Waterfront vacation rentals in Anastasia Island

The sunrises every morning from the deck were magical. The walk over the dunes to the beach, the morning coffee, the three bedrooms all made a perfect start to the day for me and my two sisters. We had an issue with a broken toaster which was addressed immediately. David was responsive and caring. For three adult women, the only thing that wasn’t ideal, but we knew it in advance, was the bedroom with bunk beds. They weren’t as comfortable as the two king size beds in the other two rooms, so someone has to make a sacrifice. But, all in all, we had a great time!

I made a mistake when choosing the dates for my trip, and didn’t realize till I showed up. I felt so silly, but reached out to Caio anyway, and he responded almost immediately even though it was late, and he was at an event out of state. He had had a cancellation and competently and graciously accommodate me last minute. I was so grateful! Check-in was easy, and our stay was super relaxed. We really enjoyed the easy access to the private beach. Would totally stay again!

This was our second stay at this lovely condo. The Unit looks exactly as advertised. Panoramic views of St. Augustine beach from a very well appointed condo. The kitchen is well stocked with high end glassware, knives, dishes etc. The living room has comfy couches and chairs. The king bed in the master suite is comfy with high quality linens. As this is an end unit there is a large balcony outside of the master suite overlooking the dunes and beach. In general, the Ocean Villas complex seems to be well maintained. The pool was kept clean and there was plenty of poolside seating and umbrellas. I'm sure we will book this unit again. Joan H

Exactly what we needed. Quiet, comfortable and so close to the ocean.

We had a great stay at Natalia’s cozy property! She and her husband were so accommodating and welcoming to us. The property is absolutely gorgeous, the dock is beautiful and the pool was amazing. You can tell how dedicated Natalia is to the landscaping, it’s beautiful! The apartment itself is very comfortable and the perfect size. It was also very clean! We really enjoyed our evenings and mornings out on the dock. The pool was fantastic and was my favorite part of our stay. The location is also amazing- Caps on the Water and Aunt Kate’s restaurants were both in walking distance and had amazing food! The beach is a short walk down the road and easily accessible. Downtown St. Augustine is just a short 10ish minute drive, and we loved staying in this quiet neighborhood but still having easy access to the downtown. We would definitely stay here again and thank Natalia and Steve for their welcoming hospitality! Thank you!!!

We really enjoyed our week stay and hope to return next year. Susan was a very responsive host and condo was comfy and nicely decorated with coastal decor. We especially loved the beautiful, private beach…well worth the walk!

Charming place in what looks like an up and coming part of town. Hosts were very responsive and helpful. Would definitely stay here again.

Was so easy to check in and get to the place. Didnt really need chat since the instructions were spelled out clearly. Everything was so clean and kept up. Been coming to St Augustine since 2012 and this was up there with one of the best places to stay!

Awesome place! Like new! We are always looking for newer places because we are very particular on cleanliness and this place made us feel right at home!

This home is a peaceful and scenic retreat, perfect for relaxation and reconnecting with nature. With stunning marsh views and plenty of space, my family felt completely at home. Though it’s about a 25-minute drive to downtown St. Augustine and the beaches, the tranquil surroundings make it well worth the trip—especially for those who love fishing, boating, or outdoor adventures. From paddleboarding and swinging on the swing to gathering around the fire pit and playing tag in the beautiful Florida weather, this place truly feels magical. Patricia is a wonderful host—always responsive and ensuring a comfortable stay. The cozy beds and well-equipped space exceeded our expectations, making it hard to say goodbye. We created unforgettable family memories here and can’t wait to return. Thank you, Patricia, for making our family reunion truly special!

We had a Wonderful Family vacation with our dogs here! The House was very clean, very close to the beach! The Kitchen very well stocked! Very Private and clean beach. Can't wait to return next year! Owner was also very responsive and helpful. Great great experience! Highly recommend for families and pets!

We had a great time and enjoyed the house. The host was very responsive. The views were beautiful. Historic St. Augustine is a quick drive away. There are other restaurants and ice cream places in walking distance. The house had everything we needed to cook and grill. I’m sure we will be going back again soon.

This was our second time booking for a family vacation and it was exactly what we wanted!! Beautiful, quiet, peaceful, relaxing environment. The guys loved fishing off the dock. The pool was just what we wanted and the fountain was fixed while we were there thanks to our AMAZING host. Very roomy home and always clean and freshly stocked with towels and linens. If your thinking about staying here I would absolutely recommend doing so. Pet friendly, with a doggy door on the patio. Great place for a girls get away, bachelorette, guys weekend, or a family get away. Host is very responsive to questions and concerns. We will be back!!!

We had a great stay here and will definitely be returning soon! The beach area was not crowded at all and the sand is nice and soft and great for kids. Plenty of restaurants close by and house has everything you need!

This is a really lovely place, and Elliott is a gracious and helpful host. We loved meeting Cat Dracula sleeping on the porch, and Elliott offered us many helpful suggestions for our visit and a parking space closer to town. The house is filled with beautiful artwork and interesting little curios, and being right on the water was great.

Had an amazing time! Wonderful home with amazing views and right on the water. He provided baby gates which helped with my toddler. Supplied beach chairs and umbrellas! Really great place to stay for families

I had an amazing stay at this condo! The view from the balcony was absolutely stunning—whether it was sunrise or sunset, the scenery made the experience unforgettable. It was the perfect spot to relax and unwind. The condo itself was spotless, stylish, and well-equipped with everything I needed for a comfortable stay. The bed was cozy, the kitchen had all the essentials, and the overall layout was spacious and inviting. The host was fantastic—very communicative, helpful, and made the check-in process smooth and simple. The location was also ideal, with easy access to local restaurants, shops, and attractions. If you’re looking for a beautiful, relaxing getaway with all the comforts of home and an unbeatable view, this is the place. I’ll definitely be coming back!

Jeremy’s place was everything we wanted! Incredibly clean, had everything we needed (even had snacks and a bottle of wine waiting for us after our 10 hour road trip). Incredibly easy access to a peaceful beach and tons of cards games and board games for downtime at the condo. He was responsive and very friendly to any and all questions we had. Definitely recommend and would stay again!

It was such a pleasure to stay in this condo. It is so close to everything. We will definitely go back and stay here.

Beautiful view of the beach and right next to the pool. We had a short stay but so glad we chose to stay here. Also highly recommend Commanders Outpost restaurant (3 minute drive down the street) for a great dinner

Rae's place is amazing. Exactly as listed. Location could not be ANY better...right on the sand and perfect distance to everything in the area. Highly recommend.

Great place to stay right on the beach. Beautiful beach view with direct access. Very clean & quiet retreat. We enjoyed our stay with our teenage daughter and niece. Will consider staying there again!

Wow! What a beautiful condo just steps from the beach with the most amazing views. The condo was super clean upon arrival, well stocked, and Terri is literally the best host ever! We have never seen anyone go above and beyond like she did! The decor is perfect, and we loved our time here. There is lots to do in downtown St. Augustine, or you can just relax at the beach. It was quiet and peaceful, and it’s a locked entrance to a private beach. The beach was never too crowded! We had the best time!

This is the perfect location for your trip. Beautiful and quiet beach right next to the condo. Beautiful ocean view. Only 15-20 min from downtown and a very easy drive. The condo is great and has everything you need. Would 1000% stay again