Apartment

Winston at Ruby Dog on B Street

Apartment in St. Augustine, steps from St. Augustine Beach

Photo gallery for Winston at Ruby Dog on B Street

Living area
Living area
Living area
Interior
Living area

Reviews

10 out of 10
Exceptional
1 bedroom1 bathroomSleeps 4

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Air conditioning
  • Ocean view

Explore the area

View map
  • Place, St. Augustine Beach
  • Place, St. Johns County Ocean Pier
  • Place, Anastasia State Park
  • Airport, St. Augustine, FL (UST-Northeast Florida Regional)

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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Amenities

Washing machine
Dryer
Pet-friendly
Air conditioning
Ocean view
Parking available

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House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

Events allowed
Please communicate prior to booking
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Pets

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

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. Castillo de San Marcos National Monument is a notable landmark, and the area's natural beauty can be seen at St. Augustine Beach and Vilano Beach. Fiesta Falls Mini-Golf and St. Augustine Alligator Farm Zoological Park are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
St Augustine Beach, FL

What's nearby

  • St. Augustine Beach - 1 min walk - 0.0 km
  • St. Johns County Ocean Pier - 20 min walk - 1.7 km
  • Butler Beach - 3 min drive - 3.4 km
  • Anastasia State Park - 5 min drive - 5.8 km
  • St. George Street - 9 min drive - 10.1 km

Getting around

  • St. Augustine, FL (UST-Northeast Florida Regional) - 20 min drive

Restaurants

  • ‪Circle K - ‬2 min drive
  • ‪Crabby's Beachside - ‬2 min drive
  • ‪Salt Life Food Shack - ‬2 min drive
  • ‪Beachcomber - ‬4 min walk
  • ‪Circle K - ‬2 min drive

Frequently asked questions

Is Winston at Ruby Dog on B Street pet-friendly?

Yes, pets are allowed at this 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. St. Johns County Ocean Pier and Matanzas River are also within 1 mile (2 km).

Reviews

10

Exceptional

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy
Rating 10 - Excellent. 176 out of 183 reviews
Rating 8 - Good. 5 out of 183 reviews
Rating 6 - Okay. 2 out of 183 reviews
Rating 4 - Poor. 0 out of 183 reviews
Rating 2 - Terrible. 0 out of 183 reviews

Reviews

10/10 Excellent

Alexis W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a great place to stay, excellent location from the beach and it is super dog friendly. Overall its a great place
Stayed 4 nights in Sep 2025

10/10 Excellent

Erinn L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 7 nights in Sep 2025

10/10 Excellent

Melody B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Our short stay

Had a great time ..Morgan was so helpful he was great i would recommend this place to everyone
Stayed 3 nights in Jul 2025

8/10 Good

John P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cozy Retreat

We had a good time at the property.It was nicely decorated . We enjoyed a nice view from the balcony and closeness to the beach.
Stayed 7 nights in Mar 2025

10/10 Excellent

Willow K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Rustic Beach Stay !

Perfect size for my husband and I. Amazing beach access and great location in town. We will definitely be visiting again!
Stayed 3 nights in Jun 2024

10/10 Excellent

Margot M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Beach Getaway

Couldn’t have asked for a better spot close to the beach! Check in was seamless and we had everything we needed for the weekend! Plus the apartment was incredibly clean! Thank you Morgan & team!!
Stayed 3 nights in May 2025

10/10 Excellent

Donna L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Birthday Celebration

We loved it and will definitely stay there again!
Stayed 4 nights in Oct 2024

10/10 Excellent

Cydney G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect beachside getaway

Property host was so helpful and very responsive to any questions we had about the area. Would definitely stay there again!
Stayed 3 nights in Jan 2023

10/10 Excellent

Jean E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Ocean Gem

Always our favorite spot!
Stayed 5 nights in Mar 2025

10/10 Excellent

Tracy N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect little apartment

We absolutely loved our stay at Winston! The apartment was beautifully decorated, clean and roomy for the two of us with a lovely view from the deck. The street was quiet and we were able to walk to several restaurants. We’ve been to St. Augustine many times and this was one of our favorite stays.
Stayed 4 nights in Feb 2025

10/10 Excellent

Magda H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

Very nice stay! We will be back
Stayed 3 nights in Jul 2022

10/10 Excellent

Paul M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place!

