Lion’s Sail Island Oasis w/ Pool near Downtown & Beach

Great location, front porch view of the lighthouse.

Stayed: May 2025 Submitted: June 12, 2025

This home was super clean and accommodating. The bedrooms are really big and beds are comfortable. Kitchen is well appointed. Enjoyed our stay.

Stayed: April 2025 Submitted: April 22, 2025

Lovely home but very dirty. Ants all over counter near sink, nothing swept or vacuumed, Cheerios downstairs and upstairs floors and carpet. Furniture visibly dirty, couch pillows filthy, blankets in basket near couch full of holes. Sheets appeared to be clean but quilts very visibly filthy. Pool dirty when we arrived then mowed next day and when we arrived home pool covered with grass. I let them know and was told pool would clean Tues or Thurs and they came as we were leaving Thursday. Such a shame because the home itself was lovely.

Stayed: March 2025 Submitted: April 12, 2025

We loved our stay, amazing neighborhood, close to the amphitheater, the bridge of lions and more. Wouldn’t hesitate to stay here again!!

Stayed: April 2025 Submitted: April 10, 2025

Beautiful property just needs to pay for upkeep.

Stayed: March 2025 Submitted: March 24, 2025

We had an amazing stay at this house! The location was perfect—close to everything, making it easy to explore the area. The home was spotless and beautifully decorated with a charming nautical vibe that made it feel cozy and inviting. The pool was a fantastic bonus, providing a great place to relax and unwind. Highly recommend for anyone looking for a clean, convenient, and stylish getaway!

Stayed: July 2024 Submitted: February 08, 2025

The home was as pictured and clean with everything we'd need for a family stay. The location is perfect and close to old city St. Augustine.

Stayed: December 2024 Submitted: January 06, 2025

The Proper Group was accommodating and communicative. Our group enjoy how comfortable the space was and the walkable distance to our destinations was an added bonus. I would highly recommend this space and renting from The Proper Group in the future!

Stayed: November 2024 Submitted: December 08, 2024

The house was not worth the money. Positive: The location of property was awesome Negative: Ants in the kitchen Dirty swimming pool, paint or something got on our bathing suits Main shower was not cleaned, hair on shower floor Lawn maintenance came while we were in the pool and made us very uncomfortable staring at us

Stayed: September 2024 Submitted: September 20, 2024

Beautiful home and easy to live in. Is PERFECT for multi-generational travel!

Stayed: August 2024 Submitted: August 05, 2024

This is our second time at this property. Our first time was great it was well maintained and clean. This time not so much, the lawn was foot high and when I called the property manager they told they notified the owner but it was up to them. From a cleanliness perspective the place was fair. My wife has allergies so I checked the HVAC filter and it hadn’t been changed in a year so I replaced it myself. The place had a for sale sign out front so I assume the owner was more concerned with selling the property than continuing to rent.

Stayed: July 2024 Submitted: July 25, 2024

Very nice house with a lot of room for a big family. Awesome location close to downtown and the beach. Pool is very small however it works good for small children. Only negative was the yard was not mowed. Called first day and told them grass was high and no one ever called me back. Overall…great home and location.

Stayed: July 2024 Submitted: July 07, 2024

Property was very clean and modern. Location was great. Close to downtown and the beach.

Stayed: June 2024 Submitted: June 21, 2024

This was our second time staying at this home and we had an amazing time!! The space was perfect for our large group. the yard and pool were great for hanging out! It was spacious and clean. We will definitely be back again, and we recommend this home as the perfect place to stay with family and friends!

Stayed: May 2024 Submitted: June 14, 2024

Upon arriving entering was easy. House is Wonderfully clean, beautifully decorated, well stocked, Ready for us to relax. Everything was in order. Host was easy to communicate with. Beds are WONDERFUL, a Huge Bonus! I will add that the stairs are slippery, use with caution. We also had our two fur babies. The older could not manage his toenails on the stairs. No, problem, he stayed downstairs. Keep this place Proper, or the Host will threaten to charge you.

Stayed: April 2024 Submitted: May 01, 2024

Lovely home, with all the amenities of a home. Beautifully decorated and located within a few blocks of the Alligator farm and very close to historic parts of St. Augustine. Beds are comfortable! Would recommend to seniors, or families. Plenty of places to eat.

Stayed: April 2024 Submitted: April 18, 2024

place was good! a lot of things close by , specifically the beach!! definitely will return

Stayed: March 2024 Submitted: March 27, 2024

We had our son and 7 of his friends stay here with us. Great location with lots to do.

