Bailey's Bayside, nestled in a quiet residential area of Santa Rosa Beach, offers the perfect retreat for relaxation and nature. With 85' of private waterfront on Buck Bayou and kayak access to explore the surrounding waters or fish from the dock. Take advantage of free daily activities like dolphin cruises or visit Gulfarium Marine Adventure Park.
Reviews
9.89.8 out of 10
Exceptional
Entire home
4 bedrooms3 bathroomsSleeps 81692 sq ft
Popular amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Free Wi-Fi
Air-conditioning
Add dates for prices
About this property
Waterfront~Sleeps 12~4BD 2.5BA~Pet Friendly~Kayaks~Boats Welcome~On the Bay
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.
Property amenities
Beach
Beach nearby
Internet
Available in the house: Free WiFi
Parking and transport
Parking on site
Kitchen
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Hob
Microwave
Oven
Refrigerator
Spices
Toaster
Dining
Dining table
Bedrooms
4 bedrooms
Bedsheets provided
Bathroom
2.5 bathrooms
Bathtub or shower
Hair dryer
Towels provided
Living spaces
Dining table
Living room
Entertainment
Books
Games
Smart TV with cable/satellite channels
Outdoor areas
Barbecue grill
Garden
Patio
Laundry
Laundry facilities
Washing machine
Comfort
Air conditioning
Heating
Pets
Pet friendly
Suitability/Accessibility
Smoke-free property
Services and conveniences
Iron/ironing board
Location highlights
Near a hospital
Near an outlet shopping centre
Near the bay
Near the marina
Near the sea
On the waterfront
Things to do
Kayak
Water park
Birdwatching nearby
Fishing nearby
Golfing nearby
Jet skiing nearby
Sailing nearby
Scuba diving nearby
Snorkelling nearby
Surfing/bodyboarding nearby
Swimming nearby
Water skiing nearby
Water tubing nearby
Windsurfing nearby
Safety features
Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
Smoke detector (host has indicated there is a smoke detector on the property)
Fire extinguisher
General
Garden
Unit size: 1,692 square feet
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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
Pets
Pets are allowed
Service animals are welcome, and 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
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
About the area
Located in Santa Rosa Beach, this holiday home is on the waterfront. Grand Boulevard at Sandestin and Baytowne Wharf are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Miramar Beach and Destin Beaches. Big Kahuna's Water and Adventure Park and Blast Arcade and Laser Maze are also worth visiting. Looking to get your feet wet? Jet skiing, scuba diving and snorkelling adventures can be found near the property. Visit our Santa Rosa Beach travel guide
Sandestin Golf Resort - Raven, Burnt Pine, Baytowne, The Links
8 min drive - 5.4 miles
Blue Mountain Beach
18 min drive - 14.7 miles
Seaside Beach
24 min drive - 20.0 miles
Burnt Pine Golf Club
17 min walk - 1.0 mile
Getting around
Fort Walton Beach, FL (VPS-Northwest Florida Regional)
43 min drive
Restaurants
Starbucks
7 min drive
Grimaldi's Pizzeria
6 min drive
Kilwin's In Grand Boulevard
6 min drive
Cantina Laredo
7 min drive
Craft Bar Grande Blvd
6 min drive
Frequently asked questions
Is Waterfront~Sleeps 12~4BD 2.5BA~Pet Friendly~Kayaks~Boats Welcome~On the Bay pet-friendly?
Yes, pets are allowed at this property.
How much is parking at Waterfront~Sleeps 12~4BD 2.5BA~Pet Friendly~Kayaks~Boats Welcome~On the Bay?
On-site parking is available at the property.
What time is check-in at Waterfront~Sleeps 12~4BD 2.5BA~Pet Friendly~Kayaks~Boats Welcome~On the Bay?
Check-in begins at 4:00 PM.
What time is check-out at Waterfront~Sleeps 12~4BD 2.5BA~Pet Friendly~Kayaks~Boats Welcome~On the Bay?
Checkout is at 10:00 AM.
Where is Waterfront~Sleeps 12~4BD 2.5BA~Pet Friendly~Kayaks~Boats Welcome~On the Bay located?
Situated on the waterfront, this holiday home is steps from Choctawhatchee Bay and within 3 mi (5 km) of Ascension Sacred Heart Hospital Emerald Coast and Ascension Sacred Heart Emerald Coast. Grand Boulevard at Sandestin and Grand Boulevard Farmers' Market are also within 3 miles (5 km).
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Waterfront~Sleeps 12~4BD 2.5BA~Pet Friendly~Kayaks~Boats Welcome~On the Bay Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers 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.
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.
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.
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!
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.
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.
Tim J.
Stayed 19 nights in Feb 2024
From a partner site
10/10 Excellent
Julie R.
4 Nov 2023
Florida family fun
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!
House is located at great convenient location - close distance from beach, retails, grocery and state parks. We have enjoyed our stay and the house is very clean.
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
Quiet area and peaceful back yard with beautiful view! Our family enjoyed hanging at the house and the location was great for visiting both Destin and Panama City Beach. The manager was very responsive and helpful with any questions we had!
Renda was one of the best hosts we have ever encountered. She was easy to communicate with and very accommodating. We loved the house and the location.
Summer W.
Stayed 2 nights in Feb 2023
From a partner site
10/10 Excellent
Katie M.
25 Jul 2023
4th of July Vacation
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
Great location and great if you have your own boat.
House was clean and neighbors were friendly. Was able to keep our boat houses dock all week. Short drive to Destin and plenty of stores. Would stay again with family or guy's fishing trip. Property manager always picked up and was very helpful.
Justin P.
Stayed 7 nights in Apr 2023
From a partner site
10/10 Excellent
James C.
17 Apr 2023
Home away from home
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:
Beautiful house, 2 kings size beds up stairs! Very clean! Close by to everything but far enough away that the nights are quiet. Renda is awesome and was there for anything we needed! Owners are very accommodating! Was hoping for a little more water depth at the dock but we knew the water was going to be low. Definitely going back!
James C.
Stayed 5 nights in Apr 2023
From a partner site
10/10 Excellent
Kellie G.
20 Jul 2023
Cozy get away
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
Kellie G.
From a partner site
10/10 Excellent
michelle e.
27 Jun 2023
Great Bay Getaway
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:
What a sweet and peaceful house - perfect for our family of 6. Very clean and well stocked. Bring your boat and enjoy easy access to the bay. Management team is amazing! Look forward to going back next year!! 🏅
michelle e.
From a partner site
10/10 Excellent
A guest from ,
22 Jun 2023
Awesome
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:
Was very pretty inside and out. Plenty of room and a great location.