Enjoy the charm of the nation’s oldest city from this stylish 2nd-floor retreat, just minutes from historic downtown and beaches. Relax in cozy living areas, a full kitchen, and a laid-back coastal vibe—perfect for couples, families, or solo travelers. Enjoy exclusive access to a private rooftop with panoramic views of the St. Augustine Lighthouse, Matanzas River, and historic district.
The space • HOME LAYOUT • 2 level (2nd and 3rd floor + Private Rooftop balcony) Holiday Home Living area, Kitchen, Dining Area, Bedrooms, Bathrooms
• BEDROOMS • The home has 2 bedrooms Bedroom 1 - Queen sized Bed (Sleeps 2 guests) Bedroom 2 - Queen sized Bed (Sleeps 2 guests)
• BATHROOMS • The home has a 2 full bathrooms, and are supplied with bath essentials (shampoo, body wash), towels, toilet paper, and a hairdryer.
• SHEETS/TOWELS • The home is professionally cleaned before every stay with clean linens and towels. Fresh new sheets, linens, and towels will be provided for your stay. We will prepare based on the number of guests.
Linens (sheet sets for bed) Blankets Bath Towels Washcloths Hand Towels
• KITCHEN & DINING • Indulge in the charm of this abode where culinary creativity meets dining delight. Nestled beside the dining room, the kitchen is a spacious haven for your gastronomic adventures. A quaint space with a dash of style, it boasts modern & stylish appliances ready to bring your culinary visions to life. The intimate proximity to the dining room invites a seamless flow from preparation to presentation, allowing the tantalizing aromas to enchant the senses as you embark on a culinary journey. This home beckons you to savor not just meals but moments, creating a symphony of flavors and memories in the heart of its vibrant kitchen.
• LIVING AREA • The home features a spacious and chic living room where comfort harmonizes with style. The generous layout encourages relaxation, adorned with plush seating, elegant decor, and an abundance of natural light cascading through expansive windows. This welcoming living area effortlessly links to the nearby dining space and kitchen The open design promotes a feeling of togetherness, facilitating effortless interaction among family and guests. Whether you're winding down after a day of activities or hosting friends, this living room offers a flexible and inviting atmosphere with convenient access to dining pleasures.
• LOCATION • St. Augustine, Florida, is nestled along the northeastern coast of the state, positioned approximately 40 miles south of Jacksonville. This historic city boasts a picturesque setting along the Matanzas Bay and the Atlantic Ocean. Renowned for its well-preserved Spanish colonial architecture, St. Augustine is the oldest continuously inhabited European-established settlement in the continental United States. The city's cobblestone streets wind through a charming historic district filled with landmarks, museums, and centuries-old structures. With its coastal beauty, rich history, and vibrant cultural scene, St. Augustine offers a unique and enchanting destination for visitors.
Historic & Cultural Sites Castillo de San Marcos – 4 min drive (1.4 miles) Historic District – 4 min drive (1.2 miles) Fountain of Youth Archaeological Park – 6 min drive (2.0 miles) Lightner Museum – 5 min drive (1.5 miles) Ximenez-Fatio House Museum – 5 min drive (1.4 miles) Lincolnville Museum & Cultural Center – 6 min drive (1.7 miles)
Family-Friendly Attractions St. Augustine Alligator Farm Zoological Park – 3 min drive (0.6 miles) St. Augustine Lighthouse & Maritime Museum – 3 min drive (0.7 miles) Whetstone Chocolate Factory – 5 min drive (1.7 miles) St. Augustine Distillery – 6 min drive (1.9 miles)
Beaches & Nature Anastasia State Park – 5 min drive (2.7 miles) St. Augustine Beach – 8 min drive (4.0 miles) Vilano Beach – 10 min drive (4.5 miles)
These are just a few highlights of the diverse attractions St. Augustine has to offer. Whether you're into arts and culture or outdoor activities, the "Old City" definitely has something for everyone.
• PARKING • Convenient parking is available in the driveway and along Arricola Avenue.
• OUTDOOR • Step outside into the backyard of this home, where a sprawling and verdant landscape unfolds, beckoning tranquility and leisure. Cozy accent chairs gather around a charming firepit, forming an intimate setting for conversations beneath the stars. A gently swaying hammock invites you to the perfect spot for serene relaxation amidst the natural surroundings. For moments of camaraderie and amusement, a strategically placed cornhole set awaits, encouraging friendly competition and shared laughter. This outdoor sanctuary effortlessly combines comfort, natural beauty, and entertainment, providing a versatile haven for both relaxation and recreation. Guest access During your stay, you will have the exclusive use of the entire home in the upper unit, ensuring privacy and comfort. The backyard however is shared with other guests from the lower level. Other things to note HOUSE RULES
• PETS: Pets (dogs/cats) are allowed for an additional fee of $50 per stay.
• CHECK-IN: Check-in time is after 4PM. Early check-in requests are subject to availability and cannot be guaranteed. If we’re able to accommodate an early check-in. Please check the availability of early check-in prior to booking.
• CHECK-OUT: Check-out time is before 10 AM. We do not allow late check-out as we schedule cleaning ahead of time. Any unauthorized late check-out will result in a charge of $50 for every 30 minutes.
