Holiday rentals with outdoor seating in St. James Plantation

Black Pearl Bungalow - Steps to the beach

Black Pearl is in the top 5% of Airbnbs in nation! Book now for your summer vacation. No parking worries because you’re a short stroll to the beach. Load up the beach cart (provided), and enjoy everything OKI has to offer. Prime location in the highly desirable Yaupon Beach area, Less than 500 steps to the beach. Sit on the screened front porch and listen to the ocean, enjoy dinner alfresco, or relax in the comfort of this beautiful bungalow. Seasonal requirements - Sat to Sat 6/20 - 8/22

Adorable OKI guest suite ~ walk to BEACH!

Come stay at our peaceful guest suite where you can walk to the gorgeous beach in minutes! There’s ample free parking here too! The suite is only half a mile from the closest beach access as well as grocery stores, restaurants, cafes, ice cream shops, bars & parks. Adorable Southport is only 15 min away! Enjoy a day at the beach and then come rinse off in the outdoor shower (w/ hot & cold water). Grill up a meal and enjoy it in the quiet outside guest area. Your relaxing beach getaway awaits!

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!

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.

Charming Oak Island Bungalow - Great Location!

Our 3BR cottage promises a fresh and clean experience that is ideal for your family beach week or weekend getaway. Close to everything Oak Island has to offer - sand, surf, fishing, boating and biking - whatever your heart desires. A well stocked kitchen to enjoy a dinner in or treat yourself to one of the many Oak Island and Southport restaurants. Guests rave about the screen porch with the "Where Have You Been All My Life" hanging bed and the new backyard firepit. Come, relax and enjoy!

Kid & Dog Friendly Stylish Ranch by Middleton Park

Welcome to Sweet Hideaways on Oak Island! This 3-bedroom, 2-bath home features an outdoor shower and a fully fenced yard. Enjoy beach essentials like chairs, umbrellas, boogie boards, and a gorilla cart for an easy trip to the shore. Family-friendly with a high chair, pack n play, toys, playhouses, and a fun custom mural! Just 0.7 miles to the beach and 1 block to the ICW. Walk to Middleton Park and the splash pad in minutes! Conveniently located near restaurants and shops.

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.

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.

Pet Friendly - Home Close to the Beach

Serenity awaits you at this peaceful updated beach themed home. The home has everything you need to enjoy your Oak Island getaway! You’ll want to come back!! Walk to the beach via the 9th St scenic walkway. Enjoy a day at the beach, kayaking, fishing, boating or any of the many activities Oak Island and nearby Southport offers. Enjoy relaxing evenings at home dining with the family, watching tv, playing games or stargazing. Don’t wait, come make lasting memories.

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.

Coastal Comfort: Voted #1 Coastal Community in NC

Welcome to Coastal Carolina in St. James Plantation! Our very private Club Villa Condo is ground level. SJP has been ranked #1 Coastal Community in the Carolinas. Southport was listed in the top 46 best coastal towns in 2017! This rental is beautifully decorated, has a great location & amenities. Just a short walk to the pool and a short drive to the beach. Close to Wilmington & Myrtle Beach.