Top 10% of guest reviews in this areaTop 10% of guest reviews in this area
1 bedroom1 bathroomSleeps 4
Popular amenities
Onsite parking available
Pet-friendly
Washing machine
Air-conditioning
Internet
Dryer
Rooms & beds
1 bedroom (sleeps 4)
1 bathroom
Bathroom 1
About this property
Winston at Ruby Dog on B Street
Winston, at Ruby Dog on B Street, is the ideal location for the traveling couple or the small family. This one bedroom / one bath pet friendly unit has beautiful views of the Atlantic Ocean from the large deck. The deck is on the east side of the building, which makes it a great spot to watch the sunrise in the morning and for a shady sea breeze retreat each afternoon with your favorite book. There is also a full size table on the deck, which is perfect for lunch after a long morning on the beach and for a romantic dinner under a starry sky.
The living room has plenty of room to spread out and relax. The large comfortable sofa can be used to sleep a third person if needed. Also, both the living room and bedroom have large flat screen tvs and high speed internet. The bedroom has a brand new queen size mattress and all new linens as well. Winston also has a twin size cot, which can be set up too. You’ll enjoy our completely remodeled bathroom that has a beautiful tiled walk-in shower. The kitchen features quartz countertops, new appliances, and has everything you’ll need to prepare, cook, and serve meals.
Ruby Dog on B is only one house off of the beach so access to the beach and ocean is just a few steps away. We provide beach towels and chairs for our guests to use during their stay with us. Also, we have an outdoor shower to rinse off the sand when returning from the beach. We have laundry area with a full size washer and dryer on site as well
Ruby Dog on B Street has a total of three separate units. Scarlett, Winston, and Cavalier Cottage can either be rented independently or in combination, depending on availability. Also within walking distance are several restaurants, shopping options, coffee shops, and miniature golf. The historic downtown area is an easy ten-minute drive north on A1A past the Lighthouse and over the Lions Bridge.
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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
Parties and events are allowed on site
Note from host: Please communicate prior to booking
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 and a deadlock
About the area
St. Augustine
St. Augustine is home to this apartment. St. George Street and St. Augustine Premium Outlets are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore St. Augustine Beach and Anastasia State Park. Looking to enjoy an event or a game while in town? See what's happening at Flagler College Tennis Center or Francis Field. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with ecotours and horse riding.
St. Johns County Ocean Pier - 20 min walk - 1.7 km
Anastasia State Park - 8 min drive - 5.8 km
St. George Street - 14 min drive - 9.4 km
Getting around
St. Augustine, FL (UST-Northeast Florida Regional) - 20 min drive
Restaurants
‪McDonald's - ‬4 min drive
‪Crabby's Beachside - ‬2 min drive
‪Starbucks - ‬3 min drive
‪Salt Life Food Shack - ‬2 min drive
‪World Famous Oasis Restaurant - ‬3 min drive
Frequently asked questions
Is Winston at Ruby Dog on B Street pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Winston at Ruby Dog on B Street?
As of 2 Jun, 2026, prices found for a 1-night stay for 2 adults at Winston at Ruby Dog on B Street on 29 Jun, 2026 start from S$383, 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 at Winston at Ruby Dog on B Street?
On-site parking is available at the property.
What time is check-in at Winston at Ruby Dog on B Street?
Check-in begins at 3:00 PM.
What time is check-out at Winston at Ruby Dog on B Street?
Checkout is at 10:00 AM.
Where is Winston at Ruby Dog on B Street located?
Situated in St. Augustine, this apartment building is within 1 mi (2 km) of Fiesta Falls Mini-Golf and St. Augustine Beach. Matanzas River and St. Johns County Ocean Pier are also within 2 miles (3 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
We had a wonderful stay! The rental was super clean and perfect for a couple’s getaway. Being right on the beach made it even more special—we absolutely loved it. Thank you for a great experience!
We always love staying here! Morgan is fantastic at communicating, the property is so cute and coastal-feeling, and the overall location can't be beat!
The Winston was great. Perfect location to walk to the beach and restaurants, and not a far drive to places around St. Augustine. Morgan was a great host, met us at check-in and responded quickly through the booking process. Would recommend staying here again.
Loved the cottage and location! Perfect to walk on the beach from and walk to some restaurants if choose to. Morgan was a great host. Would definitely recommend!
We absolutely loved the ease of the beach access, the coziness of the apartment, and communication with the renter was painless. Little tight spaces for a family of 4 but we made it work. Neighbors around us were so kind and friendly.
Tina H.
Stayed 4 nights in Jun 2025
About the host
Hosted by Morgan Nivens
Languages:
English
Premier Host
They consistently provide great experiences for their guests