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.

Indoor spaces · Kitchen · Checkout

Sail4fun

Very nice location. Easy walk to the beach. Access #31. View from upper deck is much better than photos indicate. 2 spacious bedrooms Main br with queen and bath. Second br with queen, bunk beds and bath. Large great room, 1/2 bath, and totally updated kitchen and washer/ dryer . 2 golf carts provided plus 4 bikes. I have memberships in both the Shoals and BHI clubs so a temporary membership in either is available. For separate purchase. There is a no pet policy JUNE6-Aug 14 SAT TO SAT ONLY

Kitchen · Family · View

Southport's Canary Cottage

Southport's Canary Cottage is a newly renovated southern, cottage located in a small, historic town along the Cape Fear River! Canary Cottage is located 1 mile from Southport, 2 minutes from the ferry's at Deep Point Marina & 20 minutes to the Oak Island beaches! While in Southport, enjoy the shops, the majestic Live Oaks, dine at fabulous cafes & restaurants with water views, take a carriage ride, watch the boats go by, go on a ghost walk or tour a museum. Southport has something for eveyone!

Family · Indoor spaces · Amenities

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.

Indoor spaces · Kitchen · Check-in

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 town's main street, this happy little cottage is nestled among 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.

Indoor spaces · Family · Wi-Fi

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 & a loft for the kids. Located in Royal James Landing, a private pool and picnic area are available just a few steps away. Our condo is accessible by stairs on the 2nd floor. 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.

Kitchen · Family · Comfort

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.

Indoor spaces · Family · Cleanliness

Bald Head Breeze

Beautifully updated villa (#34) with premier views overlooking the golf course and just steps away from beach access #13 and the BHI Club. Comes equipped with one 6 passenger golf cart. Bikes are provided. Pet friendly for one dog. This is a 3 bedroom, 3 full bathroom villa with 1 king, 1 queen, and 2 bunk beds. Pack n’ play and high chair available. BHI guest club membership is available for separate purchase. Please contact the club directly for purchase of the guest passes.

Family · Kitchen · View

The Coastal Coconut: Beautiful Ocean View Condo

This spectacular ocean view condo with top notch 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.

Family · Indoor spaces · Getting around

Marshfront Sunrise Views • Dock• 2 Carts• Kayaks

Marsh Dreamin Wake up to one of the most peaceful marshfront settings on Bald Head Island. Marsh Dreamin is a 4-bedroom waterfront retreat with sunrise views, direct dock access for kayaking and crabbing, two 4-passenger golf carts, and an easy walk to Old Baldy, the marina, and West Beach. Thoughtfully stocked and designed for a seamless stay, ideal for families, couples, and returning Bald Head guests who want nature, comfort, and convenience in one place.

Kitchen · Family · Condition

Captain's Cottage | Historic | Walkable

Wake up to park views from rocking chair porches in one of Southport's most iconic homes — a beautiful coastal cottage on the first 100 lots. Steps from the waterfront, shops, and restaurants. The home boasts a commercial quality kitchen, unique touches 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.

Kitchen · Indoor spaces · Decor

A Bird House - special gem on Bald Head Island

Welcome to A Bird House, a beautiful 4 BR, 3 Bath island home on exclusive BHI. A Bird House perfectly accommodates 8 (1 K, 1 Q, 7 twins which includes bunk room for the kids). Plenty of room in the house to perfectly handle two families. Notes: while A Bird House sleeps 11 people, she is best suited for two families with 4 adults and 4 kids. There is a house being built nearby, crew hours are limited by contractor ferry and evenings were quiet.

Family · Indoor spaces · Sleep quality