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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

Highlights

  • Family fun awaits
    Top rated for families.
  • Garage parking available
    Enjoy the convenience of garage parking - a rare offering in the area.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Close to Anastasia State Park
3 bedrooms2+ bathroomsSleeps 12

Popular amenities

  • Private pool
  • Garage parking available
  • Dog-friendly
  • Kitchen
  • Washer
  • Air conditioning

Explore the area

View in a map
St. Augustine, FL
  • Place, St. Augustine Lighthouse & Maritime Museum
    ‪7 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 Twin 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.
Our prices include all fees. No hidden fees.

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

Property # 1897690
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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated 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, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

About the neighborhood

St. Augustine

Located in Davis Shores, a neighborhood in St. Augustine, this vacation home is near theme parks and near the beach. Castillo de San Marcos National Monument and Ponce de León Hall are notable landmarks, and travelers looking to shop may want to visit St. George Street and St. Augustine Premium Outlets. 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. Spend some time exploring the area's activities, including wildlife walks, motor boating, and whale-watching.
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Map
St. Augustine, FL

What's nearby

  • Anastasia Island Mini-Golf - 6 min walk - 0.5 km
  • St. Augustine Lighthouse & Maritime Museum - 7 min walk - 0.7 km
  • St. Augustine Alligator Farm Zoological Park - 8 min walk - 0.7 km
  • Anastasia State Park - 17 min walk - 1.4 km
  • St. George Street - 3 min drive - 2.0 km

Getting around

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

Restaurants

  • ‪Harry's Seafood Bar Grille - ‬3 min drive
  • ‪Tradewinds Tropical Lounge - ‬3 min drive
  • ‪Casa Reina - ‬3 min drive
  • ‪Conch House Restaurant - ‬12 min walk
  • ‪O'Steen's Seafood Restaurant - ‬12 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).

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

As of Jun 7, 2026, prices found for a 1-night stay for 2 adults at Lion’s Sail: Island Oasis w/ Pool near Downtown & Beach on Oct 5, 2026 start from $352, 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?

Onsite 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?

Check-out is at 11:00 AM.

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

Located in Davis Shores, this vacation home is within 1 mi (2 km) of Anastasia Island Mini-Golf and Anastasia State Park. St. George Street is 1.8 mi (2.9 km) away.

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 41 out of 52 reviews
Rating 8 - Good. 7 out of 52 reviews
Rating 6 - Okay. 2 out of 52 reviews
Rating 4 - Poor. 0 out of 52 reviews
Rating 2 - Terrible. 2 out of 52 reviews

9.2/10

Cleanliness

9.8/10

Check-in

9.6/10

Communication

9.8/10

Location

9.4/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Linda T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
House was clean with plenty if room for our family. Backyard could use some TLC like mowing but we enjoyed our stay. Pool is small but refreshing.
Stayed 4 nights in Apr 2026
Response from VrboOwner on Apr 27, 2026
Thank you for your feedback! We’re so glad to hear the home was clean and spacious for your family and that you enjoyed your stay. We appreciate the note about the backyard and will be sure to share that with our team to keep everything looking its best. Happy to hear you still found the pool refreshing—it’s a great spot to cool off 😊 We’d love to host you again anytime!
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

Peggy W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a great place to stay! It was clean, well stocked, and a great location on Anastasia Island. Downtown is just minutes away. They even have plenty of pool towels. We were lucky the late March weather was warm and sunny for the pool. NOTE: The pool has NO heater, so if you're staying when temps are not 75, you may have cool swimming. You'll also need to empty the filter basket frequently so the pool can keep up with the trees debris. All in all highly recommend.
Stayed 3 nights in Mar 2026
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 Oct 19, 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

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 Jan 22, 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

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 Jul 6, 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

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

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 Aug 11, 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

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 Apr 10, 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

Mary Lou H.

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

great neighborhood

close to most attractions. great neighborhood to walk the dog and stretch legs.
Stayed 7 nights in Feb 2023
Response from VrboOwner on Aug 8, 2023
Thank you so much for taking the time to leave us a 5 star rating - it's much appreciated!
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

David G.

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

Great house, great location

Beautiful home, nice private yard and pool. Perfect location for beaches and town. Hosts responded immediately to our questions. Would 100% recommend to anyone looking for a great spot in the St Augustine area, and definitely hope to come back in the future.
Stayed 7 nights in Aug 2022
Response from VrboOwner on Sep 6, 2022
We so appreciate the feedback David and you're welcome back anytime!
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

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 May 27, 2024
Your satisfaction is what drives us, and we can’t wait to welcome you back for another outstanding experience.
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 Apr 18, 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

Verified traveler

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

Perfect stay in St Augustine/Anastasia!

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 3 nights in Jul 2022
Response from VrboOwner on Oct 20, 2022
Hi! We're so glad you had a great time at Lion's Sail. This is one of our favorite properties and you described why perfectly. We thank you for your great review and we look forward to hosting you again!
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 Sep 15, 2023
Thanks for the great review! We're delighted you had such a wonderful time. We look forward to welcoming you back anytime!
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

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 Oct 6, 2023
Thanks so much for the review! We enjoyed hosting you and welcome you back anytime :)
Verified

10/10 Excellent

Maria M.

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

House was fantastic

The house was great , beautifully decorated. We could see the lighthouse from the upstairs bedroom. The kids enjoyed it.
Stayed 5 nights in Jan 2023
Response from VrboOwner on Jan 31, 2023
Hi Maria -- thanks so much for letting us know you all had such a good time at Lion's Sail! We're glad we were able to meet your expectations and we thank you for choosing to stay with The Proper Group! We look forward to welcoming you back!
Verified

8/10 Good

michael s.

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
Response from VrboOwner on Jan 21, 2022
Thank you for taking the time to leave us a review. We are glad you enjoyed our property!
Verified

10/10 Excellent

Kevin S.

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

Great

Great
Stayed 1 night in Sep 2022
Response from VrboOwner on Oct 20, 2022
Hi Kevin --thanks for the positive review! We're so glad you had a great stay and we look forward to hosting you again.
Verified

10/10 Excellent

Mj D.

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

Accurate listing

Very comfortable
Stayed 6 nights in Oct 2022
Response from VrboOwner on Oct 14, 2022
Hi MJ! Thanks for the nice review! We couldn't agree more! We love the comfort and coziness of Lion's Sail. We look forward to hosting you again!
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 Apr 18, 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.
Verified

10/10 Excellent

Estuardo G.

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

Beautiful house and nice neighborhood

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 😫, but overall the house and location is excellent!
Stayed 3 nights in Dec 2022
Response from VrboOwner on Jan 20, 2023
Hi Estuardo -- we're sorry for any confusion regarding informing us about pets you're traveling with. Yes, we have to know as far in advance as possible if you're traveling with pets. We understand that things happen -- but we definitely need to know prior to your arrival at the vacation home. We're glad you enjoyed your stay and we thank you for choosing to stay with The Proper Group. We look forward to hosting you again.

About the host

Hosted by The Proper Group Vacation Rentals

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Languages:

English

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