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

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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

9.8 out of 10
Exceptional

Entire home

4 bedrooms3 bathroomsSleeps 81692 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi
  • Air conditioning

Add dates for prices

About this property

Entire place

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

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 transportation

  • Parking on site

Kitchen

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

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near a hospital
  • Near an outlet shopping mall
  • Near the bay
  • Near the marina
  • Near the sea
  • On the waterfront

Things to do

  • Golf
  • Kayak
  • Tennis
  • Water park
  • Birdwatching nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling 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

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 10:00 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

Pets

Pets 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

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
Onsite 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 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

Property is also known as

2960-244099

About the area

Located in Santa Rosa Beach, this vacation 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 snorkeling adventures can be found near the property. Visit our Santa Rosa Beach travel guide
View more Vacation homes in Santa Rosa Beach
Map
Santa Rosa Beach, FL

What's nearby

  • A picture of Baytowne Wharf at Destin Florida
    Baytowne Wharf
    4 min drive - 2.5 km
  • Destin_SandestinGolfResortRavenBurntPineBaytowneTheLinks_553248621532653504_02
    Sandestin Golf Resort - Raven, Burnt Pine, Baytowne, The Links
    7 min drive - 4.9 km
  • Pathway and sea oats on beach at Santa Rosa Island near Pensacola, Florida; Shutterstock ID 104491910; purchase_order: SP-1269 HA 2018 Batch 1; Order: ; client: ; other:
    Blue Mountain Beach
    17 min drive - 19.2 km
  • Dramatic pastel light sunset with sun rays in Santa Rosa Beach, Florida with Pensacola coastline coast cityscape skyline in panhandle and ocean
    Seaside Beach
    24 min drive - 29.5 km
  • Burnt Pine Golf Club
    14 min walk - 1.2 km

Getting around

  • Northwest Florida Regional Airport (VPS)
    43 min drive

Restaurants

  • Starbucks
    7 min drive
  • Kilwin's In Grand Boulevard
    6 min drive
  • Grimaldi's Pizzeria
    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?

Onsite 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?

Check-out 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 vacation 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 mi (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.
More informationOpens in a new window
Rating 10 - Excellent. 16 out of 18 reviews
Rating 8 - Good. 2 out of 18 reviews
Rating 6 - Okay. 0 out of 18 reviews
Rating 4 - Poor. 0 out of 18 reviews
Rating 2 - Terrible. 0 out of 18 reviews

10

Cleanliness

9.4

Location

Reviews

Verified

10/10 Excellent

JEFF C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Boating Paradise

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.
Stayed 25 nights in Apr 2024
Verified

8/10 Good

Jennifer H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Vacation

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.
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

Cindy B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very Relaxing Wedding Weekend

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!
Stayed 4 nights in May 2025
Verified

10/10 Excellent

William B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Baileys

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.
Stayed 7 nights in Mar 2025
Verified

8/10 Good

Tim J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice place to visit

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.
Stayed 19 nights in Feb 2024
From a partner site

10/10 Excellent

Julie R.

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!
Verified

10/10 Excellent

George P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Destin House

Great Stay!
Stayed 3 nights in Jul 2025
Verified

10/10 Excellent

KARLY V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Vann vacation

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
Stayed 3 nights in Jun 2025
Verified

10/10 Excellent

Bee T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location and a lot of rooms

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.
Stayed 4 nights in Dec 2022
Verified

10/10 Excellent

Brooke P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quiet and peaceful

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!
Stayed 5 nights in Mar 2023
Verified

10/10 Excellent

Summer W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Loved it!

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.
Stayed 2 nights in Feb 2023
From a partner site

10/10 Excellent

Katie M.

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
Verified

10/10 Excellent

Justin P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 7 nights in Apr 2023
From a partner site

10/10 Excellent

James C.

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!
Stayed 5 nights in Apr 2023
From a partner site

10/10 Excellent

Kellie G.

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
From a partner site

10/10 Excellent

michelle e.

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!! 🏅
From a partner site

10/10 Excellent

A guest from ,

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.
Verified

10/10 Excellent

Simmons Custom G.

Stayed 5 nights in May 2025