Steps to Seaside Avenue, Pools, Park & Beach in Seaside + 2 Adult Bikes!

Santa Rosa Beach, Florida
$1069 avg/night Minimum Stay 1 Nights
Bed 4

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 8

Max Sleeps

Night 1 nights

Min Stay

*Please be advised that neighboring properties may currently be undergoing construction or renovation during your stay. As a result, intermittent noise or construction-related activity may occur at certain times throughout the day. This work is managed by third parties outside of our control, and we appreciate your understanding while enjoying the property. For additional questions or concerns regarding nearby construction activity, please contact Homeowner’s Collection at

*Construction Notice - Third-party construction is occurring on an adjacent lot across from this residence and may be visible or audible during permitted hours. In Seaside, Florida, construction hours are Monday–Saturday, 8 AM–6 PM. Please contact the Homeowner’s Collection team atto inquire on construction details.

Welcome to Bobby D's- a four-bedroom, 2-story retreat, nestled in the heart of all things Seaside, FL. This home has a prime location only a 5-minute walk to the beach, steps to Seaside Ave., the family pool, and the park. Walk to over 35 shops and restaurants just steps from your front door and only a 4-minute walk to the Seaside Amphitheater. At Bobby D’s, you’ll relax with family and friends at mealtime in the gourmet kitchen and on the open-air front porch overlooking the lighted side yard and seating area.

The eat-in kitchen offers granite countertops, a Viking gas range, and stainless appliances throughout. The thoughtful layout allows for 3 bar stools and a small flat-screen TV so that no one misses their favorite shows. The dining area offers seating for 6 in a designated dining area enhanced by a gas fireplace and original artwork. A half-bathroom is conveniently situated just off the kitchen. The living room is the perfect place for everyone to gather, with the vast sectional sofa before a 40-inch flat-screen TV and DVD player. Gorgeous hardwood floors run throughout. The primary king suite is located downstairs and has its own ensuite bathroom. This king has its own mounted flat-screen TV, a chase lounge, and a large private ensuite bathroom with dual vanities, a soaker tub, and a glass-enclosed walk-in shower.

As you head up the stairs to the second floor, you’ll see that the owner of Bobby D’s is the renowned songwriter, Bobby D, who wrote the #1 Montgomery Gentry song, Gone, with Jeff Steele on the top balcony! Bobby has also worked with the likes of Vince Gill, Tim McGraw, and Faith Hill, and his gift for making music is matched only by his taste in décor.

Upstairs, you’ll find three more bedrooms. The second bedroom is a secondary king primary bedroom with its own ensuite bath. This generous king bedroom has a dresser, a mounted flat-screen TV, and closets. The private bathroom has granite dual vanities and a glass-enclosed shower. The third bedroom up features a queen bed with a flat-screen TV and windows with plenty of natural light and a full shared bathroom just outside. This shared full bathroom features a single vanity with a tub/shower combination that is shared with the adjacent fourth bedroom. The fourth bedroom opens with French doors, revealing two twin beds, a TV, and a DVD player, making it perfect for kids and adults alike. A beautifully situated balcony is just across the hall. Here you can share a cocktail with family and friends as you overlook the rooftops of Seaside and take in the serenity.

After a day at the beach, rinse off in the outdoor shower and barbecue on a charcoal grill located off the side porch. The shaded walking trails running throughout Seaside can be accessed through the picket fence to the north. The famed shops and boutiques are within easy walking distance.

* 5 nt. min. Spring, Spring Break & Summer; 3 nt. min. Fall; 2 nt. min. Winter. Must be 25 years of age to rent & sign registration.

Features:
* 2,311 square feet
* Private Seaside Residential Beach at East Ruskin Pavilion, the largest private beach on 30A
* 5-minute walk, 352 yards to the beach
* Lighted outdoor sitting area
* Enclosed outdoor shower
* Washer & Dryer
* Peacock Alley Linens - Fresh and luxurious Peacock Alley towels and sheets throughout the home
* Access to 3 swimming pools, 5 Clay & 3 Pickleball courts (court fees apply), and a fitness center
* Welcome tote with 2 beach towels, a complimentary bottle of wine, and 2 complimentary rental bikes for pickup at Seaside Transit
* Personalized service throughout your stay & starter amenities provided
* 2 parking passes. A golf cart is considered a car. Special circumstances and medical needs requests require a golf cart permit
* No pets allowed

