Waterfront~Sleeps 12~4BD 2.5BA~Pet Friendly~Kayaks~Boats Welcome~On the Bay

Santa Rosa Beach, Florida
$458 avg/night Minimum Stay 2 Nights
Bed 4

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 8

Max Sleeps

Night 2 nights

Min Stay

Bailey’s Bayside on Buck Bayou — Private Waterfront Escape

Welcome to Bailey’s Bayside, a private 4-bedroom, 2.5-bath waterfront retreat tucked away in a quiet residential pocket of Santa Rosa Beach. Located directly on Buck Bayou with quick access to Choctawhatchee Bay, this home offers the perfect balance of peaceful waterfront living and easy access to Crab Island, The Bay Restaurant, Sandestin, Grand Boulevard, 30A, and Destin’s world-famous beaches.

Bring your boat, your fishing rods, and even your pup — this is coastal living done right.

Why Guests Love Bailey’s Bayside

• Waterfront property on Buck Bayou
• Bring your boat (water depth may be lower in winter months)
• Boat trailer parking
• Private dock for fishing, swimming, and possible boat tie-up (size dependent)
• Kayaks provided
• Large backyard and partially covered porch
• Pet friendly
• Private home in a quiet neighborhood
• Beach towels provided
• Close to Sandestin and Grand Boulevard
• Complimentary Free Fun Package included

Whether you’re heading out to Crab Island, cruising to waterfront dining, or simply enjoying sunset views from the dock, Bailey’s Bayside offers a slower, more peaceful side of the Emerald Coast.

Home Layout

First Floor
• Fully equipped kitchen
• Dining room with seating for six
• Laundry room with full-size washer and dryer
• Half bath
• King bedroom with water view

Second Floor
• Primary bedroom with king bed, water view, and private bath (tub/shower combo)
• Guest bedroom with queen bed
• Guest bedroom with twin bed and trundle
• Full guest bathroom with tub/shower combo

Total Sleeping Arrangements
• 2 King beds
• 1 Queen bed
• 2 Twin beds

Outdoor Living

• Three parking spaces
• Private dock for fishing and relaxing
• Partially covered back porch with grill, table, and chairs
• Large backyard ideal for outdoor games and gatherings

Free Fun Package

Through our partnership with Xplorie, your stay includes one free pass per activity, per day:

November–February
• Urban Air Adventure Park
• Adventure Zone at Baytowne Wharf
• One round of golf at select courses

March–October
• Urban Air Adventure Park
• Adventure Zone at Baytowne Wharf
• Sea Blaster Dolphin Cruise
• The Gulfarium
• Golf at Regatta Bay, Emerald Bay, Windswept Dunes, Bluewater Bay, or Golf Garden

Pet Policy

• One dog allowed (maximum 40 lbs)
• $200 non-refundable pet fee
• Housebroken dogs only
• Puppies must be crated unless outside
• $350 additional cleaning fee if excessive shedding or accidents are not addressed
• Dogs are not allowed on furniture, bedding, or Okaloosa County beaches
• Guests are responsible for all pet-related damages

Starter Amenities

A starter kit is provided for your arrival and includes:

• Trash can liners
• Dishwashing soap and dishwasher detergent
• Hand soaps, shampoo
• Two rolls of toilet paper per bathroom
• One roll of paper towels

Security

For guest safety, a Ring camera is located at the front door and an additional security camera is positioned at the rear of the property.

