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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!

Southport Serenity

Welcome to this charming 3-bedroom, 2-bath home just 10 minutes from downtown Southport and Oak Island! Perfect for families or friends, this retreat features an open-concept living area, fully equipped kitchen, and cozy bedrooms. Enjoy the fenced-in backyard, ideal for pets or kids, and relaxing under the glow of string lights in the evenings. Close to beaches, dining, and shopping, it’s the perfect base for your coastal getaway. Book now and experience the charm of Southport and Oak Island!

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!

Beautiful House close to 31st Street beach access

Beautiful Oak Island, NC home nestled in between the beach, Davis Canal and intracoastal waterway is centrally located to kayaking accessibility, paddle boarding, quite walks on the beach through the scenic beach access. The island is filled with local restaurants that never disappoint. The home is cozy with a large front porch with rocking chairs and a side screened porch with gas grill. Beach is just a short walk away over the scenic walkway. Located close to everything! Don’t miss this!

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.

Sleeps 18*1 Block to Beach*2 Master Suite*Gameroom

3-4 min. walk to the beach! 3 night min stay stay June-August 2026. Sleeps 18! Stay at our spacious "American Dreaming" cottage on Yaupon Beach/Oak Island and check off all of your vacation boxes! Sit by the firepit and listen to the sounds of the crashing waves, which are only 1 block away. Head down to the beach during the day and then cool off in our private stock tank pool while your kids play ping pong in the game room. Enjoy a short 10 minute drive down to historic Southport!

Beachfront cottage with views from every room!

Enjoy this slice of paradise, with views from every room and the beach just down the back steps! The home sleeps 6 in 3 bedrooms with one king bed and 2 queens. The master bedroom has the option of closing the pocket doors for privacy, or leaving them open for amazing ocean views. The living space offer an open floorplan, perfect for entertaining. This home is located on the East end of the island between the two bridges that access the island and close to the Ocean Crest Pier.

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.

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.

Cozy Cottage 10-15 min scenic walk from the beach!

~The Captain's Cottage~ Come unplug in this newly built cottage that is the perfect getaway. Two bedrooms, 2 full bathrooms, kitchen, a cozy living room, a fully fenced backyard and walking distance to the beach will provide you with the ultimate vacation. Pet friendly so your furry family members can join in the fun! Plenty of activities in the area, great restaurants, and fun for all ages!