Cottage holiday rentals in Pleasure Island

Whimsy Whale Cottage, Oceanview, Fenced Yard

We’d love for your happy beach memories to be made here at our cottage by the sea, The Whimsy Whale. Our island cottage is perfectly placed under a canopy of magnificent live oaks, about 300 steps away from the ocean. Nestled on a quiet beach access street, central to all the best attractions, shopping and eateries on Oak Island; close to attractions in Southport. It is one of our favorite places to spend time together and we look forward to sharing it with you, your loved ones and friends.

Location · Value · Sleep quality

Surf4life Oceanfront Beach Cottage

One of the last few Direct Oceanfront beach cottages left in CB. Great for small families. Sit on the front porch and watch waves or a beautiful sun rise. This home was owned by the same family for 50 years! While the cottage is small, it offers an excellent beach retreat that is reminiscent of simpler times. Excellent beach and surf break in front of home which is only 100 yards from the Tiki bar! There is also a private beach directly in front of the house. A beach experience like no other!

Location · Family · Checkout

Southport's Canary Cottage

Southport's Canary Cottage is a newly renovated southern, cottage located in a small, historic town along the Cape Fear River! Canary Cottage is located 1 mile from Southport, 2 minutes from the ferry's at Deep Point Marina & 20 minutes to the Oak Island beaches! While in Southport, enjoy the shops, the majestic Live Oaks, dine at fabulous cafes & restaurants with water views, take a carriage ride, watch the boats go by, go on a ghost walk or tour a museum. Southport has something for eveyone!

Location · Value · Sleep quality

Relax in a HGTV Beachfront pick!

Recently featured on HGTV's Beachfront Bargain Hunt, this picturesque cottage is located just steps from the beach and minutes to the boardwalk. With a large porch to hear the waves crash, one can enjoy a morning beverage with the sunrise and an evening cocktail at sunset. Impeccably maintained and stylishly updated, this cottage offers an easy way to relax. BBQ at home, play games in the spacious back yard, read books, walk along the white coast, or head out to the boardwalk for island fun!

Value · Family · Kitchen

Charming beach cottage blocks from the beach!

Recently remodeled!! Thanks for looking at my beach cottage! The house is only 4 blocks to the ocean and located right behind the lake where you will find a sidewalk around the lake for easy beach access. There is a farmers market around the lake every Saturday in the summer! This is a great house in an excellent location perfect for families and those that want to bring their fur babies. The backyard is large and fenced in. Fur babies are welcome with a one time $50 pet fee per dog

Location · Family · Wi-Fi

Charming Cottage, Walk to Beach, Porch, Parking

Charming Carolina Beach Cottage – Walk to Beach, Boardwalk & More! This upgraded 1900s cottage is in the heart of Carolina Beach—just 2 blocks from the ocean, boardwalk, restaurants, and shops. Central to all things CB, yet tucked on a quiet street. Unwind on the breezy front porch, then explore local favorites or take a short drive to Fort Fisher, the aquarium, or downtown Wilmington. We love this home and the easygoing CB vibe—and we hope you’ll feel like a local the moment you arrive.

Location · Value · Condition

Upscale beach cottage near beach

Wake up to salty sea breezes, sip your coffee on our deck and take a quick stroll to the beach! We are a top 1% guest favorite! Our beach home is fully equipped and family friendly or a couple's perfect beach getaway. The ocean is 3 min away via our street's beach access. Restaurants, shopping and fishing pier are all nearby. Neighboring Carolina Beach is a short ride away. Also, nearby to Ft Fisher State Park, the NC Aquarium and ferry terminal to Southport. Come relax at our place!

Value · Family · Beach

A-Frame | 3 Min Walk to beach | Boardwalk | Pets

This Beachy A-Frame is ready to host your next beach adventure! 3 bedroom : 2 bathroom and walkable to all Carolina Beach has to offer. - Located 1 block from the beach and short bike ride to the boardwalk. Next door to local restaurants, The Spot & Uncle Vinny's Pizzeria. - Whether staying a week or a couple of days, these peaceful island vibes will be something you want to return to. - Follow us @casasinthecarolinas , to see what is going on at The Sun Shack!

Location · Family · Laundry

Captain's Cottage | Historic | Walkable

Wake up to park views from rocking chair porches in one of Southport's most iconic homes — a beautiful coastal cottage on the first 100 lots. Steps from the waterfront, shops, and restaurants. The home boasts a commercial quality kitchen, unique touches throughout, and two cozy porches overlooking Historic Franklin Square Park. The location is ideal within walking distance of all that Southport has to offer and is a short drive to several beaches.

Value · Location · Check-in

Summer Lovin Kure Beach oceanfront with hot tub

Enjoy ocean views and direct beach access from this renovated Kure Beach cottage. Perfect for families or small groups! Highlights: • Hot tub with ocean view • Beach chairs, towels & umbrella • Full kitchen & dining • No shared walls • Smart TVs in all rooms • Pack & Play for families • 5-min to Ft. Fisher Aquarium • 15-min walk to Kure Beach Pier • 7-min drive to Carolina Beach • 25-min to Downtown Wilmington

Location · Value · Air conditioning

The Good Life

Enjoy this cozy cottage steps away from Carolina Beach! This 3 bedroom home has a newly renovated kitchen, can sleep up to 6, and also has a large fenced backyard so you can bring all your dogs with you. (Dogs only allowed) This home is located right on the 2nd row to the ocean, Carolina Beach Ave N, & is a convenient bike ride or short drive to restaurants, the Pier, Ferris Wheel, & our historic boardwalk!

Family · Location · Layout

Lucky Secret | Welcome Home to your Carolina Beach

Come enjoy newly renovated bungalow within two blocks of walking distance to the beach and the boardwalk to enjoy everything Carolina Beach offers. Enjoy a space where you can escape from the stressor's of every day life with an indoor outdoor experience. Enjoy a walk in shower and soaking tub after a day under the sun or cook a meal in the fully stocked kitchen. The world is yours here. We mean it.

Family · Location · Cleanliness