Policies

• No smoking inside the home
• Please remove evidence of smoking outside
• Primary renter must be 25 or older
• No events or parties without prior approval

Check-In / Check-Out

Check-in: 4:00 PM CST
Check-out: 10:00 AM CST

Bailey’s Bayside offers the rare combination of quiet waterfront living, boating access, pet-friendly flexibility, and proximity to the very best of Destin and 30A. It is the perfect retreat for those who want both relaxation and adventure on the Emerald Coast.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly
  • BEACH

    Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 1692 Sq Ft (157 Sq M)
  • KITCHEN

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

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi, With Speed Of 50+ Mbps
  • OUTDOORS

    Barbecue Grill Garden Patio
  • BATHROOMS

    2.5 Bathrooms Bathtub Or Shower Hair Dryer Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Birdwatching Nearby Fishing Nearby Golf Nearby Jet Skiing Nearby Kayak On Site Marina Nearby Sailing Nearby Snorkeling Nearby Water Park Water Tubing Nearby Windsurfing Nearby
  • ENTERTAINMENT

    Books Games Smart TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    Near A Hospital Near Outlet Shopping Near The Bay Near The Sea On The Waterfront
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 8

Map Map

School District Rates & Availability

Review Review

  • George P.

    Submitted Jul 21, 2025

    Stayed Jul 3, 2025

    Great Stay!

  • KARLY V.

    Submitted Jun 24, 2025

    Stayed Jun 19, 2025

    We loved the house. Location was great close to everything. Very clean right on the water easy access to us to park our personal boat to use while we were there. Would recommend to anyone

  • Cindy B.

    Submitted May 12, 2025

    Stayed May 8, 2025

    We were in town for a wedding. Our host was so quick at responding to my questions. The property was just as described. It rained most of the weekend but even that was relaxing! We enjoyed the view, sitting on the back porch drinking coffee! Cornhole came in handy and we had one venture out a couple of times in the Kayaks. Plenty of sleeping and beds were very comfortable!

  • William B.

    Submitted Mar 11, 2025

    Stayed Mar 1, 2025

    We had a great time at Baileys. It was perfect for our needs. Plenty of room for us. Pet friendly. It’s on a nice quiet bayou. We wanted a place that we could leave our boat in the water behind the house. Even though it’s very shallow we were able to get in and out with our bay boat. If I had to come up with a negative it was the amount of traffic in front of the home. Renda was great to work with. Would book again.

  • Jennifer H.

    Submitted Aug 9, 2024

    Stayed Jul 12, 2024

    Spent a week at this location in July 2024. The backyard and waterfront view was great! We brought our boat and boated as often as we could. The house is located on a busier street. Property manager was very responsive, we had no problems the week we rented.

  • JEFF C.

    Submitted Apr 30, 2024

    Stayed Apr 1, 2024

    What an enjoyable time at this property! Dock was perfect for our 18 foot center console. Neighbors were friendly and property was perfectly functional for our and our family needs. Great location close and convenient to required shopping and great restaurants. Our host was magnificent. She was incredibly responsive and ensured that our stay was pleasant.

  • Tim J.

    Submitted Mar 12, 2024

    Stayed Feb 18, 2024

    This home was very clean no bugs and had 3 large bedrooms and a smaller bedroom. I liked the back porch and deck plus the view of bayou. I disliked the busy street in front of the house, no voice activated control on the main room tv and could open only the kitchen window to get fresh air and it had no screen. Tried to open doors but attracted bugs. Overall rating 4 out of 5.

  • Julie R.

    Submitted Nov 4, 2023

    Stayed Dec 31, 1969

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The vacation rental was perfect for our family which consisted of grandmother, grandfather, mom, dad and 2 year old son/grandson. Bailey's Bayside provided everything we needed to enjoy our vacation.The layout of the house provided enough space for all of us. The back yard and back deck was very enjoyable. The area was peaceful,quite, and safe. I would certainly recommend this rental. Our hostess was fantastic and extremely kind. We enjoyed our stay!

  • Katie M.

    Submitted Jul 25, 2023

    Stayed Dec 31, 1969

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Had a great time and we will be back

  • Kellie G.

    Submitted Jul 20, 2023

    Stayed Dec 31, 1969

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Very spacesious and homey, beautiful bay view also easily accessible to other locations including multiple beach public beaches

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Total

Includes taxes and fees
$458+
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