Holiday rentals in Oak Island

Our Beach Haven OKI- Near Middleton Park

Book today for 2026! NO PET FEES + Fully fenced yard! 7 minute walk to the beach on all sidewalks, near Middleton Park, shops & restaurants, in the heart of Oak Island! This newly updated 3 bedrooms, 2 bath home sleeps 6 and has plenty of space to spread out. Enjoy coffee or cocktails on the private sun porch, cook your meals in the well-stocked granite & stainless kitchen. Beach chairs and buggy included. All linens included with beds made! Need 2 homes, Beauty & The Beach is around the corner.

Charming Beach Bungalow (9-min walk to the Beach!)

Newly renovated, refreshingly colorful, and fully stocked with everything you need for a rejuvenating stay at the beach. Lounge on comfy furniture, stream your favorite shows on large smart TVs, and unwind in a rocker on the brand-new screened-in porch. The spacious kitchen is equipped with new appliances, granite countertops, and all the essentials to enjoy a home-cooked meal with your crew. The home is located in the prime of the island just a 9-minute walk to an absolutely beautiful beach.

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.

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.

Beach Cottage in the Trees, Dog Friendly

🐶 Welcome to our Beach Cottage in the Trees 🌳. A peaceful, dog-friendly haven for everyone in your family. This quaint, cozy “home away from home” is close to the beach (0.2 mi), local shopping, restaurants, and golf course, but in a quiet neighborhood away from the crowds. Beautiful screened-porch among the trees for relaxing, and a spacious back-yard on a wooded lot for all to enjoy. 📝PLEASE read entire listing and ALL rules prior to booking. 🐶DOGS always WELCOME.

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.

Starfish Suite with Steam Spa

Two adults can enjoy a lovely seaside experience at this private suite with outdoor patio. It is on second floor with its own keyless entrance. We are around the corner from Middletown park which offers free summer Friday concerts and Monday farmers market. Other amenities are pickle ball, tennis and basketball courts. Walking distance to some great eateries. Five minute walk to the beach. Wind down after the beach in an aromatherapy. Not child proofed.

Panoramic Oceanfront Views in the Heart of OKI

BookSmart Properties presents: Sunny Side Up! Experience the best of Oak Island at this delightful oceanfront home with direct beach access. This cozy 2 bed/1 bath retreat offers a prime setting for relaxation, featuring a fully equipped kitchen, dining with ocean views, and a welcoming patio that makes you feel right at home. Explore nearby local restaurants, shops, and attractions. Book your stay and create unforgettable seaside memories!

Great Location! Walk to Pier.

Pier Joy is a charming beach cottage nestled in the historic Yaupon area of Oak Island. You can walk to the sand, surf, and iconic Oak Island Pier in less than 10 minutes! Our large fenced back yard is perfect for families to gather around the firepit or play a game of corn hole. We believe dogs are members of the family and gladly welcome up to two in the cottage. This is your place for peace, comfort, and Pier JOY!

Serenity Season

This wheelchair friendly spacious studio apartment has a fully stocked kitchen, queen size Murphy bed, bathroom with a walk-in, wheelchair friendly shower, front loading washer/dryer and private screened in porch; beach towels, beach chairs, cooler and an umbrella are all included with rental. About a 10 minute walk to the ocean and 3 minute walk to the ICW. Our community is very peaceful, quiet.