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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!

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).

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.

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.

Air Cottage @ Bald Head Island

"Air" is a charming cottage located on the Bald Head Marina & the perfect home on BHI for a couples getaway, nomad traveler, or businessperson looking to enjoy the WFH lifestyle from a beach chair. Hi-speed Internet makes it easy to stay connected while taking in the views of the ocean and marina, or get out and enjoy nature. 5 min walk from Bald Head Island Ferry Terminal, restaurants, shops, rentals **Golf cart is included** **Shoals Club access available for additional fee**

The Sunsetter - Surf studio with private roof top

The Sunsetter sits right across the bridge onto Wrightsville Beach overlooking Banks Channel and is just steps from the beach.  It has been uniquely renovated with one of a kind finishes and tasteful interior design, paying homage to the building's history while bringing it up to date with a Malibu surf style feel!  It has quickly become one of Wrightsville Beach’s most exclusive stays with its biggest attraction being the nearly 800sq.ft. fully turfed private rooftop deck.

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.

The Bungalow Loft

A classic 1946 duplex cottage on the outside, reimagined as a modern coastal retreat on the inside, The Bungalow Loft blends timeless charm with contemporary comfort. This thoughtfully designed space features one bedroom, two additional daybeds in the living area, a full bathroom, a well-equipped kitchen, and a cozy dining nook. Step outside to enjoy expansive outdoor living, complete with a front porch, spacious deck, fire pit, and refreshing outdoor shower.

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.