Playing Hooky on 30a Santa Rosa Beach

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The ultimate in private, luxury homes!  Located on the south side of 30a, this house has plenty of room with 6 bedrooms, 4-1/2 baths and spaciously sleeps 21 people.  






Enjoy FREE Golf, FREE Bike Rentals, FREE Reef Beach Paddle Board, FREE Reef Beach Kayak and FREE Dave & Buster's Gift Card every day of your stay!
All activities are included for FREE with all new bookings!
*subject to seasonal availability
(one free admission per activity/per day)

Top Reasons to Book Playing Hooky on 30a - 

* Private beach access
* Gated community
* Fitness center on grounds
* Private balconies with views
* Large flat-screen televisions in each room
* Private pool
* Beach gear included
* Walk or bike to Gulf Place
* Minutes to Silver Sands Outlets, Baytowne Wharf, & Grand Boulevard
* Professionally Managed; 24/7 Service

Welcome to Playing Hooky on 30a, a luxury home nestled on the south side of 30a in South Walton perfect for large groups, small weddings, corporate retreats, and multiple families wanting to vacation together in paradise! This 3-story home sleeps 21 with plenty of room for everyone! With over 4200 sq. feet of a wonderfully laid out open floor plan, Playing Hooky on 30a offers large bedrooms, upscale furnishings, fully renovated and stocked kitchen, oversized laundry room with extra refrigerator, and three levels of wraparound porches and balconies to enjoy.  Located just 250 yards to the beach, Playing Hooky on 30a is located in a less crowded section of the South Walton beach, along the bike path, and only a few minutes’ walk to Gulf Place Town Center.  A large private pool is surrounded by nature with the pool deck offering plenty of chaise lounges and seating.

Upon entering the home, you’ll encounter a completely renovated coastal chic kitchen and living room with furniture, flooring, 65” Smart TV with DVD player, wine bar, fully equipped kitchen, with plenty of dining seating at a large table and the bar area. Also featured on this floor, an oversized laundry room with extra full refrigerator, and King bedroom with pull out Twin oversize chair and 55″ Smart TV.

The third story at Playing Hooky on 30a features a huge King Master Suite with a spacious sitting area with pull out Queen sleeper sofa and 55″ Smart TV.  The Master Suite also features an en suite bath with large double sinks, stand up tiled shower and Garden Tub, as well as views of the tranquil 30a scenery. Another King bedroom on the third floor adjoins a full bath.  A third bedroom on the third floor has a comfy Queen bed with a Queen pull out sleeper sofa.  All bedrooms have wall-mounted TVs.

The first floor offers access to the pool and pool deck as well as two additional bedrooms.  The Bunk Room features two bunk beds with Twins on top and Full-size beds on the bottom bunk – with easy access stairs for the top bunk!  The other bedroom on the first floor offers a King bed and a large flat-screen TV and DVD player.

San Remo condominium pool and workout facility access available to you for your stay!!  We have beach chairs, pool and beach toys, and a beach cart available at the house.

The pool can be heated from Oct-March for an additional $455+ tax/week
with a 48-hour notice.

No smoking, no parties and no pets, please

Under 25 must be accompanied by a parent or legal guardian on premises. Our minimum age requirement is 25 y/o. We require one parent for every two persons under the age of 25. A PARENT MUST BE STAYING IN THE UNIT AT ALL TIMES.




Outdoor Amenities
  • Beach Chairs
  • Beach and Pool Toys
  • Community Pool
In House Amenities
  • High Speed WiFi
  • Keyless Entry
  • Full Size Washer & Dryer
  • Central Heating & Air Conditioning
  • Hair Dryer
  • Fully Stocked Kitchen
  • Iron & Ironing Board
  • Television
  • SmartTV
  • Linens & Towels Provided (no beach towels)
Kitchen Amenities
  • Microwave
  • Stove & Oven
  • Standard Coffee Maker
  • Refrigerator/Freezer
  • In Freezer Ice Maker
  • Dishwasher
  • Dishes & Utensils
  • Cooking Utensils
  • Toaster
  • Cooking Pots & Pans
Adventures Nearby
  • Bicycle Rentals
  • Fishing
  • Bay Fishing
  • Golf
  • Jetskiing
  • Parasailing
  • Sailing
  • Snorkeling
  • Scuba
  • Surfing
  • Amusement Parks
  • Water Parks
  • Paddleboarding
  • Nature Trail Walking
  • Walking
  • Zoo
  • Aquarium
  • Festivals
  • Harbor
  • Marinas
Leisure Activities
  • Antiquing
  • Beachcombing
  • Birdwatching
  • Horseback Riding
  • Shopping
  • Outlet Shopping
  • Photography
  • Scenic Drive Siteseeing
  • Bowling
  • Miniature Golf
  • Shelling
  • Fine and Casual Dining
  • Church
  • Synagogue
  • Health & Beauty Spa
  • Museums
  • Library
  • Movie Theaters
  • Restaurants
Local Amenities
  • ATM/Bank
  • Grocery Store
  • Organic Food Store
  • Hospital
  • Urgent Care Facility
  • Laundry Mat
  • Massage Therapist
  • Walk In Medical Services
Show All

Season Period Min.Stay Nightly Weekly
2024 12/31/2023 - 12/31/2024 2 $1,000.00


Great stay for family of 15
You asked for a review of our stay at Playing Hookey. The house slept 15 comfortably and we had plenty of room to move around and do what we wanted. The staff was very helpful and prompt. We enjoyed the pool, access to the beach, pool and exercise area. Thank you very much!!!
Sally keating
Dec 2023

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