Family-friendly holiday rentals in Bald Head Island

Whimsy Whale Cottage, Oceanview, Fenced Yard

We’d love for your happy beach memories to be made here at our cottage by the sea, The Whimsy Whale. Our island cottage is perfectly placed under a canopy of magnificent live oaks, about 300 steps away from the ocean. Nestled on a quiet beach access street, central to all the best attractions, shopping and eateries on Oak Island; close to attractions in Southport. It is one of our favorite places to spend time together and we look forward to sharing it with you, your loved ones and friends.

Happy's Place Downtown Southport

This is my uncle Happy's place. It is in historic downtown Southport. Walking distance from restaurants, shopping, and the Cape Fear river. Located on a quaint alley just off the Main Street of town. This happy little cottage is nestled amongst large live oaks and in the shadow of Southport's iconic water tower. The home has one bedroom with a queen bed. The living area has a twin bed and two chairs. There is a full kitchen and small bathroom. Southport’s beautiful waterfront and parks await.

Rise and Shine! Beach, pool, & amazing views!

Welcome to RISE AND SHINE at Oak Island Beach Villas! Fabulous location on tranquil Caswell Beach. Close to amazing food, the iconic Oak Island Lighthouse, and top rated golf yet you feel the peaceful vibe of being on the east end of the island. Steps from the beach with breathtaking views, this beautifully decorated condo features 2 bedrooms, 1 bath and sleeps 5-6. Choose a short walk to the pool (seasonal) or simply relax on the private balcony listening to the soothing sounds of the ocean.

Luxe & Family Friendly - Kayak Our Dock, 2 Clubs

Relax in our cozy, modern home tucked in the woods of Cape Fear Station. Kayak from our private community dock, go crabbing, swim at either of the club pools or take a quick golf cart ride to nearby East Beach! Stylish & comfortable, this home has been fully renovated and outfitted with family-friendly, thoughtful amenities to elevate your vacation and help you pack a little lighter! Have a question about our home or need something important for your stay? Let me know, I'd love to help!

The Surf Shack at BHI: 2Br East Beach cottage

Welcome to the most magical little island. The Surf Shack at BHI is the best place for your family and friends to experience the magic of Bald Head Island. With 2 bedrooms each with their own bathroom, it is perfect for 2 couples or a family with children. Located in the tranquil neighborhood of Surfman's Walk, it is only a short bike ride or golf cart to East Beach and Shoals Club. Enjoy your morning coffee on the porch, ride to the market for coffee, and spend your days at the beach.

Cozy BHI Condo - Community Pool and BHI Club

Welcome to "Marooned Five". We enjoy sharing our home so others can experience the beauty and magic of Bald Head Island. Our home has 2 bedrooms, 2 full baths, fully stocked kitchen (renovated March 2024 and 2022!) & a spacious loft for the kids. Located in Royal James Landing, a private pool and picnic area are available for use just a few steps away. There are 6 bikes (4 adult/ 2 child) & 2 4-person golf carts. Guest memberships for the BHI Club are available for an additional fee.

The Coastal Coconut: Beautiful Ocean View Condo

This spectacular ocean view condo with top notch 2022 renovations is just steps from the beach. Be swept away by the view of the rolling waves, whitecaps, and the OKI Pier as you relax and enjoy a beverage on the balcony. You will also be treated to a breathtaking sunset as the colors change each minute across the sky. Retire to the living room and rest your tired feet on a comfy sectional sofa as you interact with others in an aesthetically pleasing open floorplan setting.

Captain's Cottage: The heart of downtown Southport

Step into history without sacrificing luxury at the Captain's Cottage! Located blocks from the water on one of the first 100 lots in Southport, is a beautifully furnished coastal cottage. The home boasts a commercial quality kitchen, spacious rooms throughout, and two cozy porches overlooking Historic Franklin Square Park. The location is ideal within walking distance of all that Southport has to offer and is a short drive to several beaches.

Oceanfront Incredible Ibis w private beach access

Sandy shorelines are calling you to this 3-bedroom, 1.5-bath vacation cottage on Oak Island! This beachfront property will leave you relaxed and rejuvenated. Panoramic ocean views from the deck! Our home offers a getaway that invites you to surf the waves, perfect your tan, and catch up on your favorite book while digging your toes in the sand. Featured in the Fall 2021 Hallmark film "One Summer." Enjoy a moment now!