Holiday houses in Caswell Beach

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.

Oceanfront 2 BR/2.5 BA Condo

Come enjoy our townhome in the Oak Island Beach Villas #206 located on Caswell Beach! Lounge on the oceanside deck incorporated into the living room, or enjoy a private balcony off the main bedroom upstairs overlooking the Atlantic Ocean! Make the most amazing memories watching the dolphins, observing the sea turtles lay their eggs, and watching the most amazing sunsets/sunrises you'll ever see. This condo is right across from the golf course. This is by far the most beautiful beach ever!

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.

Hydrangea Hideaway: A 2 block walk to the beach!

Just 2 blocks to the beach, our vintage Oak Island home has been fully updated and is the perfect space to get away from the every day and find your own island oasis! In the desirable Yaupon Beach area and a 5 minute walk to the beach, a par 5's distance from the Oak Island Golf Club & a few doors down from a bakery & wine shop. Beach gear included, plus a hot water outdoor shower. Hydrangea Hideaway is waiting to welcome you to your Oak Island home! Long term rates available in off-season!

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.

3bd 2b cottage w/Elevator-5min golf cart to beach

Playa Linda Cottage is a brand new spacious 3 br 2 ba home with an Elevator, that is perfect for bringing up groceries, luggage and personal items. The home is located in a quiet street with easy access to uncrowded beautiful sandy beaches. Our cottage is on stilts with a single level open floor with modern amenitites. Beautiful beach decor to help you relax and unwind. Ideal for family getaways, vacationing with friends, or family gatherings. Golf Cart available for an additional fee.

Panoramic Ocean Views, 2 Pools, Huge Deck, Golf!

Your vacation awaits at this tranquil retreat on Caswell Beach, Oak Island! Embrace the serenity as you wake up to breathtaking ocean views and the gentle lull of waves. Recently renovated, this 3BR/2BA condo boasts an expansive deck, offering ample room for your family to relax and recharge. Just steps away lies a secluded beach with shallow waters, perfect for endless playtime with the kids. Take advantage of the nearby community pools and adjacent golf course for even more enjoyment

Charming 60s Bungalow 3 Min Walk Beach Wine Shop

Includes: 2 bikes, beach wagon, chairs, umbrellas, towels, and blankets. Have fun with the whole family at this stylish, charming mid-century cottage! Drop your bags and head to the beach! This unique mid-century charmer is perfectly situated on a quiet street with ocean access at one end and the Intracoastal Waterway at the other. This cottage offers the best Oak Island living, just a 3-minute walk to the beach, local restaurants, shops, and more. Shibumi rental option via QR code..

Free bikes! 5 min walk to the beach! Sleeps 8!

Your family will be close to everything when you stay at this centrally-located beach cottage. Just a 5-7 minute walk to the beach & a quick bike ride to shops, food, & golf. Spend your days at the beach &evenings relaxing on one of the four decks. Dogwood Cottage features TV's in every room, washer & dryer, outdoor furniture, 1 Gig internet, beach bikes, wagon, beach chairs, a cooler, & beach toys. No smoking property. No smoking anywhere on the premises. Vaping is allowed.

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.

Oak and Tide Guest Suite

Renovated Master Bedroom Suite with shiplap walls, whirlpool tub and bidet toilet. Very Spa like and perfect for the single or couple that want to get away. Easy walk to beach., farmers market and outdoor concerts . Walking distance to eateries Your room has its own entrance on second story. Large screened in porch also yours to enjoy! We have Roku TV . New bedroom furniture and mattress with adjustable bed . Not set up for children safety.