Family-friendly holiday rentals in St. James Plantation

🐶 BOW•WOW🐾 BEACH•BUNGALOW™🏖 🏠Cozy & Dog Friendly🐶

🐶 Welcome to the BOW•WOW Beach•Bungalow™ 🏖. A peaceful, dog-friendly haven for everyone in your family. This quaint, cozy “home away from home” is close to the beach (1/3 mi), local shopping and restaurants, but in a quiet neighborhood away from the crowds. Beautiful screened-porch for relaxing, and a very spacious fenced-back-yard on a double-lot for all to enjoy. 📝PLEASE read entire listing and ALL rules prior to booking. 🐶DOGS always WELCOME. 💲DISCOUNTS for all WEEKLY and MONTHLY bookings.

Indoor spaces · Family · Sleep quality

Surf Break Bungalow

Take a break and unwind at this cozy Beach Bungalow! The Beach Bungalow is decorated with warm tropical colors and hints of a surfing décor. This is the perfect getaway to hang out with family, friends, or just to escape crowds. Follow the sound of the waves gently crashing on the shoreline and within minutes you will soon be dipping your toes in the sand. A private corner lot with easy parking access. Also, the perfect location to hang on the screen porch or relax in the shaded hammock.

Kitchen · Indoor spaces · Air conditioning

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.

Indoor spaces · Family · Outdoor spaces

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.

Family · Kitchen · Comfort

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!

Kitchen · Family · Pets

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!

Kitchen · Indoor spaces · Getting around

Oak Island Oceanfront – Top Floor 2BR Condo

Enjoy a perfect oceanfront family getaway on Oak Island's West Beach. This 2nd level unit of our beach house has separate entrance, two bedrooms, one bathroom, and sleeps six guests. The kitchen is fully equipped with pots, pans, utensils, full size fridge, microwave, stove/oven, and dishwasher. Enjoy sunrises and sunsets on the huge deck watching the waves and the occasional dolphins. If your dates are not available, please check out our 1st level unit availability at www.airbnb.com/h/oki1

Family · Kitchen · Access

Newly Built Coastal Cottage - Clean, Modern & Cozy

Our newly built, immaculately clean three-bedroom cottage is the perfect place to relax and enjoy everything OKI has to offer. Located just 0.4 miles from the beach, you’re an easy walk or bike ride away from the sand, plus close to local shops, and great restaurants. Your stay includes free linens, along with beach chairs, sand toys, bikes, boogie boards, and a Shibumi Shade to make beach days effortless. You’re close to everything - including the charming waterfront town of Southport.

Family · Kitchen · Parks

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!

Family · Indoor spaces · Pets

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.

Family · Kitchen · Decor

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.

Indoor spaces · Family · Decor

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.

Indoor spaces · Kitchen · Walkability