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

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Fridge, microwave, oven, stovetop - Lion’s Sail: Island Oasis w/ Pool near Downtown & Beach (St. Augustine)
Exterior - Lion’s Sail: Island Oasis w/ Pool near Downtown & Beach (St. Augustine)
3 bedrooms, desk, iron/ironing board, free WiFi - Lion’s Sail: Island Oasis w/ Pool near Downtown & Beach (St. Augustine)
Smart TV - Lion’s Sail: Island Oasis w/ Pool near Downtown & Beach (St. Augustine)
Pool - Lion’s Sail: Island Oasis w/ Pool near Downtown & Beach (St. Augustine)
In the charming Davis Shores neighborhood, Lion's Sail offers a serene retreat. Take a leisurely bike ride to State Park Beaches or unwind by the pool with cocktails and barbecue in the backyard. Fresh salty air still lingers as beach breezes blow past this zen space.

Reviews

9.4 out of 10
Exceptional

Entire home

3 bedrooms3 bathroomsSleeps 12159 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi

Add dates for prices

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.

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Car recommended
  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 2.5 bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • Smart TV

Outdoor areas

  • Balcony
  • Barbecue grill
  • Fenced yard
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center
  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping mall
  • Near the bay
  • Near the marina
  • Near the sea

Things to do

  • Birdwatching nearby
  • Motor boating nearby
  • Theme park nearby
  • Whale watching nearby
  • Wildlife walks nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher

General

  • Garden
  • Unit size: 1,712 square feet

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Exterior
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  • Kitchen
  • Washer
  • Dryer
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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Rules

You must be at least 25 years of age in order to make a reservation.

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total pets

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

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
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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

A car is recommended for transportation 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 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. Tolomato River and St. Augustine Alligator Farm Zoological Park are also within 10 minutes.

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Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens 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

Cleanliness

9.8

Location

Reviews

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
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
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
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
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
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

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
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
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
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

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
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
Verified

10/10 Excellent

Verified traveler

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
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
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

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

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
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

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
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
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
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

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
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
Verified

10/10 Excellent

Kevin S.

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

Great

Great
Stayed 1 night in Sep 2022