Cottage vacation rentals in Anastasia Island

Everything about this cottage was perfect! The location had a little trail right across the street to the beach. My mom and I stayed there for Mother’s Day week and LOVED everything about it. The hot tub was perfect! And the jasmine smell so good. Tamara was amazing with recommendations and communication!

Lynne’s home was perfect in every way. Every detail was thought of and accounted for. Comfiest beds I have ever stayed in on vacation. She was an incredible host. Extremely helpful and responsive. Cannot recommend enough or rate highly enough. Grateful for the opportunity to stay here.

Awesome little place, this was our honeymoon trip and we will definitely be back! Thanks again for everything

We had an enjoyable time in St. Augustine! Bryn Mawr, the beach & local restaurants are always amazing! We like riding our beach cruisers throughout the park & makes for a short ride to the beach or adult pool, the unit is very close to bigger pool which is also convenient! The unit had everything we needed & the front porch was perfectly shaded to have morning coffee! We would definitely stay there again, Stephen the owner is super accommodating!

This home was perfect for our family of 6. 15 minute walk (2 minute drive) to Malacompra Beach, which was extremely peaceful and not crowded whatsoever. This home was perfectly located between St. Augustine and Daytona Beach. The host was extremely responsive and friendly. As for the home itself, it was in a quiet area/neighborhood and everything in the home was very clean and organized. Highly highly recommend!

We loved our stay in Elizabeth’s cottage! The cottage is charming and cozy. The kitchen is well equipped with everything you could need.. Bedrooms are comfortable and supplied with lots of extra blankets and pillows. The cottage is perfectly located. It’s set back from the road. So, it is very quiet and is within a 10 minute walk to almost everything. Elizabeth is an amazing host! Very responsive and caring. This was a wonderful getaway for us!

We absolutely loved everything about our stay at this charming St. Augustine Airbnb! From the moment we arrived, the hosts made us feel welcome by personally introducing themselves—a thoughtful touch that set the tone for the rest of our stay. You can truly feel the love and care they’ve poured into this cozy rental. The location is perfect, with easy access to all that St. Augustine has to offer. The beds were incredibly comfortable, the shower felt luxurious, and the beautiful backyard with the firepit quickly became one of our favorite spots to unwind. Every detail has been so well thought out—it felt like a home away from home. If I could give it 6 stars, I would! We’re already looking forward to returning and can’t wait to book this lovely house again. Highly recommended!

This was a wonderful accommodation. The host was extremely proactive and provided useful recommendations, tips, etc. in their binder. Everyone else who lived in the community was extremely friendly and welcoming. It was a wonderful anniversary trip!

I had a great stay at Jocelyn and Jared’s cottage. The house itself was clean, cozy, and had everything I needed for a comfortable few days. One of my favorite parts was how dog-friendly the place is,my pup Ryu felt right at home, which made the stay even better. The only thing I’d mention is that the backyard and pool area could use a bit of attention. There was some yard debris, limited lighting at night, and an old shed that felt a little out of place. But other than that, everything inside the house was perfect, and I appreciated the peaceful atmosphere overall. Thanks again for hosting!

The perfect place to stay if you want to get downtown away from the busy town, but also be close by. The property is dreamy!

We truly enjoyed our stay and very much appreciated Deborah's attention to detail on the pre-arrival email letting us know exactly what we could expect the rental to include vs. what we would be responsible for so that we could plan ahead. Overall, the home and area is beautiful and very quiet. Would absolutely book here again!

This was mine and my husband’s first time staying in Florida and hands down loved this little home. Missy was amazing. The house was so cute! Was nice and quiet and wasn’t too bad of a drive from the places we wanted to visit.

My husband & I stayed at Rachel's place with our dog for a few days. Our stay was fabulous. The house is adorable & very comfortable. It had everything we could possibly need. Plus, it was in a wonderful location. We were close to everything. Our dog enjoyed the picket fenced yard & the sidewalks all around the neighborhood for walks. Rachel was very responsive any time I sent a message & always very nice. I would definitely stay here again & would have no problem recommending it to friends.

My girlfriend and I stayed here for her birthday and we absolutely loved it. The cottage by the castle was such a cool spot for a weekend getaway. Super cozy vibes, really unique views, and it felt like our own little hideout while still being close to everything. Definitely recommend if you’re looking to slow down and enjoy the scenery.

Very nice home. We were able to get to all our destinations in less than 10 minutes. Surrounding area was very quiet and in a nice neighborhood.

Beautifully renovated historic home with modern touches. The home is in the best spot for easy access to attractions, but far enough away to be quiet at night. Love the landscaping and all the wildlife it brought.

This is the 4th year we've stayed with Peter. All of his rentals are beautiful and centrally located to Vilano Beach (steps away) and to downtown St. Augustine. Peter is so quick to respond and helpful with any needs you may have. This year we brought friends and they raved about how excellent the space was as well. My husband's favorite detail is the bread and fruit provided as a welcome gift. We've been coming to vacation in St. Augustine for years and we wouldn't stay anywhere else!

We stayed at Phil's charming little place for a getaway weekend. It's a perfect location for the historic district. You'll never need your car because most everything is walkable. We felt very safe and it's in a quiet area. The cottage was very clean and had everything we needed. Phil made sure we were able to get in okay and was easy to reach if there was a problem. We would definitely stay here again. If you're looking for live music try Colonial Oak. If you want a great Italian dinner try Nonna's Trattoria. Both are within walking distance. Thank you Phil for providing the perfect oasis for a much needed relaxing weekend!

it would be hard to find a better place to stay in St. Augustine. walkable to everything!! the car could stay in the driveway the entire time. perfect for two couples. the set up allows a bit of privacy as the bedrooms are on separate floors. kitchen was great and the provided snacks and such were just perfect. Great hosts! will stay here again.

We loved the cottage from the moment we opened the door and plan on returning soon. It is in a great and quiet location in St Augustine a little north of the fort. Very walkable with some great little cafes nearby. The cottage is clean and bright and cozy at the same time. It is so clean that it looks like it has just been remodeled and painted! Furnishings are modern and comfy and the kitchen is awesome. We could not believe the number of thoughtful touches including snacks, water, coffee and awesome bath products that helped make our stay wonderful. I can’t forget to mention the welcome note and chocolates or the messages listing some recommended restaurants and sites in town. Stephanie really went above and beyond. It was the best AirBNB that we have ever stayed in….by far.

This was a beautiful, cozy home! Close to shops, restaurants, and sights of the city. Elaine was very kind and responsive. I felt reassured that if I needed anything, Elaine would be on top of it. Definitely recommend!