Entire home
Waterfront~Sleeps 12~4BD 2.5BA~Pet Friendly~Kayaks~Boats Welcome
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Reviews
9.8 out of 10
Exceptional
4 bedrooms2+ bathroomsSleeps 81692 sq ft
Popular amenities
Rooms & beds
4 bedrooms (sleeps 8)
Bedroom 1
1 King Bed
Bedroom 2
1 King Bed
Bedroom 3
1 Queen Bed
Bedroom 4
2 Single Beds
2 bathrooms, 1 half bathroom
Bathroom 1
Bathtub or shower · Toilet
Bathroom 2
Toilet
Bathroom 3
Bathtub or shower · Toilet
Spaces
Deck or patio
Porch or lanai
Kitchen
Garden
Dining area
About this property
Waterfront~Sleeps 12~4BD 2.5BA~Pet Friendly~Kayaks~Boats Welcome
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.
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.
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning
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10.0 out of 10, Exceptional, (32 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets 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 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
About the area
Santa Rosa Beach
Located in Santa Rosa Beach, this holiday home is on the waterfront. Big Kahuna's Water and Adventure Park is a popular attraction and the area's natural beauty can be seen at Miramar Beach and Destin Beaches. Blast Arcade and Laser Maze and Sirens at the Beach are also worth visiting. Looking to get your feet wet? Jet skiing, scuba diving and snorkelling adventures can be found near the property.

Santa Rosa Beach, FL
What's nearby
- Burnt Pine Golf Club - 14 min walk - 1.2 km
- Baytowne Wharf - 4 min drive - 2.5 km
- Sandestin Golf Resort - Raven, Burnt Pine, Baytowne, The Links - 7 min drive - 4.9 km
- Santa Rosa Beach - 12 min drive - 12.6 km
- Seaside Beach - 24 min drive - 29.5 km
Getting around
Restaurants
- Kilwin's In Grand Boulevard - 6 min drive
- Starbucks - 7 min drive
- Cantina Laredo - 7 min drive
- Grimaldi's Pizzeria - 6 min drive
- Craft Bar Grande Blvd - 6 min drive
Frequently asked questions
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
9.6/10
Location
10/10
Listing accuracy
Reviews
21 Jul, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Jul 2025
10/10 Excellent
KARLY V.
24 Jun, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Vann vacation
KARLY V.
Stayed 3 nights in Jun 2025
10/10 Excellent
Bee T.
31 Dec, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and a lot of rooms
Bee T.
Stayed 4 nights in Dec 2022
10/10 Excellent
Brooke P.
22 Mar, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Quiet and peaceful
Brooke P.
Stayed 5 nights in Mar 2023
10/10 Excellent
Summer W.
7 Mar, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved it!
Summer W.
Stayed 2 nights in Feb 2023
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Katie M.
25 Jul, 2023
4th of July Vacation
Katie M.
10/10 Excellent
Justin P.
9 Apr, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and great if you have your own boat.
Justin P.
Stayed 7 nights in Apr 2023
8/10 Good
Jennifer H.
9 Aug, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Vacation
Jennifer H.
Stayed 7 nights in Jul 2024
10/10 Excellent
JEFF C.
30 Apr, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Boating Paradise
JEFF C.
Stayed 25 nights in Apr 2024
10/10 Excellent
Cindy B.
12 May, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Very Relaxing Wedding Weekend
Cindy B.
Stayed 4 nights in May 2025
10/10 Excellent
William B.
11 Mar, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Baileys
William B.
Stayed 7 nights in Mar 2025
8/10 Good
Tim J.
12 Mar, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice place to visit
Tim J.
Stayed 19 nights in Feb 2024
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
James C.
17 Apr, 2023
Home away from home
James C.
Stayed 5 nights in Apr 2023
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Julie R.
4 Nov, 2023
Florida family fun
Julie R.
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Kellie G.
20 Jul, 2023
Cozy get away
Kellie G.
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
michelle e.
27 Jun, 2023
Great Bay Getaway
michelle e.
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
A guest from ,
22 Jun, 2023
Awesome
A guest from ,
10/10 Excellent
Simmons Custom G.
30 Jun, 2025
Simmons Custom G.
Stayed 5 nights in May 2025
About the host
Hosted by Renda Fisher
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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