Family-friendly holiday rentals in Oak Island

Ocean View/Pup Lovin’/Steps to Beach/King Bed!

When ordinary vacations just won’t cut it, one destination will change everything you thought you knew about relaxation & hospitality. In a world of run-of-the mill rentals, comes an experience that defies expectations. Prepare yourself for a vacation that will make your Social media viewers question their life choices.  Critics are saying: “They have put so much thought into the details of this home” “Amazing experience!” Book now for a stay that will ruin all other vacations forever. 

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.

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.

Cheers! Waterway Beach Cottage

Relax peacefully and have fun with the whole family. With the ICW in your back yard you can sit, fish on the longest pier on the island, work(if you must) with availability to charge devices or just relax and have a beverage watching the sun set. Just minutes from the beach, walk or take the golf cart for a day of fun in the sun. After a long day grab some takeout or cook in the fully furnished kitchen and dine on one of the tables outside or inside and watch the boats go by on the waterway.

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!

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.

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.

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.

1960's Ocean Front Cottage

1960's vintage ocean front cabin. Pine paneled interior with vaulted ceilings. Easy upkeep. Three bedrooms that sleep six (king, full, two twins) with one blowup mattress and portacrib. Two full baths and one outdoor shower. Original kitchen cabinets. Bar seats 6. Pod and Mr. Coffee makers, blender, toaster oven, microwave, crockpot. Large front deck overlooking ocean with adjoining side deck. Very private. No houses on second row. Great fishing!

Oceanfront-pvt access-dog friendly-Incredible Ibis

Sandy shorelines are calling you to this 3-bedroom, 1.5-bath vacation cottage on Oak Island! This beachfront property will leave you relaxed and rejuvenated. Panoramic ocean views from the deck! Our home offers a getaway that invites you to surf the waves, perfect your tan, and catch up on your favorite book while digging your toes in the sand. Featured in the Fall 2021 Hallmark film "One Summer." Enjoy a moment now!