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

Photo gallery for Lion’s Sail: Island Oasis w/ Pool near Downtown & Beach

Cool off in the pool. Dip in and enjoy! Fully fenced for your privacy.
Clean and crisp. This kitchen is a pleasure to cook in!
Such a Great bedroom. Cheerful and bright.
Casual breakfast at the island bar. Whose up for Bloody Marys??
Maybe we will stay in and play today. What a gorgeous yard to enjoy.

Reviews

9.4 out of 10
Exceptional
3 bedrooms2+ bathroomsSleeps 12159 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Explore the area

View map
St. Augustine, FL
  • Place, St. Augustine Lighthouse & Maritime Museum
    ‪6 min walk‬
  • Place, St. Augustine Alligator Farm Zoological Park
    ‪8 min walk‬
  • Place, Anastasia State Park
    ‪17 min walk‬
  • Airport, St. Augustine, FL (UST-Northeast Florida Regional)
    ‪13 min drive‬

Rooms & beds

3 bedrooms (sleeps 12)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

2 Single Beds and 2 Double Beds

2 bathrooms, 1 half bathroom

Bathroom 1

Bathroom 2

Bathroom 3

Spaces

Kitchen
Balcony
Garden
Dining area

About this property

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

Welcome to Lion’s Sail — Your Peaceful Island Getaway between the Beaches and Historic Downtown St. Augustine

Nestled in the coveted Davis Shores neighborhood of St. Augustine, Lion’s Sail invites you to slow down, breathe deeply, and embrace island time.

This picturesque community—lined with towering oak trees, friendly neighbors, and meandering sidewalks perfect for evening strolls or bike rides—offers the best of both worlds.

You’re bordered by the Atlantic Ocean on one side and the Intracoastal Waterway on the other, with beautiful beaches and historic downtown just moments away.

Explore & Indulge:

Spend your mornings wandering centuries-old cobblestone streets, where horse-drawn carriages still echo the charm of days gone by.
Discover local art galleries, unique boutiques, and incredible restaurants, each one tempting you with delicious aromas drifting into the streets.

Relax & Reconnect:

When the day winds down, leave the bustle behind and return to your private oasis at Lion’s Sail.
Sip cocktails by the sparkling pool
Fire up the backyard barbecue
Or simply unwind beneath the oak canopy, letting the salty sea breeze wash your worries away.
Inside, the home is pristine yet cozy — open, light-filled, and designed for both comfort and calm.

The fenced backyard offers total privacy for lounging, playing, or cooling off in the cocktail pool.

Whether you’re here for adventure or relaxation, Lion’s Sail offers a slice of island paradise you’ll never forget.

Welcome home. Welcome to Lion’s Sail.

Pet Policy

We welcome up to two well-behaved dogs for a non-refundable fee:
$150 for one dog
$250 for two dogs
Please disclose pets upon booking so we can send the payment request.

A few friendly reminders:
No dogs in the pool — their fur clogs the filter.
Please clean up after your pets (a $500 fee applies if our cleaners must do so).
No other pets allowed.

Smoking prohibited anywhere on property.

Reservation holder must be present on property at all times any other members of group are present.

Reservation holder must be at least 25 years old- no exceptions!

Thank you for helping us keep Lion’s Sail beautiful, peaceful, and pet-friendly!
You must be at least 25 years of age in order to make a reservation. The person who makes the reservation must occupy the residence for the duration of the reservation.

Add dates for prices

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: dogs (limit 2 total)
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Smoking

Smoking is not permitted
You must be at least 25 years of age in order to make a reservation.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

We should mention

A car is recommended for transport to and from this property

Frequently asked questions

Is Lion’s Sail: Island Oasis w/ Pool near Downtown & Beach pet-friendly?

Yes, this property allows dogs (limit 2 total).

How much does it cost to stay at Lion’s Sail: Island Oasis w/ Pool near Downtown & Beach?

As of 27 March 2026, prices found for a 1-night stay for 2 adults at Lion’s Sail: Island Oasis w/ Pool near Downtown & Beach on 13 May 2026 start from NZ$522, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Lion’s Sail: Island Oasis w/ Pool near Downtown & Beach?

On-site parking is available at the property.

What time is check-in at Lion’s Sail: Island Oasis w/ Pool near Downtown & Beach?

Check-in begins at 4:00 PM.

What time is check-out at Lion’s Sail: Island Oasis w/ Pool near Downtown & Beach?

