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

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Fridge, microwave, oven, stovetop
Pool
Exterior
Fridge, microwave, oven, stovetop
Smart TV

Reviews

9.4 out of 10
Exceptional

Entire home

3 bedrooms3 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
    ‪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

Room options

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About the area

St. Augustine

This holiday home puts you in the heart of St. Augustine, within just a 10-minute stroll of Anastasia Island Mini-Golf and Tolomato River. Highlights at this holiday home include a kitchen, a private pool and a washing machine. .Home features free WiFi, 2.5 bathrooms and a balcony. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A sofa bed, a fenced private garden and a Smart TV are also available. .This pet-friendly holiday home offers a garden and barbecues. Plus you'll find laundry facilities. .Attractions within a 30-minute walk of this Davis Shores holiday home include Anastasia State Park and Flagler College.
View more Holiday homes in St. AugustineOpens in a new window

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

  • ‪Tradewinds Tropical Lounge - ‬3 min drive
  • ‪Harry's Seafood Bar Grille - ‬3 min drive
  • ‪Casa Reina - ‬3 min drive
  • ‪Conch House Restaurant - ‬12 min walk
  • ‪Candlelight South Restaurant - ‬16 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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.

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Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Car recommended
  • Onsite parking options include a garage

Kitchen

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

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city centre
  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping centre
  • 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

Policies

Check-in

Check-in time starts at 4:00 PM

Contactless check-in and check-out are 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 are welcome
  • Only dogs are allowed
  • Maximum 2 pets
    • Service animals are exempt from fees.

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
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
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. 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. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector and a first aid kit in all accommodation.

Property is also known as

Lion's Sail

Vrbo Property

Lion's Sail St Augustine

Lion's Sail St. Augustine

Lion's Sail Close to Downtown the Beach

Lion's Sail Ask About Our May Discounts!

Lion's Sail Private vacation home

Lion's Sail Private vacation home St. Augustine

Lion's Sail April Staycation Discounts for FL Residents!

Lion's Sail *April Staycation Discounts for FL Residents!*

107824

Frequently asked questions

Are there any beaches close to Lion’s Sail: Island Oasis w/ Pool near Downtown & Beach?

The closest beach to Lion’s Sail: Island Oasis w/ Pool near Downtown & Beach is Vilano Beach (4 km).

Does Lion’s Sail: Island Oasis w/ Pool near Downtown & Beach have a pool?

No, this holiday home doesn't have a pool.

Is there a private hot tub at Lion’s Sail: Island Oasis w/ Pool near Downtown & Beach?

No, but there is a private pool.

Is there a free airport shuttle available at Lion’s Sail: Island Oasis w/ Pool near Downtown & Beach?

No, Lion’s Sail: Island Oasis w/ Pool near Downtown & Beach does not offer an airport shuttle service.

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

Check-in begins at 4:00 PM. Check-out time is 11:00 AM.

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

Reviews

9.4

Exceptional

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

Reviews

10/10 Excellent

Linda T.

Liked: Cleanliness
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

10/10 Excellent

Peggy W., Minneapolis, MN

Liked: Cleanliness
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

8/10 Good

Bryan T.

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

6/10 Okay

Andre F.

Stayed 5 nights in Dec 2025

10/10 Excellent

Carly M.

Stayed 7 nights in Nov 2025

10/10 Excellent

Laura P.

Stayed 5 nights in Sep 2025

10/10 Excellent

Katie W., Elizabeth, Indiana

Liked: Cleanliness
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

8/10 Good

Michael L., Carrollton, VA, USA

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

Delita S., Leland, IL

Liked: Cleanliness

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.

Disliked: Cleanliness

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.

Liked: Cleanliness

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.

Liked: Cleanliness

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.

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

6/10 Okay

Steve L.

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

Christy W.

Liked: Cleanliness

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

Todd D.

Liked: Cleanliness

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

Dorie G.

Liked: Cleanliness

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

10/10 Excellent

Sandi F., St Petersburg

Liked: Cleanliness

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.

Liked: Cleanliness

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

Joey K.

Liked: Cleanliness

Great location

Great place, close to restaurants, shopping, beach.
Stayed 3 nights in Oct 2023

10/10 Excellent

Atheena W.

Liked: Cleanliness

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

10/10 Excellent

Stephen L.

Liked: Cleanliness

5 star

Very clean and well maintained property.
Stayed 7 nights in Aug 2023

10/10 Excellent

Verified traveller

Liked: Cleanliness

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

Brandon H.

Liked: Cleanliness

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

Liked: Cleanliness

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