Vacation rentals with a pool in Anastasia Island

Fred & Linda’s place felt like we were right home. The place was very serene and tranquil right in the middle of St. Augustine. Anything we needed, it was there. The hosts also let us know that if we needed anything, to let them know. Their salt water pool felt great on hot afternoons and evenings. The kids loved the place. Even their little dog Ellie came to play ball with the kids. Would recommend staying here.

Monica’s house is truly spectacular! It looks just like the pictures - beautifully furnished, clean as a whistle, lots of light, and tons of space. She’s thought of all the little touches that make the place feel like home. We completely enjoyed the evenings by the pool and playing games around the dining table. The kids found the pool alligators and the PacMan arcade game to be highlights! Monica is a wonderful host and I wouldn’t hesitate to rent her place again! We feel lucky to have found it.

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!!!

So relaxing In such a beautiful setting. Loved relaxing in the sun by the pool. Able to get fresh eggs every morning from the hens on the property who were always excited to see us. Wouldn’t hesitate to visit again and stay at the property.

We had a wonderful stay! Lili’s precious home was comfortable, clean and in a great location. Only needed to contact her for recommendations and she was very quick to respond. We would absolutely stay here again and highly recommend!!

What a hidden treasure! I was looking for a getaway and what I found was a Haven. It surpassed all of my expectations. So peaceful, clean, and convenient. Close to everything yet tucked away into a quiet corner. Michelle is professional yet so friendly and helpful. Any questions you may have, she has the answer. Definitely one of my favorite places that I have ever stayed in the continental US. Five stars and two thumbs up!

A perfect spot for our family vacation! We loved the house, the pool area, and the proximity to the beach and St Augustine’s downtown.

Nicky was very responsive we were arriving early texted her and let her know she said it was ok if we went ahead and got to the house earlier than check in very helpfull she has a very pretty house a nice screened in pool and alot of good recommendations in a note book right in the house very well done we would definitely stay again

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!

Ashley's place was a pleasure to stay. Everything you need was available. Beautiful beach and close to several great restaurants.

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

My wife and I stayed at Kim's condo for our baby moon and we could not have enjoyed it more. Kim was a great host! We cannot wait to come back again. The condo was very clean and well stocked with everything we needed for our stay. We loved waking up each morning and going down to the beach to watch the sunrise and enjoy our coffee. We ate dinner on the balcony every night. This was probably our most relaxing trip we have ever been on. The condo was close enough to everything in St. Augustine, but far enough away from all the crowds. I would recommend this condo to anyone looking for a trip to St. Augustine. Without a doubt a 5 star experience and condo.

This was the cleanest rental we’ve ever stayed at. Seriously. I’m not just saying that. The sheets were so fresh smelling and clean. Cleanliness means A LOT to me when staying away for obvious reasons so that was the biggest positive. This condo has been beautifully updated and has everything you need. Like everything…all the kitchen items you need, laundry pods for clothes and towels, beach gear, etc. I didn’t even bring beach chairs because they had some and two of them were very nice. They have two bikes you can ride but we didn’t because we had our kids but that’s such a nice addition. It was so nice being so close to the beach and to so many great restaurants. The condo is also just a short drive from old town. This was exactly what we were looking for. Clean, quiet, close to the beach, close to seafood restaurants and close to old town. Oh! Also, the hosts are great! Very responsive, welcoming and helpful. We hope to rent here again!

Locating Windjammer was easy and directions into condo were great! Once there the accommodations were first rate. Very clean throughout and kitchen was well organized and well stocked. Bathroom towels all seemed new and toiletries, although small, were top notch. Beach equipment couldn't have been better, even lots of suntan lotion! All in all our experience in condo 107 was a superior experience. If we return to St. Augustine we will rebook!

It’s a nice cozy place within walkable distance to the beach. We had a great stay! I would definitely recommend this place.

Love staying at Chris’s places! This was our second stay, happened to be in a different unit. We will definitely try to go again! The view is awesome and the accommodations are perfect for us, simple and as described. Chris is a great communicator, very helpful and friendly.