Checkout is at 11:00 AM.

Where is Lion’s Sail: Island Oasis w/ Pool near Downtown & Beach located?

Located in Davis Shores, this holiday home is within 1 mi (2 km) of Anastasia Island Mini-Golf and Anastasia State Park. Tolomato River and St. Augustine Alligator Farm Zoological Park are also within 10 minutes.

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 39 out of 50 reviews
Rating 8 - Good. 7 out of 50 reviews
Rating 6 - Okay. 2 out of 50 reviews
Rating 4 - Poor. 0 out of 50 reviews
Rating 2 - Terrible. 2 out of 50 reviews

9.0/10

Cleanliness

9.8/10

Check-in

9.6/10

Communication

9.8/10

Location

9.4/10

Listing accuracy

Reviews

Verified

8/10 Good

Bryan T.

Liked: Check-in, communication, location
Easy check-in and out. House was conveniently located to all of the sights we had mapped out, plus some!
Stayed 7 nights in Feb 2026
Verified

10/10 Excellent

Katie W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property and located exactly where we wanted to be! The pool was such a nice thing to have to keep the kids busy in between activities! I wish we would’ve had some way of cleaning the pool or someone to come clean it every couple of days. We used the skimmer the best we could but it really needed vacuuming. Overall a great experience and wonderful stay!
Stayed 5 nights in Jul 2025
Verified

8/10 Good

Michael L.

Liked: Check-in, communication, location, listing accuracy

Great location

We really enjoyed the stay overallOnly thing that was a bit annoying was the sheets in the guest rooms were not clean at check in and we had to wash before we went to bed the first night after 11 hour drive. Everything else was perfect.
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Delita S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cozy and Comfy

This home was super clean and accommodating. The bedrooms are really big and beds are comfortable. Kitchen is well appointed. Enjoyed our stay.
Stayed 4 nights in Apr 2025
Verified

2/10 Terrible

Patricia C.

Liked: Check-in, location
Disliked: Cleanliness, communication

House was just not clean

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 4 nights in Mar 2025
Verified

10/10 Excellent

Kellie M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place to relax

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 5 nights in Jul 2024
Verified

10/10 Excellent

Jordan L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house and location

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 4 nights in Dec 2024
Response from VrboOwner on 22 January 2025
Thanks for the great review! We're delighted you had such a wonderful time at Lion's Sail.We look forward to welcoming you back anytime!
Verified

8/10 Good

Christie T.

Liked: Communication, location

Holiday Getaway

A couple complaints. The couch wasn't clean and the floors had food on them. The website, sent through VRBO wasnt accessible. Thankfully, we havebvisited multiple times, so we knew what the town had to offer.
Stayed 4 nights in Dec 2024
Response from VrboOwner on 22 January 2025
Hello- we are sorry you had trouble accessing our guidebook link. Sometimes platform blocks it. However guidebook is just local recommendation, all easily found via internet search. All pertinent information for stay including door code, wifi info and house rules is sent in messaging thread. We would of been happy to answer any questions on recommendations through messaging thread as well, if needed :)
Verified

6/10 Okay

Steve L.

Liked: Check-in, communication, location

Round two stay.

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 6 nights in Jul 2024
Response from VrboOwner on 10 August 2024
Hi Steve- thanks for sharing your insight. We are a little confused why the lawn is mentioned when we had lawn service drop in during your stay. As we told you, the lawn is kept on a maintenance schedule of once a month.You first messaged two days into stay about the lawn on July 10th. Lawn service did a drop in outside of normal schedule on July 11th .We have shared feedback and urged homeowner to have them out once a week, but ultimately is up to them. Per our contracts we can not schedule services without approval.We believe taking stars off for something out of our property management company's hands is not fair. We received no correspondence on air filter or any cleaning concerns. The only message we received during your stay was about the lawn. Had we known we would have sent also maintenance over to replace filter.
Verified

10/10 Excellent

Christy W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Location

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 5 nights in Jul 2024
Verified

10/10 Excellent

Todd D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

St. Augustine stay

Property was very clean and modern. Location was great. Close to downtown and the beach.
Stayed 3 nights in Jun 2024
Response from VrboOwner on 6 July 2024
Thank you for your thoughtful feedback. Your perspectives are invaluable to us as we continuously work to refine our operations. Hope to welcome you back!
Verified

