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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 SHOWERPRIVATE 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 OFFICEAMENITIES INCLUDED IN YOUR STAYPICKLE'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. 

If you are looking for a place to enjoy the beach, nature, or beautiful views, Bobby D’s is just the place for you. This  Seaside cottage is surrounded by lush trees and shrubs that you may not expect in a palm tree-laden climate. However, the inside of this 2-story, four-bedroom retreat is exactly what you’d expect in the most luxurious vacation cottage imaginable. Bobby D's has a prime Seaside, location just steps from the family pool, parks, and Seaside Avenue just around the corner. As well as an easy walk or bike ride to the beach at East Ruskin Pavilion just a 5-minute walk away from your front door. Upon arrival, you have designated off-street parking for one in front of the home. Step inside and you are greeted by an open-air front porch with two rockers, the perfect morning coffee location. This porch overlooks a private yard with a lighted seating area for four more with the soothing sounds of the majestic fountain in the background.

As soon as you walk in the door, you’ll find a spacious, open living room with a large wrap-around sectional and a large flat-screen TV in a very open and generously sized living room perfect for movie nights after long sun-filled beach days.  Make your way into the kitchen and dining area, and you’ll find a renovated gourmet kitchen complete with an icemaker, extra beverage drawers, a gas range with griddle, double ovens, and upscale Viking appliances.  There’s also a high-top kitchen bar with flat-screen TV and additional seating for three more to keep the family connected.  A half bathroom is conveniently located on the first floor just off the kitchen for the common living areas. 

The primary king suite is located on the first floor with an ensuite private bathroom. This generous primary suite features a chaise lounge seating area, a large mounted flat-screen TV, and ample custom built-in storage for any length of stay. The private bathroom has dual vanities, a whirlpool bathtub, and a glass-enclosed walk-in shower.   As you walk up to the second floor, you’ll find out why this home is named Bobby D’s. An array of music records and plaques tell you that Bobby D is the famous songwriter Bobby DiPiero. Did you know that some of his songs were actually written in this very house?  At the top of this staircase, you will find all three oversized bedrooms.  The second bedroom is the secondary primary king suite with large dual walk-in closets, a great ensuite double vanity bathroom, and private flat-screen TV. The ensuite primary bathroom has dual vanities, a large mirror, and a glass-enclosed walk-in shower.  The primary bedroom's stunning white walls and large, white bedspread are so fresh and clean that you’ll awake refreshed every morning!

The third bedroom, a queen, is located down the hall and has ample storage, its own flat-screen TV, and shares an adjacent hall bath with the twin bedroom.  Just outside the queen bedroom, you will find the shared bathroom with a combination tub/shower and single vanity.  The fourth bedroom has two twin beds (perfect for the kids) and has a private TV, DVD player and opens with French doors into a generous sized twin bedroom with 2 twin beds and its own private large flat-screen TV.  Just a few steps away, you’ll find the upstairs furnished outdoor balcony overlooking the treetops of Seaside perfect for an afternoon book or cocktails with friends. Wherever your vacation takes you, Bobby D’s will relax and lull you to sleep every night. It’s the perfect vacation destination for anyone seeking luxury and peace. 

* 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

  • Features 2,311 square feet
  • Seaside Private Residential Beach at East Ruskin Pavilion
  • Seaside is the largest residential private beach on 30A
  • 352 yards or 4-minute walk to beach access
  • Outdoor charcoal grill
  • Close to the family pool and playground
  • TVs in every bedroom
  • Deep soak tub
  • Enclosed Outdoor shower
  • Gourmet renovated kitchen with icemaker and double oven
  • Washer and dryer 
  • Peacock Alley Linens - Fresh and luxurious Peacock Alley towels and sheets throughout the home
  • 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, complimentary bottle of wine, and 2 rental bikes with stay for pickup at Seaside Transit Authority
  • Personalized service throughout your stay and starter amenities provided
  • 2 parking passes for two-bedroom and larger homes are issued. A golf cart is considered a car.  Golf carts for non-homeowners visiting Seaside are prohibited. Special circumstances and medical needs requests require a golf cart permit.   
  • No pets

STR23-002237

Amenities

Activities

  • Church
  • live theater
  • 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
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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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