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.

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!

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.

Prime OKI location; walk to 43rd St beach access

Welcome to our Coastal Oasis! Our space is 3 bedrooms (4 beds+ pack and play+ bassinet), 2 bathrooms, outdoor shower, extra large screened in front porch and back deck with dining area and grill. Our home caters perfectly to families (including those with infants and children) and everyone in between! Between lounging on the front porch (rocking chairs, egg chair, and couch set) or listening to music while grilling out back, we hope your time here is nothing but happy memories and fun times!

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.

Above the Tide | *10 Min Walk to Beach* + Bikes

Sunshine & waves awaits you and your family! This cozy home has everything you need for your vacation get away. Only a short walk down the Scenic Walkway to the beach (10 min). Fire pit, picnic table, patio area out back w/ outdoor grill, and outdoor shower. There is also Wi-Fi and 3 TVs. Fully stocked kitchen with all your cooking necessities. Beach Extras: - 4 adult bikes - Shibumi Shade tent - wagon - multiple chairs - coolers - variety of toys/games for your days down 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 & 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.

Escape to the Cape On the Gorgeous SPT Waterfront

Located on the beautiful Southport Waterfront you'll enjoy a well-appointed gem located within the RiverHotel of Southport that includes a small balcony with views of the Cape Fear River, guest pool, and private beach exclusively for our guests. We also have a huge deck with lots of tables and chairs to enjoy the spectacular water views! Covered parking is available within steps of the elevator. Make your Southport vacation memorable! Escape to the Cape awaits you!

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.

Scenic Getaway with Pool & Hot Tub

Add some peace and tranquility to your trip...beautifully furnished on the inside, fully stocked house, with an oasis of a backyard - this is a home you'll want to visit again and again. With your own HEATED saltwater pool & hot tub, in a private backyard paradise...you may not ever want to leave the property. Minutes away from the beach, steps away from the Intracoastal Waterway, and one street over from the scenic beach walkway, this house will not disappoint.

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.

Southport Tree Escape - King Treehouse Downtown

“Perfect for two. Easy access. Very quiet.” – William, ‘25 Escape to your private vaulted studio nestled in the trees — the perfect setting for a romantic getaway or peaceful weekend retreat. Hosted by year-round locals, this charming guesthouse blends contemporary comfort with the relaxed feel of small-town Southport. Perfect for two guests seeking a quiet retreat close to downtown and the waterfront.