10/10 Excellent

Dorie G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Home

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 6 nights in Apr 2024
Response from VrboOwner on 27 May 2024
Your satisfaction is what drives us, and we can’t wait to welcome you back for another outstanding experience. Our check out procedures are very minimal and standard for industry. We apologize you found them to be cumbersome.
Verified

10/10 Excellent

Sandi F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Mini vacation for the Alligator Farm

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 3 nights in Apr 2024
Response from VrboOwner on 27 May 2024
Your satisfaction is what drives us, and we can’t wait to welcome you back for another outstanding experience.
Verified

10/10 Excellent

Sarah S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Senior Spring Break

We had our son and 7 of his friends stay here with us. Great location with lots to do.
Stayed 5 nights in Mar 2024
Response from VrboOwner on 10 April 2024
We’re really grateful and appreciate you taking the time to share your rating with us. Hope to host you again soon!
Verified

10/10 Excellent

Joey K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

Great place, close to restaurants, shopping, beach.
Stayed 3 nights in Oct 2023
Response from VrboOwner on 19 October 2023
We too love the houses closeness to shops, restaurant and the beach. We are so happy you had an enjoyable stay. Thank you for choosing The Proper Group.
Verified

10/10 Excellent

Atheena W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Such a great comfortable stay

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 3 nights in Sep 2023
Response from VrboOwner on 6 October 2023
Thanks so much for the review! We enjoyed hosting you and welcome you back anytime :)
Verified

10/10 Excellent

Stephen L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

5 star

Very clean and well maintained property.
Stayed 7 nights in Aug 2023
Response from VrboOwner on 15 September 2023
Thanks for the great review! We're delighted you had such a wonderful time. We look forward to welcoming you back anytime!
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Close to everything

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 4 nights in Aug 2023
Response from VrboOwner on 15 August 2023
Thanks for the great review! We're delighted you had such a wonderful time at Lion's Sail! We look forward to welcoming you back anytime!
Verified

10/10 Excellent

Brandon H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place close to Old Town

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 4 nights in Jul 2023
Response from VrboOwner on 11 August 2023
thanks for the great review! We're delighted you had such a wonderful time at Lion's Sail. We look forward to welcoming you back anytime!
Verified

10/10 Excellent

RL B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Summer 2023 family getaway

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 4 nights in Jul 2023
Response from VrboOwner on 15 September 2023
Thank you for your feedback on your recent stay at our Airbnb property. We value each of our guests and are happy to hear you enjoyed your visit.
Verified

10/10 Excellent

Kristen D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Rough start to the stay..great communication and resolution

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 6 nights in Jul 2023
Response from VrboOwner on 8 August 2023
We are sorry you experienced these issues during your stay but happy to hear we got everything addressed in a timely manner. Unfortunately damage happens as was the case with the TV being busted. of course the previous guests did not report they did this so we appreciate you bringing to our attention :)
Verified

8/10 Good

Jennifer F.

Liked: Check-in, communication, location, listing accuracy

Great location

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 5 nights in Jun 2023
Response from VrboOwner on 5 July 2023
Hi Jennifer -- thanks for the review and the helpful feedback. I wish you would have let us know about the pet hair and dirty floor -- we would have sent our cleaning crew out immediately to get that taken care of for you during your stay. The only issues you mentioned in the messaging were pool-related. We're available 24/7 for any issues guests have. We're sorry but we can't fix it if we're not made aware of the issue.
Verified

8/10 Good

William A.

Liked: Cleanliness, check-in, location, listing accuracy

As advertised

Property and service as described
Stayed 5 nights in Mar 2023
Response from VrboOwner on 8 August 2023
Were happy to hear you enjoyed your stay!
Verified

10/10 Excellent

Jennifer G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great property!!

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 3 nights in Apr 2023
Response from VrboOwner on 18 April 2023
Hi Jennifer -- We're so glad you had a great time at Lions Sail and that your kids enjoyed the pool! We look forward to seeing you again next time you visit the Nation's Oldest City. Thanks for choosing to stay with the Proper Group at Lions Sail.
Verified

10/10 Excellent

Marlen G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing!!

Everything was great!!! Can’t say anything negative because everything was as I expected!!!
Stayed 3 nights in Apr 2023
Response from VrboOwner on 18 April 2023
Hi Marlen -- we love it when we can meet our guests' expectations and it makes our day that we did just that for you. Thanks so much for choosing The Proper Group -- we look forward to seeing you again.

About the host

Hosted by The Proper Group Vacation Rentals

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