Holiday rentals with a kayak in Oak Island

Howells Point water view, pier

Relax with the whole family in peaceful Sunset Harbor. Enjoy fishing & swimming, Kayaking, biking, waters sports and lots of relaxing in this quiet & safe neighborhood. Get off the main path and enjoy your time in this beautiful home with gorgeous views of ICW. Brew a cup of coffee and step out on the screened porch for a beautiful sunrise, and in the evenings gather with the locals at the boat ramp & watch the sunset. Enjoy the private pier. Minutes away from Oak Island, Holden, Southport.

OKI Beach Retreat - Relax, Bike, Walk to Beach

Welcome to Jolly Roger Retreat in OKI! Our family-friendly beach house features 3 BR, 2 BA & an outdoor shower. Enjoy a large dining table for meals and game nights, and relax on the screened-in porch or patio. Outdoor activities include bikes, basketball, horseshoes and bocce ball. Just a 10-min walk to the beach, we provide beach toys, chairs, & a shade structure. Located in the heart of OKI - walk to restaurants, mini-golf, ice cream & activities. Perfect for creating lasting family memories!

Clara Vista-Waterfront Home, Pier, Deep Water Slip

Take it easy at this unique, tranquil getaway! Clara Vista overlooks a bend of Davis Canal, with its salt marsh and winding channels. Try spotting the various birds wading at creek edge or dolphins feeding. Moor your boat on the dock and enjoy some of the best fishing on the island from your private pier! Your vacation home is the top floor of a duplex , with 3 bedrooms , 2 bathrooms, full kitchen, open dining/living room, outdoor shower, fire pit, outdoor grill and a large front porch.

Easy 7 minute walk to the beach!

Nestled on a quiet & wooded side street, this dog friendly 3 bdrm / 2 bath elevated beach house is a quick 7 minute walk to the beach, offering the perfect mix of nature and coastal fun. House features an open concept living/dining area with gas logs, large screened porch, fenced yard, Jacuzzi bathtub, gas grill, firepit, outdoor shower, 2 kayaks, 3 beachcruisers, badminton set, beach chairs/toys, high speed wifi, Smart TVs in every bedroom, and a separate teen hangout area in the garage.

Mai Tai Good Time-Kayaks, Bikes, Fenced in & more!

Come have a "Mai Tai Good Time" with the whole family at this cozy beach cottage just a 5min drive from Holden Beach! The large fenced backyard is very private, has outdoor seating, and is perfect for kids and pets! Plenty of beds to bring friends or for multiple families, HUGE outdoor shower, and a fire pit. We keep the wood stocked for you! We have bikes, beach chairs, lawn games, and kayaks to use during your stay. Even enough space to park your boat for joy riding or fishing!!

Scenic Getaway with Pool & Hot Tub

Add some peace and tranquility to your trip...beautifully furnished on the inside, fully stocked house, with an oasis of a backyard - this is a home you'll want to visit again and again. With your own HEATED saltwater pool & hot tub, in a private backyard paradise...you may not ever want to leave the property. Minutes away from the beach, steps away from the Intracoastal Waterway, and one street over from the scenic beach walkway, this house will not disappoint.

Large Home wGuest House•Kayaks•Fire Pit•Lawn Games

Wake up to boats gliding along the Intracoastal Waterway, coffee on a breezy deck, and the rhythm of island life all around you. The Yacht House is a curated stay on exclusive Yacht Drive with a large yard, fire pit, BBQ, hammock, lawn games, ping pong, and kayaks. The home has 5 bedrooms, including a private guest suite with its own entrance, living area, and kitchen. Comfortably sleeps up to 10 adults + 6 kids. Just 3 minutes to the beach down Middleton!

Cottage under Oaks, quiet street w/ dock, Kayaks

We found our favorite NC beach town. Oak Island's uncrowded beaches are just a 2 minute drive or 15 minute walk away. Walk to the dock at end of the street to fish or read or launch your kayak to explore the historic intracoastal waterway and end your day watching the sun set over the water. Come experience the beauty of Oak Island in this spacious refurbished cottage under the most beautiful twisted oaks on a quiet street on the friendliest little island.

300 Steps To The Beach - Stone’s Throw Bungalow

Book now for spring and summer! Easy beach access with no parking worries! Amazing location (literally 300 steps to the beach). Stone’s Throw Bungalow has been newly renovated. Pristine home is perfect for your family! One level living. Situated in the Yaupon area, it’s on the water side of the island with direct beach access. Beautiful oaks canopy the porch. Seasonal requirement 6/7-8/23 Sat to Sat only.

Ocean front,pet friendly,fenced yard

Welcome to “The Boys of Summer Rentals,” a favorite oceanfront escape with direct beach access and a fresh new feel. Unwind with sunset views from the deck, enjoy fast WiFi and smart TVs, and walk just minutes to shops, dining, and groceries. Step straight from your fenced yard onto the beach—perfect for kids and pets. Soak in unforgettable sunsets from the spacious sun deck or relax on the covered porch.

Great Marsh View & 2 Blocks to Beach-LongStayDscnt

Escape to Oak Island's tranquil shores and the serenity of the marsh at The Hammock House. This 2-bed, 2-bath haven is surrounded by picturesque marshlands with breathtaking views and the ocean waves just 2 blocks away. Grill out and dine al fresco, relax in the hammocks or lounge in the super comfy living room after a long day at the beach. Enjoy the peace and quiet of the Carolina beaches.

6BR Beachfront PrivPool (heat opt) HotTub Elevator

*BEACHFRONT*6BR 5.5 BA*PRIVATE POOL (heat available)*HOT TUB*ELEVATOR*FIREPLACE* Welcome to our family's piece of paradise: the Blue Barracuda! We've designed the perfect space to create cherished family memories and comfortably house large families & groups. 2026 is booking fast but we still have Aug 22-Sept 5, Thanksgiving and Christmas open.