Stayed: March 2024 Submitted: March 15, 2024

Positive: The location is great. Right down the street from the downtown area. The place was so cozy and clean when we arrived. Things were provided like extra garbage bags, dishwasher detergent, laundry detergent and even makeup removing wipes. The house itself is adorable and nicely decorated. Beds are soft. The neighborhood is very quiet and safe as well. Overall it was a great stay and I would highly recommend!

Stayed: December 2023 Submitted: December 19, 2023

We recommend this property and will definitely consider another stay. Positive: The location was great. Easy access to downtown and the beaches. Walking distance to the Alligator Farm. Very nice neighborhood. Cozy house was well equipped with everything we needed during our 6 nights stay. Negative: Pool is very small. We came in November and were not using it but if you are planning on a summer trip do not expect to swim but rather a sit down party pool.

Stayed: November 2023 Submitted: October 22, 2023

Great place, close to restaurants, shopping, beach.

Stayed: October 2023 Submitted: October 16, 2023

The house is beautiful. The host was very responsive to help. Great location. Nice place to be with the family.

Stayed: September 2023 Submitted: October 03, 2023

This place did not disappoint! It was exactly as pictured online and was perfect for our entire family and pet. We couldn't have asked for a better stay. Communication with property manager was quick and timely. Everyone slept well and comfortably!

Stayed: September 2023 Submitted: September 17, 2023

We enjoyed our stay here.

Stayed: September 2023 Submitted: September 16, 2023

Very clean and well maintained property.

Stayed: August 2023 Submitted: August 26, 2023

This was our first visit to St Augustine so I knew nothing about the area. This property is close to everything. There’s an amazing taco place-Mojos Tacos within walking distance. It’s only 3 minutes from the alligator farm. We didn’t make it to the lighthouse but it’s so close you can see it from the house. As a woman traveling with teens, I felt safe in the neighborhood. The pool was surprisingly cool. I thought because it was smaller it would’ve been boiling hot but it was cool and refreshing. The historic area is only a 6 minute drive. Perfect location. House well maintained. Would def visit again.

Stayed: August 2023 Submitted: August 07, 2023

The property was very clean and maintained. A short trip to old town and all of St. Augustine's amenities. Will stay here again.

Stayed: July 2023 Submitted: August 01, 2023

We had some out of state family come down and meet us at St.Augustine for their first trip to our nations oldest city. Our families had the best time and this home certainly helped us to enjoy our time in St.Augustine. The neighborhood was quiet and peaceful and the home was so easy to find yet so close to anything we wanted to do. The home was comfortable for our group of 9 and well equipped from board games to kitchen utensils and anything you might need to enjoy some island time in St Auggie. The pool was perfect to cool off even though it was small our group had a great time enjoying the backyard amenities. Near dark you’ll definitely need to retreat inside as the insects were swarming and exposed skin, was their favored meal. All in all we had a wonderful time and great communication with our hosts throughout the process!

Stayed: July 2023 Submitted: July 27, 2023

Air was frozen and tv was busted. Filter didn’t look changed since the unit was installed. Serviced and worked perfectly. TV was replaced and the rest of the trip was excellent.

Stayed: July 2023 Submitted: July 15, 2023

Our stay in St Augustine was fantastic. The location was central to downtown and the beach and there were plenty of options within walking distance as well. The neighborhood was safe and quiet and we really enjoyed the large living room and private pool.There were a number of big thunderstorms while we were on our trip, one of which knocked out the power momentarily and tripped a fuse. The Proper Group team was very responsive and came by to fix everything immediately – even though it was not within typical working hours.We would definitely stay here again.

Stayed: June 2023 Submitted: June 29, 2023

House was in a really great location. Nice , newer house. Very comfy beds. Cons - floors were dirty - would catch dog hair when walking in socks. Bed linens had hair. Bed linens and wash cloths had stains. Master bath was tight and could not easily fit more than one person at a time. Pool does not have a cover so any rain or wind would blow debris into it and we would have to clean it out. Overall, nice place just needs better cleaning.

Stayed: June 2023 Submitted: June 14, 2023

Fantastic space for a group of friends to get together and enjoy time with each other! Very clean and spacious. Many great restaurants close by. The host did a knock out job with this listing.

Stayed: April 2023 Submitted: April 23, 2023

Property and service as described

Stayed: March 2023 Submitted: April 16, 2023

We really enjoyed our stay at Lions Sail! We had plenty of room for our family of 5. Our kids loved the pool. Perfect location with a short drive to downtown or the beach. When back in St. Augustine we will definitely consider this property.

Stayed: April 2023 Submitted: April 12, 2023

Everything was great!!! Can’t say anything negative because everything was as I expected!!!