• SMOKING: We do not allow smoking inside the property or in outdoor spaces including the balcony, backyard, and terrace (if applicable). There is a smoking fine of $500.
• NOISE: Please observe quiet hours after 9PM. Please be mindful of the neighbors as this property is situated in a quiet neighborhood. If the police are summoned due to noise complaints, this warrants a possible eviction with no refund.
• DAMAGES & LOSS: We would truly appreciate it if you could treat our home like yours. You will be responsible for any damages or loss to the property which will be charged to you as additional payment request or from your security deposit (if booked from other platforms). Please advise us of any damage or loss immediately upon discovery.
• UNAUTHORIZED GUESTS: Please make sure to book the property for the correct number of guests. Parties, events, or any kind of gathering are prohibited. No other guests outside the reservation are allowed on the property.
• PHOTOSHOOT/MUSIC VIDEOS: This property is for residential use only and not for commercial purposes without the written permission of the owner. Please contact us directly for booking of events.
• LOST AND FOUND: Please note that all shipping is at the traveler’s expense. There is a minimum $25 shipping cost plus a $50 service fee. We are not liable for any lost items. Our team will do our best to locate your lost items after check-out.
• MAILS & PACKAGES: We do not allow any mail deliveries or packages during your stay.
• ADDITIONAL NOTES ABOUT THE HOME
- Landscaper: A landscaper will be on property to maintain property grounds. They will not be accessing the home.
- Visits and Property Access: We will always notify in advanced should there be a need to access the homes and no one will ever enter without your approval. An exception is if there is a fire or life-threatening situations in the home.
Our prices include all fees. No hidden fees.
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Pets allowed: dogs and cats less than 50 lbs per pet (limit one pet total)
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Smoking
Smoking is not permitted
Check-out instructions
The host requires you complete the following before checking out:
Strip any used beds and gather used towels
Remove personal items and remove leftover food and drinks
Turn off the lights
Failure to complete these may result in a negative review from the host.
Important information
You need to know
Property # 4603409
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
Onsite parties or group events are strictly prohibited
Long-term renters welcome
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
About the neighborhood
St. Augustine
Located in St. Augustine, this vacation home is in the city center. Castillo de San Marcos National Monument is a notable landmark, and the area's natural beauty can be seen at Anastasia State Park and St. Augustine Beach. Ready for a night out? Consider The Conch House Restaurant and Dog Rose Brewing. Snorkeling, water skiing, and motor boating offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours nearby.
St. Augustine Lighthouse & Maritime Museum - 9 min walk - 0.8 km
St. Augustine Alligator Farm Zoological Park - 9 min walk - 0.8 km
Anastasia Island Mini-Golf - 11 min walk - 0.9 km
Anastasia State Park - 18 min walk - 1.6 km
Saint Augustine Amphitheatre - 3 min drive - 2.0 km
Getting around
St. Augustine, FL (UST-Northeast Florida Regional) - 26 min drive
Restaurants
Tradewinds Tropical Lounge - 4 min drive
Casa Reina - 4 min drive
Conch House Restaurant - 16 min walk
O'Steen's Seafood Restaurant - 15 min walk
Circle K - 9 min walk
Frequently asked questions
Is Anastasia Island Villa Upper Level + Rooftop pet-friendly?
Yes, this property allows cats and dogs (limit 1 total) with a maximum weight of up to 50 lbs per pet.
How much does it cost to stay at Anastasia Island Villa Upper Level + Rooftop?
As of Jun 20, 2026, prices found for a 1-night stay for 2 adults at Anastasia Island Villa Upper Level + Rooftop on Jun 21, 2026 start from $286, 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 Anastasia Island Villa Upper Level + Rooftop?
Check-in begins at 4:00 PM.
What time is check-out at Anastasia Island Villa Upper Level + Rooftop?
Check-out is at 10:00 AM.
Where is Anastasia Island Villa Upper Level + Rooftop located?
Located in Davis Shores, this vacation home is within 1 mi (2 km) of Matanzas River and Anastasia State Park. St. George Street is 1.9 mi (3 km) away.
Reviews
9.4
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Went ahead and gave this place a good review because overall it was thoughtfully put together and had a lot of charm. Communication was good, and the host was upfront about sharing the entrance with the downstairs unit. That part honestly did not affect the experience at all.That said, the biggest issue is definitely the furniture and beds. One full and one queen, and both the beds and sofa feel more staging-quality than meant for regular use. The rooftop view is absolutely dreamy, but getting there requires climbing a very steep attic ladder through a scuttle hole, so it’s definitely only for the brave.A few other things future guests should know:* Ask if the previous guest returned the fan remote because we couldn’t use the fan in the full bedroom.* There was a very strong air freshener smell when we arrived, and later the home had a strong spice aroma. Not bad, just noticeable.* Be gentle with the showerhead and downstairs barn door — both feel pretty fragile.One unadvertised bonus: they do have an EV charger, which was a huge plus.Overall, you can tell the renovation and furnishings were done creatively but on a serious budget. If the owner invested even a small amount into repairs and more comfortable furnishings, this place would honestly be a six-star stay. We would definitely stay again if the beds were upgraded.
Very clean and cozy villa. Everything was decorated so cute and the beds were super comfy. Close to everything and quiet neighborhood which is good for dogs that won’t go potty if there’s too much going on around them.