Holiday rentals with outdoor seating 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.

Downtown Sunshine Cottage and Golf Cart

Charming, renovated cottage, just blocks from downtown. Ride the 6 seat golf cart to shops, waterfront swings, live music, riverfront dining, and spectacular sunsets. Only a 15 min car ride to Oak Island’s beaches & golf. Unwind in the gazebo, play bocce, or snuggle up for a movie by the fireplace. Sleep soundly in plush queen beds. Enjoy a clean kitchen with Keurig & lattes. Three smart TVs, 1.5 bathrooms and washer/dryer. Must be 24+ yrs old to book. (Signed waiver requested after booking).

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.

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.

Southport’s Southern Charm

Quaint coastal condo located close to all Southport has to offer. This 1 bedroom 1 bath condo right on the main street of Southport! You’ll have a restaurants, shops, and bars within easy walking distance! The large balcony, with covered and uncovered areas has large palm trees and a good view of Howe St. You’re only 6 blocks from the water! The condo comes with everything you could ever need. Wine, snacks, and coffee come standard. Come see why Southport is our “Safe Haven”!

Oak Island Beach Guest Cottage

If you love being a short walk to the beach this place is for you! . We provide beach chairs and a cart for your 5 minute walk to beach. Eat in kitchen and you can serve your honey breakfast in bed. Farmers market around the corner in the summer months as well as concerts every Friday night, Tennis courts, pickle ball and splash pad in the same area to cool you off. We offer Wi-Fi and Roku. . Gas fire place on back porch. Indoor fireplace use is seasonal.

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!

Great Marsh View & 2 Blocks to Beach-LongStayDscnt

Escape to Oak Island's tranquil shores and the serenity of the marsh at The Hammock House. This 2-bed, 2-bath haven is surrounded by picturesque marshlands with breathtaking views and the ocean waves just 2 blocks away. Grill out and dine al fresco, relax in the hammocks or lounge in the super comfy living room after a long day at the beach. Enjoy the peace and quiet of the Carolina beaches. LONG STAY DISCOUNT Dec-March $2,500 plus taxes and fees. Send us an injury.

Stones Throw to downtown Southport

Welcome to our gorgeous 1 bedroom/ 1bath home away from home! These roomy accommodations are just steps from the Southport Marina and in the heart of historic Southport. You have at your disposal boat parking, outdoor pool area, and walking access to Southport's many charms, such as fine dining and shopping. Bikes and beach chairs are in the closet in the covered parking. Your relaxation begins with easy self check-in and keyless entry! Enjoy your stay.

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.

No Cleaning Fee! New Condo w/ Waterfront Pool

Visit the most adorable seaside village! Southport, with it's picturesque waterfront, fantastic restaurants, and adorable shops, has something for everyone. When you feel like staying closer to home, the pool will be calling your name for soaking in the sun while watching the ships sail by, and your private balcony is the perfect spot to sip a cup of coffee while watching the sunrise over the water.