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4 BR
3.5 BA
8 Guests

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WELCOME TO BOBBY D'S IN THE HEART OF SEASIDE, FLFRONT PORCH W/ROCKERS PERFECT FOR MORNING COFFEEOPEN AIR PORCH OFF BEDROOMS ON SECOND FLOORADJACENT KITCHEN W/BAR SEATING FOR THREESECOND KING BEDROOM ON SECOND FLOORPRIVATE DRIVEWAY FOR 2, WALK TO POOL AND AMENITIESFOREST STREE W/OFF STREET PARKING BY HOMEPRIVATE YARD AND PORCHES, AMAZING LOCATION, WALK TO BEACHGRAND KITCHEN AND OPEN FLOOR PLAN ON FIRST LEVELEXPANSIVE LIVING, FOUR BEDROOM COTTAGE, SLEEPS 8PRIVATE SIDE YARD W/LIGHTED SEATING AREA & FOUNTAINLARGE SECTIONAL AND FLAT SCREEN TVLIVING AREA ALTERNATE VIEW TO ENTRANCEKITCHEN WITH ALL STAINLESS APPLIANCESCOMPLETE W/ICE MAKER AND A WINE & BEVERAGE DRAWERSGOURMET DOUBLE OVEN W/SIX GAS BURNER & GRIDDLE!LARGE DOUBLE DOOR SUB ZERO FRIDGEKITCHEN AND DINING AREA ALTERNATE VIEWADJACENT DINING AREA FOR SIXVIEW OF KITCHEN FROM DINING AREASITTING AREA WITH PORCH ACCESS AND FIREPLACESECOND SIDE PORCH WITH COMFORTABLE SEATINGSECOND SIDE PORCH W/ACCESS TO OUTDOOR LIGHTED SIDE YARDPRIVATE SIDE YARD WITH BUILT IN CHARCOAL GRILLFIRST FLOOR HALF BATHROOM OFF OF LIVING AREASFIRST BEDROOM, KING PRIMARY DOWNKING MASTER W/FLAT SCREEN & SEATING AREAKING MASTER WITH OUTDOOR ACCESSKING MASTER ALTERNATE VIEW TO MOUNTED FLAT SCREENMASTER PRIVATE BATH, DUAL VANITIES W/SOAKER TUBCOMPLETE W/SOAKER TUB & WALK IN SHOWERSTAIRCASE TO SECOND FLOOR & 3 OTHER BEDROOMSSECOND KING PRIMARY W/FLAT SCREEN & ENSUITE BATHKING BEDROOM SECOND FLOOR ALTERNATE VIEWPRIVATE BATH W/DUAL VANITIES & GLASS ENCLOSED SHOWERTHIRD BEDROOM, QUEEN ON 2ND FLOORQUEEN W/PRIVATE TVQUEEN ALTERNATE VIEWSHARED HALL FULL BATH, SINGLE VANITY & TUB/SHOWER COMBOFOURTH BEDROOM, 2ND FLOOR, TWO TWINSTWO TWINS ADJACENT TO UPSTAIRS BALCONYUPPER HALLWAY WITH ACCESS TO BALCONYLARGE SECOND FLOOR LAUNDRY ROOMBACKYARD WITH WOODEN PATHWAY & OUTDOOR SHOWERENCLOSED OUTDOOR SHOWERGUEST WELCOME COOLER SET UP UPON ARRIVALPRIVATE SEASIDE RESIDENTIAL BEACH ACCESS AT EAST RUSKIN PAVILIONLARGEST STRETCH OR PRIVATE RESIDENTIAL BEACHES ON 30ALOCATED JUST 5 MINUTE WALK TO PRIVATE SEASIDE BEACHESCATCH A BEACH SUNSETSTEPS FROM AMENITIES CENTERTHE FAMOUS BUD & ALLEY'S RESTAURANTBLACKBEAR BREAD CO.SEASIDE CENTRAL SQUARE SHOPS AND CONDOMINIUMSSEASIDE WEST SIDE POOL AND GRILLSEASIDE'S ICONIC POST OFFICEPICKLE'S RESTAURANTSEASIDE ADULT POOLSEASIDE KRIER PLAZA SHOPS AND RESTAURANTSSANDBAR - BEACHSIDE DRINKS
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Description