STR23-002237

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

Feature Features

  • PETS

    No Pets Allowed
  • 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) Deadbolt Lock 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: 2311 Sq Ft (215 Sq M)
  • KITCHEN

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

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi, With Speed Of 100+ Mbps (good For 1–2 People Or Up To 6 Devices)
  • OUTDOORS

    Balcony Charcoal Grill
  • POOL/SPA

    Heated Pool Massages Shared/communal Pool
  • BATHROOMS

    3.5 Bathrooms Bathtub Or Shower Hair Dryer Jetted Bathtub Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Basketball Nearby Cycling Nearby Ecotours Nearby Fishing Nearby Fitness Center Fitness Facilities Nearby Golf Nearby Snorkeling Nearby Surfing/body Boarding Nearby Swimming Nearby
  • ENTERTAINMENT

    DVD Player Smart TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    Near A Hospital Near The Sea
  • SERVICES AND CONVENIENCES

    Concierge Services Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Cobblestone Flooring In Public Areas Hardwood Flooring In Public Areas If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. 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

  • Kevin M.

    Submitted Jul 19, 2025

    Stayed Jul 11, 2025

    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: Homeowners Collection made booking through departure a breeze. We will be back!

  • Kimberly K.

    Submitted Jun 12, 2025

    Stayed Jun 7, 2025

    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: We had a wonderful time at Bobby D's. House was perfect for our needs. Very comfortable, clean, and conveniently located. Seaside is family favorite for us.

  • Jennifer F.

    Submitted Jan 6, 2025

    Stayed Dec 29, 2024

    We booked a last minute stay over new years and were delighted with our decision. Adorable area. We were walking distance from everything. Cottage came with 2 rental bikes, which were fun to use. Loved the whole city. Cottage was equipped with everything we needed. Text communication with property manager was easy and helpful.

  • Lee M.

    Submitted Jul 31, 2024

    Stayed Dec 31, 1969

    Rating Details: The property manager was more than helpful. The vacation rental was very clean. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Bobby D’s was a great experience for our family. The location was convenient to the beach, pool, gym and retail. Seaside was a nice place to relax and enjoy family time!

  • Ken H.

    Submitted Nov 27, 2023

    Stayed Nov 22, 2023

    It’s difficult to use enough superlatives, but this was incredible. The house is huge, has a gourmet kitchen that worked perfectly for our Thanksgiving dinner, and is in the perfect location. And being a big fan of Bob DiPiero for many years, being in his place with his gold records was a wonderful bonus. Lastly, I have stayed in numerous VRBO properties, but the property manager, Homeowners Collection, was perhaps the best I’ve encountered. They were highly communicative, and I couldn’t believe how quickly they responded to each text. We will be back!

  • Wendy M.

    Submitted Jul 24, 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: Our family of 4 plus friends really enjoyed Bobby D's! Plenty of room, comfortable and fun, had just about everything we needed for an amazing vacation! Loved the location in Seaside! Would love to stay here again!Our only issues were a smoke alarm that went off EVERY time we opened the oven door, and r had to keep resetting the wifi router for internet access. The management company was very responsive. Comfortable beds, plenty of towels and toiletries!

  • Jean D.

    Submitted Jul 14, 2023

    Stayed Jul 6, 2023

    Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Other than having sporadic internet service, the house was as described. The modem was replaced on our final day, so maybe that problem is resolved Basic condiments/ spices are not provided, so plan to bring your own.

  • Julie T.

    Submitted Mar 19, 2023

    Stayed Mar 12, 2023

    One of THE best places Ive stayed at in Seaside. The kids has a blast and I enjoyed the easy location.

  • Hollan F.

    Submitted Jul 4, 2022

    Stayed Jun 12, 2022

    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 house was in a great location very clean and comfortable

  • A guest from Kat....

    Submitted Jun 7, 2022

    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: Everything was absolutely perfect! Checking in was a breeze, the home was in immaculate shape, and had ALL of the amenities you would have in your own home. The customer service from Homeowner's Collection was stellar. We received a nice welcome package and continuously received text messages giving us valuable information during our stay. Bobby D's cottage is in a very convenient location and we would definitely recommend it! The food trucks, restaurants, shopping, and the beach was all in walking distance. It all made for a wonderful family vacation!

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Total

Includes taxes and fees
$1,069+
View details