Stayed: April 2023 Submitted: April 09, 2023

My business partner and I decided to have a meeting and bring our families along. The house was great, we had ample room and were able to bring our dog as well. Place was comfortable enough to have my family and my business partner”s family over for pizza and conversation.Proximity to all of the sites was great, Less than 4 miles to most areas we wanted to see such as the fort, the lighthouse, the beach and old downtown. Would stay again in the future.

Stayed: March 2023 Submitted: March 19, 2023

My friends and I loved this property! It was only 6-8 minutes away from the beach and was a great getaway after a long day in the heat. The backyard pool was refreshing and the hosts were super respondent when we had issues with the microwave. The bunk beds were nicer than expected and actually super spacious. The only thing I would comment on is the wifi; we had some issues with connectivity but otherwise, this stay was great! I would definitely stay here again :)

Stayed: March 2023 Submitted: March 09, 2023

close to most attractions. great neighborhood to walk the dog and stretch legs.

Stayed: February 2023 Submitted: March 06, 2023

The house was great , beautifully decorated. We could see the lighthouse from the upstairs bedroom. The kids enjoyed it.

Stayed: January 2023 Submitted: January 07, 2023

We really enjoyed the house, nice and clean and well equipped specially the kitchen, nice patio, and we liked that it was pet friendly, just make sure you informed the property manager at the moment of the reservation about the pets you are taking because if you don’t do it on time they will charge you double the pet fee, that was our case

Stayed: December 2022 Submitted: January 01, 2023

Great place and safe neighborhood. Plenty of space and well organized. We walked everywhere and only got in our car once to head south to the beach area for dinner one night. 4 days to explore was all we needed to enjoy all St Augustine had to offer. Fun town.

Stayed: December 2022 Submitted: December 06, 2022

Great place to stay, very clean and plenty of room. Also close to St Augustine and all attractions.

Stayed: November 2022 Submitted: November 26, 2022

Perfect location and perfect place to bring a family. It's was just us a and our pup but was great to have the whole place to ourselves. Seeing the lighthouse at night from the front porch was pretty great. Local area is full of so many things to do. Close to it all but not too close.

Stayed: October 2022 Submitted: October 27, 2022

Very comfortable

Stayed: October 2022 Submitted: October 13, 2022

We absolutely loved our stay at the Lion's Sail. The home is beautifully furnished with everything we needed (from linens to kitchenware), making it a great home away from home for our family of 10. Plus it was convientely located 7 minutes away from our downtown wedding. Would definitely stay there again.

Stayed: September 2022 Submitted: September 25, 2022

House was well stocked and clean. Cute decor. Comfortable. A few suggestions to make it better. Horrible mattress pads on king bed too soft! Need luggage stand in king bedroom, some sort of mosquito control when out by pool. Also how about beach chairs that can be borrowed.? Ours broke first day and we were going to spend buy one at the inflated prices in town.

Stayed: August 2022 Submitted: August 30, 2022

This place is great! The house is super clean, spacious but cozy, and equally convenient to Old Town, St Augustine Beach, and most of the central attractions. The kitchen was very well equipped with good quality tools and things. The pool is definitely small but still very relaxing and big enough for 4 or 5 adults to hang out in. The house is close to A1A but we didn’t hear any traffic noise. The street itself is very quiet and there are speed bumps to control traffic through the area. Definitely recommend this property but the management was amazing. They were extremely accommodating to us and they were responsive and attentive while we were there. They really made it great!

Stayed: August 2022 Submitted: August 22, 2022

We had a wonderful family reunion, vacation at Lion’s Sail. The location is great with quick access to downtown St Augustine, Anastasia State Park and the lighthouse. The house was clean, cozy and well-equipped. The backyard was lovely and we enjoyed relaxing there. I highly recommend this property.

Stayed: July 2022 Submitted: August 03, 2022

This home is in a perfect location, close to downtown and the beach. Our kids loved the pool and our family of 6 had plenty of room to spread out. Very easy check in and check out process! We would definitely recommend this place to others.

Stayed: July 2022 Submitted: July 30, 2022

Our group had a wonderful stay and the house was perfect! We had a group of 12 and the house was spacious and accommodated us super well. We will definitely be coming back and highly recommend this place to anyone!

Stayed: May 2022 Submitted: June 05, 2022

AC great. Extra blankets were great. Sheets and decorations are lovely. The specific check out list was extreme in comparison to price of house. Pretty pricey house. House is easy to find in an older neighborhood. Good location, but not close to the beach. Plenty of extra linens, Toilet paper, dishes & kitchen items, big frig, small pool in the backyard.

Stayed: April 2022 Submitted: May 11, 2022