506 FOREST STREET

2 KINGS, 1 QUEEN, 2 TWINS

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

Amenities

Activities

  • Church
  • playground
  • restaurants
  • fitness center
  • Bicycles
  • Communal Pool
  • Heated Pool
  • basketball court
  • cycling
  • fishing
  • golf
  • swimming
  • tennis
  • Massage
  • Paddle Boarding
  • Shuffleboard
  • Shopping

General

  • Satellite / Cable
  • Internet
  • Staff

Comforts of Home

  • DVD Player
  • Fireplace
  • Iron & Board
  • Linens Provided
  • Media Every Room

Outdoor

  • outdoor shower
  • Parking
  • Balcony
  • Deck / Patio
  • Outdoor Grill
  • Porch

Beds and Baths

  • combination tub/shower
  • king bed
  • tub

Geographic

  • East Side
  • Town View

Availability

Key
#Night Available#Night Unavailable#Arrive Only#Depart Only
January 2026
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Location

Get Directions

Reviews

Seaside for a week at Bobby D’s

Reviewed on2025-07-19 by from Louisville, KY United States
Updated on 2025-07-19
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Homeowners Collection made booking through departure a breeze. We will be back!
Hello Charles, We so appreciate your time to share a positive review of Bobby D's Cottage and Homeowners Collection team.
We are delighted you enjoyed Seaside and would love to come back. We will welcome you with open arms. Take care.

Great time at Bobby D's

Reviewed on2025-06-12 by from Acworth, GA United States
Updated on 2025-06-12
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
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.
Hi Kimberly, We are delighted you found a favorite destination in Seaside. We hope to welcome you back again & again.
Thanks for taking the time to share a positive review of Bobby D's Cottage and Homeowners Collections.
Have a great rest of the summer!

Had a wonderful stay!

Reviewed on2023-07-23 by from Shelbyville, TN United States
Updated on 2023-07-23
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
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!
Thank you so much for taking the time to write this positive review of Bobby D's and the Homeowner’s Collection team. We always appreciate feedback and will absolutely pass yours on to our owners and operations team. We are so pleased you enjoyed your stay, and we hope to welcome you back on your next visit to Seaside!

Perfect family vacation

Reviewed on2022-07-03 by from Broussard, LA US
Updated on 2022-07-03
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
The house was in a great location very clean and comfortable
Thank you so much for taking the time to write this positive review of Bobby D's and the Homeowner's Collection team. We are so pleased you enjoyed your stay and we hope to welcome you back on your next visit to Seaside!

AirBnB Seaside, FL - Bobby D cottage

Reviewed on2022-06-06 by from Katy, TX United States
Updated on 2022-06-06
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
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!
Thank you so much for taking the time to write this positive review for Bobby D's and the Homeowner's Collection team. We are so pleased you enjoyed your stay and we hope to welcome you back on your next visit to Seaside!

May '22 stay

Reviewed on2022-05-23 by from Atlanta, GA United States
Updated on 2022-05-23
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4
Great family week in Seaside. HC was responsive when needed and not at all intrusive. House was great.
Thank you so much for taking the time to write this positive review of Bobby D's and the Homeowner's Collection team. We are so pleased you enjoyed your stay and we hope to welcome you back on your next visit to Seaside!

May '22 stay

Reviewed on2022-05-23 by from Atlanta, GA United States
Updated on 2022-05-23
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4
Great family week in Seaside. HC was responsive when needed and not at all intrusive. House was great.
Thank you so much for taking the time to write this positive review of Bobby D's and the Homeowner's Collection team. We are so pleased you enjoyed your stay and we hope to welcome you back on your next visit to Seaside!

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