Bobby D's

506 FOREST STREET

Please be advised that there is construction located south of this home between Seaside and Watercolor for Seaside improvements, we apologize for this inconvenience. Construction completion date is Jan. 2026. 

Bobby D’s | A Luxury Seaside Cottage Surrounded by Nature

Tucked among lush greenery and mature trees, Bobby D’s offers a rare blend of coastal elegance and peaceful privacy in the heart of Seaside, Florida. This beautifully appointed two-story, four-bedroom retreat is just steps from the family pool, neighborhood parks, and Seaside Avenue, with East Ruskin Pavilion beach access only a five-minute walk away. While the setting feels serene and tucked away, you’re moments from everything that makes Seaside iconic.

Outdoor Living & Arrival Experience

Guests arrive to designated off-street parking directly in front of the home and are welcomed by a charming open-air front porch with two rocking chairs—an ideal spot for morning coffee or evening conversations. The porch overlooks a private, landscaped yard featuring a softly lit seating area and a tranquil fountain, creating a calming soundtrack to your stay.

Open Living Spaces for Gathering & Relaxation

Inside, Bobby D’s opens to a spacious living room designed for connection and comfort. A large wraparound sectional and mounted flat-screen TV make it perfect for movie nights after long beach days. Natural light and thoughtful design create an inviting atmosphere that encourages guests to unwind together.

Gourmet Kitchen & Dining

The renovated gourmet kitchen is a true standout, fully equipped for both everyday meals and special occasions. Features include upscale Viking appliances, a gas range with griddle, double ovens, icemaker, and beverage drawers. A high-top kitchen bar with additional seating and its own flat-screen TV keeps the entire group connected, while the adjacent dining area offers ample space for shared meals. A convenient half bath is located just off the kitchen on the main level.

Main-Level Primary Suite

The first-floor king primary suite provides a private retreat within the home. Thoughtfully designed with a chaise lounge seating area, large flat-screen TV, and custom built-in storage, the space is ideal for longer stays. The ensuite bathroom features dual vanities, a whirlpool soaking tub, and a glass-enclosed walk-in shower for spa-like relaxation.

Upstairs Bedrooms & Musical Legacy

Ascending the staircase, guests discover the inspiration behind the home’s name. Bobby D’s is owned by legendary songwriter Bobby DiPiero, and the second floor celebrates his musical legacy with records and plaques throughout—some of his iconic songs were written right here.

Upstairs includes three generously sized bedrooms:

• A secondary king primary suite with dual walk-in closets, flat-screen TV, and a private ensuite bath featuring dual vanities and a glass-enclosed walk-in shower
• A queen guest bedroom with ample storage and flat-screen TV
• A twin bedroom with two beds, private TV, and DVD player—perfect for younger guests

The queen and twin rooms share a well-appointed hall bath with a tub/shower combination.

Elevated Outdoor Spaces

Just off the upstairs hallway, a furnished balcony overlooks Seaside’s treetops, offering a quiet perch for reading, afternoon cocktails, or unwinding under the stars. It’s the perfect complement to the home’s indoor living spaces.

Your Seaside Sanctuary

Whether you’re drawn to the beach, the peaceful natural surroundings, or the rich character woven into every detail, Bobby D’s delivers a refined Seaside experience rooted in luxury, comfort, and tranquility. From its prime location to its thoughtful design, this home invites you to relax deeply and return year after year.

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

FEATURES

• 2,311 square feet of spacious, thoughtfully designed living space
• Private Seaside residential beach access at East Ruskin Pavilion
• Seaside features the largest private residential beach on Scenic 30A
• 352 yards (4-minute walk) to beach access
• Outdoor charcoal grill for casual cookouts
• Conveniently located near the family pool and playground
• Televisions in every bedroom
• Deep soaking tub for relaxation after beach days
• Enclosed outdoor shower
• Gourmet, fully renovated kitchen featuring an icemaker and double ovens
• Washer and dryer
• Peacock Alley linens throughout the home, offering fresh, luxurious sheets and towels
• Access to 3 swimming pools, 5 clay tennis courts, 3 pickleball courts (court fees apply), and a fitness center
• Welcome tote with 2 beach towels, a complimentary bottle of wine, and 2 rental bikes for pickup at Seaside Transit Authority
• Personalized guest services throughout your stay with starter amenities provided
• Parking passes: 2 passes issued for two-bedroom and larger homes. Golf carts are considered vehicles. Golf carts are prohibited for non-homeowners visiting Seaside. Special circumstances and medical needs require an approved golf cart permit
• No pets allowed

STR23-002237