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!

We had a wonderful time. The cottage was clean and perfect for our stay. Lynne even left small gifts for our children as well as a gift card for the local restaurant. We could not have asked for a better host. Probably the best Airbnb experience we have had yet.

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!

Everything as described. Lovely place to stay. Really calm and peaceful.

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!

Great & very clean place! Near all attractions we wanted to go to and all the amenities inside the house were wonderful. Nice and very attentive host!

We had an absolutely wonderful stay at this Flagller Beach house! Everything about it was perfect—from the unbeatable location just steps from the beach to the beautifully maintained and comfortable property itself. The home was clean, thoughtfully stocked, and had everything we needed for a relaxing getaway. The host was incredible—welcoming, responsive, and went above and beyond to ensure we had a great experience. We truly enjoyed ourselves and would love to return. Highly recommend!

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!

Great host! And location was close to everything in St Augustine!

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.

We really enjoyed this gem! Fantastic location, comfortable, and felt like we had the best of all worlds here. We watched both the moonrise and sunrise on the beach, and had such a special time with our 3 kiddos. The beach chairs and boogie boards were an added bonus for us. Will definitely be back here and highly recommend!

Very cute and cozy place with everything we needed

We thoroughly enjoyed our stay in Jen’s home! Comfortable and charming! Loved the front porch and neighborhood peacocks. Walkable to restaurants and shops. Jen’s was super helpful and quick to respond to questions. Will definitely stay again!

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.

Quite literally a home away from home. Great interior/exterior and a quiet neighborhood. Streets are a little tight for a larger vehicle, but not a deal breaker. The house is conveniently located, so it was easy to get around the city, whether we drove or walked. Maite was lovely as well. Instructions were clear and concise, and responses were in a reasonable amount of time. Would definitely stay here again for another St.Augustine trip.

We loved our stay at the blue cottage - everything was immaculate with lots of thoughtful touches. The location was perfect for exploring St Augustine, everything was very walkable and there were some great coffee shops and cafes nearby. We also appreciated having parking on the property. Would highly recommend Stephanie’s place to anyone visiting St Augustine!

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!