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.

Location · Getting around · View

River Road Retreat - Heated Private Pool, Pond, Fi

Private pool, pond views, gardens, and a 10 minute drive to the beach! This home backs up to a nature preserve. Relax by the pool and tiki bar area watching TV or enjoying music. Pool Heater: Our pool is open and maintained year round. The pool heater can reliably generate heat as long as the outside temperatures are above 50 degrees which will generally be from March to November, however in our area it is not unusual for us to have warm days at any time of year. Many vacation rental propert

Location · Outdoor spaces · TV

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!

Outdoor spaces · Location · Family

Guest Suite with Games Room, BBQ, Kayaks/Surfboard

Welcome to the Guest Suite at The Yacht House! Ease into relaxed island living. Across from the Intracoastal Waterway, this ground-level 1BR/1BA guest suite is near Veterans Park for fishing and waterfront picnics. Drive to the beach in just 3 minutes via Middleton, stroll over the pedestrian bridge to the beach (20 minute walk), or launch a kayak nearby and explore at your own pace. ✦ Beach gear ✦ Baby gear ✦ Laundry room ✦ Patio ✦ BBQ ✦ Lawn games ✦ Hammock ✦ Fire pit ✦ Table tennis ✦ Kayaks

Location · Kitchen · Checkout

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!!

Outdoor spaces · Location · Comfort

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.

Location · Value · Checkout

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.

Outdoor spaces · Location · Getting around

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.

Location · Outdoor spaces · Parks

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.

Value · Location · Comfort

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.

Location · Outdoor spaces · View

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.

Outdoor spaces · Location · Condition

Lovely Little Beach Guest House

Our guest house is a 650 sq. ft. studio apartment over our detached garage, and only 300 steps to beautiful Kure Beach. It's perfect for a long weekend, a relaxing week at the beach, or an extended winter get-a-way for snowbirds. You'll love the ocean breezes and starry nights. Ask us about our monthly rate for Dec., Jan., and Feb.

Value · Location · Layout