Entire home

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

Holiday home with private pool, near Castillo de San Marcos National Monument

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.

Overview
Amenities
Policies
Location

Exceptional

3 bedrooms2+ bathroomsSleeps 121711.5 sq ft

Popular amenities

Parking available
Dryer
Air conditioning
Washer
Pool

Place, St. Augustine Lighthouse & Maritime Museum
Place, Flagler College
Place, St. George Street
Airport, St. Augustine, FL (UST-Northeast Florida Regional)

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

Amenities

Pool

Kitchen

Washing machine

Dryer

Pet-friendly

Free WiFi

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Pool
Kitchen
Washer
Dryer

House Rules

Check in after 4:00 PM

Minimum age to rent: 25

Check out before 11:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

Pets allowed: dogs (limit 2 total)

Smoking

Smoking is not permitted

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

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

About the area

St. Augustine

Located in Davis Shores, a neighbourhood in St. Augustine, this holiday home is near theme parks and near the beach. Shoppers can check out St. George Street, while everyone can enjoy the natural beauty of St. Augustine Beach and Vilano Beach. Looking to enjoy an event or a game while in town? See what's going on at Flagler College Tennis Center, or consider a night out at Castle Otttis. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

View more Holiday homes in St. Augustine

St. Augustine, FL

What's nearby

St. Augustine Lighthouse & Maritime Museum - 6 min walk - 0.5 km
St. Augustine Alligator Farm Zoological Park - 8 min walk - 0.7 km
Flagler College - 3 min drive - 2.4 km
St. George Street - 3 min drive - 2.7 km
Castillo de San Marcos National Monument - 3 min drive - 2.4 km

Getting around

St. Augustine, FL (UST-Northeast Florida Regional) - 20 min drive

Restaurants

‪Conch House Restaurant - ‬12 min walk
‪Mellow Mushroom - ‬8 min walk
‪Candlelight South Restaurant - ‬16 min walk
‪Circle K - ‬4 min walk
‪Mojo's Tacos - ‬4 min walk

Frequently asked questions

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

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

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 a 10-minute walk of Anastasia Island Mini-Golf, Tolomato River and St. Augustine Alligator Farm Zoological Park. Walker Charters and St. Augustine Lighthouse & Maritime Museum are also within 10 minutes.

9.4

Exceptional

9.2/10

Cleanliness

9.8/10

Check-in

9.4/10

Communication

9.8/10

Location

9.4/10

Listing accuracy

10/10 Excellent

Joey K.

16 Oct, 2023

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

Great location

Great place, close to restaurants, shopping, beach.

Stayed 3 nights in Oct 2023

8/10 Good

Michael L.

22 Jun, 2025

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

10/10 Excellent

Todd D.

21 Jun, 2024

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

10/10 Excellent

Atheena W.

17 Sept, 2023

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

8/10 Good

michael s.

1 Jan, 2022

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

Lions Sail

Very tastefully decorated and furnished. Was clean and appropriately stocked with everything in the kitchen you could need. We would stay there again. Only slight negative is it is a bit further from the city center than we thought.

Stayed 3 nights in Dec 2021

10/10 Excellent

Marlen G.

9 Apr, 2023

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

8/10 Good

William A.

16 Apr, 2023

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

As advertised

Property and service as described

Stayed 5 nights in Mar 2023

10/10 Excellent

Dorie G.

1 May, 2024

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

8/10 Good

Jennifer F.

14 Jun, 2023

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

10/10 Excellent

Verified traveller

7 Aug, 2023

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

10/10 Excellent

Jillianne G.

17 Jul, 2022

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

Loved Lions Sail

Booking property was very easy. Check-in was easy. We loved the decor, comfortablness and layout of home. The pool and fenced in backyard were huge bonuses for our family. Perfect area for our kids and dog. The location of Lions Sail is perfect for all the things we wanted to do. We will definitely be back. Biggest thing I would suggest is to put up some type of shade structure or retractable awning over the pool. After being in the sun all day at the beach, shopping, boating etc..., the last thing I wanted to do was come back to the house and get into the pool with my kids cause it was directly in the sun. I did it, but would've been nice to have an option for shade.

Stayed 5 nights in Jul 2022

6/10 Okay

Steve L.

25 Jul, 2024

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

10/10 Excellent

Katie W.

2 Aug, 2025

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

10/10 Excellent

Delita S.

22 Apr, 2025

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

2/10 Terrible

Patricia C.

12 Apr, 2025

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

10/10 Excellent

Kellie M.

8 Feb, 2025

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

10/10 Excellent

Jordan L.

6 Jan, 2025

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

8/10 Good

Christie T.

11 Dec, 2024

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

10/10 Excellent

Christy W.

7 Jul, 2024

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

10/10 Excellent

Sandi F.

18 Apr, 2024

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

10/10 Excellent

Sarah S.

15 Mar, 2024

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

10/10 Excellent

Stephen L.

26 Aug, 2023

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

5 star

Very clean and well maintained property.

Stayed 7 nights in Aug 2023

10/10 Excellent

Brandon H.

1 Aug, 2023

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

10/10 Excellent

RL B., Florida

27 Jul, 2023

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

10/10 Excellent

Kristen D., Loganville, GA

15 Jul, 2023

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