We loved the bungalow feel and the location. Close to everything the area has to offer. The property manager was excellent and helpful. The unit was totally outfitted -can’t think of a thing we needed to get except food.
Stayed 3 nights in Aug 2024

10/10 Excellent

Michael C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Beach Stay

Just a fantastic place for a beach holiday. Location and beach are great, and the apartment is absolutely perfect. Morgan was there to greet us on check in, answered any questions we had. Couldn't ask for a better stay in St Augustine.
Stayed 5 nights in Aug 2023

10/10 Excellent

Nancy F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful

We had a wonderful time staying here! The apartment was just perfect for us, very clean and quiet! Morgan was there to greet us and he was very helpful and a pleasure to deal with! We will definitely return!
Stayed 4 nights in Dec 2022

10/10 Excellent

David R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

2 Week Summer Getaway!

Great little apartment 2 houses from the beach! My wife and I really enjoyed our time at the beach apartment. We brought our 80lb Akita with us and she absolutely loved it! We’ll definitely look to rebook next year.
Stayed 14 nights in Jun 2024

10/10 Excellent

Erinn L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

We keep coming back

Love staying at Ruby Dog! This was our first stay over the inter and it was just as enjoyable as the other times. So many great food and drink options within walking distance and easy access to tons of attractions and downtown. The place is always clean and ready when we arrive, and we're always sad to leave when it's time to go.
Stayed 3 nights in Jan 2023

10/10 Excellent

Anna C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Winston :)

We loved our stay at Winston! The space is so cute and makes you feel right at home. Fast and easy communication with the owner. The location is great and walking distance to the beach. Perfect for a small family. Will definitely look into staying in these properties again next trip back.
Stayed 3 nights in Jun 2023

10/10 Excellent

Alyssa C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful stay

Loved the place and the location, Morgan was very polite and welcoming at check in. Our dogs were also welcome and had a great time. The place has beach towels and chairs and a wagon for your use. The outdoor shower didn’t work but we didn’t mind using the hose to clean off. Would definitely stay at the place again. Truly a gem.
Stayed 6 nights in Jun 2023

10/10 Excellent

Erinn L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

We love it!

We've never stayed at the same place twice when vacationing, that is, until we came here. This was our fourth stay at Ruby Dog on B. It feels like a home away from home. Morgan is great to work with and is very responsive. The space itself is decorated really cute and feels nice and spacious. There are tons of great places to eat and drink within walking distance, and it's just a short drive to downtown.
Stayed 8 nights in Sep 2023

10/10 Excellent

Haiden N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Place!

This was just a cute little apartment steps from the beach! It was very clean, unique, and very close to everything! Several restaurants within walking distance, quick ride to historic downtown, and DOG FRIENDLY! Morgan the host was just simply amazing! We got in super late because we were driving with a baby, so we opted to drive while he slept. Morgan checked in on us several times to make sure we made it ok, and he left all the lights on for us so we didn’t have to unload in the dark. Everything was great. I’d stay there or in any of Morgan’s properties again!
Stayed 4 nights in Aug 2023

10/10 Excellent

Herbert P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place, by the beach for a couple

Great little place for 2 adults and a dog. The place was in immaculate condition. It was clean and the shower, was one of the largest we have had since staying in houses by the beach. Everything you needed was provided, even chair and wagons to carry them to the beach. The host Morgan was outstanding, he couldn't do enough to help us settle in and answer all our questions. As we were traveling from out of state, even allowed us to check in a little early. I would highly recommend this place to family and friends. We really enjoyed our stay. Also, there were a few good restaurant and bars closed by, for those who prefer to eat out. Once again thanks Morgan for your assistance, hopefully we'll see you again.
Stayed 5 nights in May 2023

10/10 Excellent

Makayla H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Could not have picked a better place to stay with our dog. Such a cute place and an amazing location! We will definitely be back!
Stayed 4 nights in Sep 2025

10/10 Excellent

Deborah M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Pet friendly close to beach cute decorating
Stayed 5 nights in Sep 2025

10/10 Excellent

Cal W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Aug 2025

10/10 Excellent

Juliene B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

The Ruby Dog is the real deal

We absolutely love the Ruby Dog on B Street. It is one of our absolute favorite places and every year it just gets better and better. There is really no other option to us than staying with Morgan. The Winston is the perfect home away from home, that we're also able to bring our dog with us. On top of Morgan's hospitality, it's truly unbeatable.
Stayed 5 nights in Jul 2025

About the host

Hosted by Morgan Nivens

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests