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

Saint Augustine, Florida
$351 avg/night Minimum Stay 3 Nights
Bed 3

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 12

Max Sleeps

Night 3 nights

Min Stay

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’rebordered 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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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    2 Total Pets Pet Friendly Welcoming Dogs Only
  • BEACH

    Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided Sofa Bed
  • GENERAL

    Unit Size: 1712 Sq Ft (159 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Oven Refrigerator Spices Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Car Recommended Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill Fenced Yard Garden
  • POOL/SPA

    Private Pool
  • BATHROOMS

    2.5 Bathrooms Hair Dryer Towels Provided
  • WORKSPACES

    Desk
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Birdwatching Nearby Marina Nearby Power Boating Nearby Theme Parks Nearby Whale Watching Nearby Wildlife And Game Walks Nearby Winery Tours Nearby
  • ENTERTAINMENT

    Smart TV
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    In The City Center Near A Health Or Beauty Spa Near A Hospital Near Outlet Shopping Near The Bay Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 12

Map Map

School District Availability

Review Review

  • Bryan T.

    Submitted Feb 20, 2026

    Stayed Feb 12, 2026

    Easy check-in and out. House was conveniently located to all of the sights we had mapped out, plus some!

  • Katie W.

    Submitted Aug 2, 2025

    Stayed Jul 17, 2025

    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!

  • Michael L.

    Submitted Jun 22, 2025

    Stayed Jun 14, 2025

    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.

  • Delita S.

    Submitted Apr 22, 2025

    Stayed Apr 18, 2025

    This home was super clean and accommodating. The bedrooms are really big and beds are comfortable. Kitchen is well appointed. Enjoyed our stay.

  • Patricia C.

    Submitted Apr 12, 2025

    Stayed Mar 30, 2025

    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.

  • Kellie M.

    Submitted Feb 8, 2025

    Stayed Jul 20, 2024

    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!

  • Jordan L.

    Submitted Jan 6, 2025

    Stayed Dec 22, 2024

    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.

  • Christie T.

    Submitted Dec 11, 2024

    Stayed Dec 2, 2024

    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.

  • Steve L.

    Submitted Jul 25, 2024

    Stayed Jul 8, 2024

    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.

  • Christy W.

    Submitted Jul 7, 2024

    Stayed Jul 2, 2024

    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.

  • Todd D.

    Submitted Jun 21, 2024

    Stayed Jun 18, 2024

    Property was very clean and modern. Location was great. Close to downtown and the beach.

Your dates are Available!

Total

Includes taxes and fees
$351+
View details