
Holiday rentals with a kayak in Pleasure Island
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Top-rated Accommodation with a Kayak in Pleasure Island
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.
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Holiday House Rentals with a Kayak

A Salty Beach HGTV Featured Home
We loved the place during our stay! Home was very clean, and bright. It was the perfect place for my mother and I to bring my two girls and their friends for their 17th and 14th birthdays! Perfect location to the beach right across the street. Chris had a TON of beach chairs, buggy, gear for the beach which was so appreciated. He was very responsive and super helpful.

Ocean Vibes on the ICWW. w/pier and on peninsula
Wonderful place! The sandbar was the most amazing part! We loved kayaking around and swimming! We will be back for sure!!

ICW views! Linens/kayaks/bikes included.
fantastic location, close to everything. Great space for a large family. and right next to the sound.

Oak Island Home w/ Yard < 1 Mi to the Beach!
Great weekend stay. Close to the beach, Southport and Bald Head Island. Host was very responsive and attentive. Our daughter even forgot an item that they found and sent back to us!

Charming Dog-Friendly Apartment
Very clean and very comfortable. The host was very helpful and accommodating. The location is an easy 15 minute deive to the beach. I thought the renatal space might have some beach gear like an umbrella or towels but did not. I would recommend to others.

Great Marsh View & 2 Blocks to Beach-LongStayDscnt
We loved the hammock house! It was so peaceful and beautiful. It was also very convenient to be able to walk to the beach easily and there were amazing restaurants and plenty to do nearby. We will be back!

Luxe & Family Friendly - Kayak Our Dock, 2 Clubs
Five Stars All the Way! We had the most incredible stay at Vaycash on Bald Head Island! From the moment we walked in, it felt less like a rental and more like staying at a dear friend’s beautiful home. Stef has thought of everything—the home is gorgeously decorated, full of charm, and stocked with more amenities than any place we've ever stayed. This was hands-down the most above-and-beyond experience we’ve ever had with an Airbnb. Every detail was thoughtfully done—from the fully equipped kitchen (a dream to cook in!) to the peaceful, tucked-away location in the woods that gave us the perfect mix of relaxation and adventure. The golf cart made exploring the island a breeze, and the kids were thrilled with the bikes and kayaks. Stef’s generosity and attention to detail made this getaway truly special—we didn’t want to leave! We can’t recommend Vaycash highly enough and are already dreaming about our next visit.

Super Contemporary Beach House for family fun!
We had a little family reunion here and the house accommodated us perfectly. There were plenty of beds, living space and things to do for all the ages. The kitchen and outside grill had everything we needed. We only went out to eat once! There was everything you could possibly need for the beach or inlets! It was the perfect vacation home!
Cottages with a kayak

Cottage under Oaks, quiet street w/ dock, Kayaks
We had such a wonderful stay at this cozy vintage beach cottage! Tucked away on a quiet, peaceful street, it was the perfect retreat for a relaxing getaway. The welcoming front porch was a favorite spot to sip morning coffee and enjoy the breeze. Inside, the cottage has a charming coastal vibe with vintage touches that add character and warmth. It’s clear that a lot of thought went into making it both stylish and comfortable. The space was clean, well-kept, and incredibly well-supplied with everything we needed—from kitchen essentials to beach gear. If you're looking for a place with personality, tranquility, and easy access to Oak Island’s beautiful beaches, this cottage is a fantastic choice. We’d definitely come back!

Newly Renovated Cottage on a Tidal canal
Beautiful home and a very convenient location. The house was very clean and had everything we needed.

Charming Wilmington Cottage - Walk to Downtown!
This was our second time staying at this house. It’s very comfortable, beds have great mattresses, kitchen has everything you need. The walk to town is safe and easy. Savoir Latin restaurant is 5 minute walk, fabulous food. Highly recommend this location. Tucked away from traffic, driveway parking and relaxing front porch.

The Surf Shack at BHI: 2Br East Beach cottage
Perfect place for our 20th Anniversary get away. Loved the house. Comfortable bed! Wonderful stay. Will definitely stay here again. Friendly host who got back promptly.

Georgia On My Mind, Family Cottage
This is a beautiful home. We really enjoyed our stay. This home is in a beautiful neighborhood. Everyone was very friendly. Short walk to the beach and canal. Golf cart is definitely worth having as everything you would want to do is just a short ride and offers free parking. Home is equipped with everything you would need. Very clean and private. Great if you have kids. Homeowner is great as he always responded quickly to any questions I had prior to our arrival. Once you are there, the detailed instructions provided will guarantee a great stay. Definitely recommend and hope to return again.

Cozy cottage
We loved our stay here! Such a cute and comfy cottage, perfect for a beach trip; it comes stocked with pretty much everything you could ask for. Loved that it was walking distance to so many shops and restaurants, as well as beach access points, while also being tucked away down the street for a peaceful and quiet night's sleep. Todd was an excellent host as well, very friendly and responsive. Thanks so much!!!

Coastal Country Cottage
We had such a lovely stay at the Tew Cottage! Conveniently located near your beach of choice and downtown areas. The cottage was spotless and well decorated, we felt right at home. Sharlene is a wonderful host and was extremely kind and attentive. We will definitely be back!
Destinations to explore
- Cape Fear River Holiday rentals
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- Sea Gull Public Beach Access
- South Beach
- Seahorse Public Beach Access
- Wrightsville Beach
- Jungle Rapids Family Fun Park
- Cherry Grove Point
- Futch Beach
- Carolina Beach Lake Park
- North Carolina Aquarium at Fort Fisher
- Airlie Gardens
- Long Beach
- Salt Marsh Public Beach Access
- Rivers Edge Golf Club and Plantation
- Hawaiian Rumble Golf & Batting Cages
- Surf City Pier
- Soundside Park
- East Beach
- Bay Beach
- Pelican Public Beach Access
- Tidewater Golf Club
- Oak Island Lighthouse
- Cape Fear Country Club
- Sea Haven Beach
- River Hills Golfs & Country Club