covering. So a kid could put their hand in there and it electrocute them. We blocked it with a container but was still worried the kids would move it.
Also if you do decide to rent here don’t take a big vehicle. It’s SO hard to get in and out of the house. There was Always construction going on and we had to wait multiple times for them to move so we can get it. Even a smaller car would be a tight squeeze if you passed another vehicle.
We contacted VRBO to see what they could do and they kept saying they will get back with us. They offered to relocate us the next day but we didn’t hear back. It wasn’t until the 4th day when they said they “found us something” but it didn’t accommodate our party. Again never heard back. We have all the texted messages back and forth throughout the stay and it just wasn’t relaxing at all.
This is the most we had ever spent on a vacation home. We visit Florida 2-3 times a year and by far the worse experience. We would not rent here again unless things are updated and changed!