Brand NEW 7 Bedroom, Putting Green, Karaoke Stage, Pool & Hot Tub & Golf Cart!

The Shady Pineapple – Sleeps 22 | Golf Cart | Putting Green | Walk to Beach

Welcome to The Shady Pineapple, a vibrant and spacious beach retreat in the heart of Santa Rosa Beach along scenic 30A. Designed for large groups and unforgettable gatherings, this luxury home offers the perfect blend of comfort, fun, and convenience—with room for 22 guests, premium amenities, and a prime location just minutes from the Gulf.
Sleeps 22 in Comfort & Privacy

This home boasts 7 bedrooms and 7.5 bathrooms, with each bedroom featuring its own private en-suite bath—no sharing required. Whether you’re traveling with multiple families, a group of friends, or hosting a special occasion, The Shady Pineapple’s layout ensures everyone has space to spread out and unwind. Bedrooms include a mix of king suites, bunk rooms, and cozy guest rooms—all equipped with smart TVs and fresh, stylish decor.
Bonus Third-Floor Game & Entertainment Room

On the third story, you’ll find a spacious bonus room designed for fun and relaxation. This entertainment hub features a collection of classic board games, an arcade machine, and even a karaoke stage—perfect for evening competitions or rainy-day fun. It’s a favorite hangout space for both kids and adults.
Free 6-Seater Golf Cart Included

Included with your stay is a street-legal 6-seater golf cart, making beach runs, shopping trips, and dinner outings effortless and fun. Park with ease, carry your gear, and explore 30A like a local.
Private Putting Green and Outdoor Fun

You don’t have to leave home to have a good time. The backyard features a private putting green, outdoor games, and plenty of lounge seating. Grill up some burgers on the gas BBQ, enjoy drinks at sunset, or challenge your crew to a little friendly competition.
Chef-Ready Kitchen and Dining

Cooking for a crowd? The Shady Pineapple delivers. Enjoy a fully stocked kitchen with double refrigerators, high-end appliances, ample cookware, and a large island that makes meal prep a breeze. Gather at the oversized dining table or opt for outdoor dining under the stars.
Prime Location

Situated in a quiet, family-friendly neighborhood, The Shady Pineapple is just a 5-minute golf cart ride or 10-minute walk to the beach. You’re perfectly positioned near local restaurants, shops, and 30A attractions like Seaside, Blue Mountain Beach, and Grayton. Whether you want to lounge by the shore or explore local gems, everything is within reach.
Amenities at a Glance

Sleeps 22 | 7 Bedrooms | 7.5 Bathrooms

En-suite Bathroom in Every Bedroom

Third-Floor Bonus Room with Games, Arcade & Karaoke

Free 6-Seater Golf Cart

Private Backyard Putting Green

Smart TVs in Every Room

High-Speed WiFi

Full Laundry Room

Outdoor Games and BBQ Grill

Beach Towels, Chairs, and Gear

Pack ’n Play and High Chair (upon request)

Driveway Parking for Multiple Vehicles

Perfect For:

Family Reunions

Multi-Family Getaways

Wedding Groups

Retreats and Corporate Stays

Golf and Beach Vacations

Why Guests Love The Shady Pineapple
Each bedroom has its own bathroom
Bonus third-story game and karaoke room
Walk or ride to the beach
Fun, private backyard with putting green
Bright, stylish, and spotless
Designed for large groups and unforgettable memories

Don’t miss your chance to stay at The Shady Pineapple, one of 30A’s most group-friendly and amenity-rich vacation homes. Book now and get ready to relax, reconnect, and enjoy everything Santa Rosa Beach has to offer.

***Additional fee applies to heating pool of $300 per stay***

***Must sign rental agreement and waivers within 2 days of booking***