Cottage vacation rentals in Pleasure Island

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Top-rated cottage rentals in Pleasure Island

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Top guest favorite

Cottage in Oak Island

4.99 out of 5 average rating, 188 reviews

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.

Top guest favorite

Cottage in Carolina Beach

4.99 out of 5 average rating, 153 reviews

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!

Guest favorite

Cottage in Southport

4.96 out of 5 average rating, 329 reviews

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!

Top guest favorite

Cottage in Carolina Beach

4.99 out of 5 average rating, 357 reviews

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. No cats.

Top guest favorite

Cottage in Carolina Beach

4.99 out of 5 average rating, 164 reviews

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!

Guest favorite

Cottage in Carolina Beach

4.96 out of 5 average rating, 178 reviews

One Beach’in Cottage, walk to the beach!

Remodeled 1940s Cottage! Walking distance to the beach and restaurants. The Cottage offers guests a relaxing front porch with a table, chairs and a porch swing. The cottage sleeps 4 guest comfortably with 2 bedrooms with queen beds. The Bonus room can sleep 2 guests. Please inquire if you need to sleep 5 or 6. Remodeled kitchen has new cabinets and appliances. We offer books, games, wifi and a roku to watch your favorite streaming apps. A tall privacy fence ensures the safety of your pets.

Superhost

Cottage in Carolina Beach

4.88 out of 5 average rating, 196 reviews

The Surf Chalet

3 blocks from the ocean and 1/2 block from the Carolina Beach Lake trail. Ample parking and private sun deck/shaded patio to wind down after the beach. Freshly renovated and decorated in March 22'. Perfect for families/couples looking to be close to the downtown action, yet away from any noise/traffic. A peaceful beach escape w/ every modern amenity. BBQ essentials on site. Pet friendly. Check out the Superhost's other similar Surf listings for alternative, curated offerings.

Top guest favorite

Cottage in Carolina Beach

4.92 out of 5 average rating, 125 reviews

Finding Dora - A Charming Vintage Beach Cottage

Enjoy the the beach life in this cozy vintage 1940s cottage in Carolina Beach. Located only one block from a beach access to the gorgeous white sand. Only steps from the Intercoastal waterway and a few blocks from restaurants, fishing charters, shops, and the boardwalk! This 2 bedroom/1.5 bathroom cottage has new furnishings, a stocked kitchen, portable crib, high chair, board games, beach towels and two smart TVs. Great for a romantic getaway or family vacation!

Top guest favorite

Cottage in Kure Beach

5 out of 5 average rating, 100 reviews

Upscale beach cottage near beach

Our Salty Casita beach home is fully equipped for a family or couple's perfect beach getaway. Proximity to the ocean (3 min walk) via our street's beach access. Restaurants, shopping and fishing pier are all nearby. Neighboring Carolina Beach is a short ride away to enjoy lively nighttime activities, shopping, boardwalk and restaurants. Also, nearby to Ft Fisher State Park, the NC Aquarium and ferry terminal to Southport. Come relax at our place!

Top guest favorite

Cottage in Southport

5 out of 5 average rating, 123 reviews

Captain's Cottage: The heart of downtown Southport

Step into history without sacrificing luxury at the Captain's Cottage! Located blocks from the water on one of the first 100 lots in Southport, is a beautifully furnished coastal cottage. The home boasts a commercial quality kitchen, spacious rooms 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.

Guest favorite

Cottage in Carolina Beach

4.9 out of 5 average rating, 241 reviews

100 yds to Beach | Back 2 School deals | Pets

Welcome to The Little Ray! NEWLY Renovated in 2025. 3 minute walk to the sand! 5 Minute walk to the boardwalk. - Private coastal, 1 Bedroom, 1 Bath, Full size kitchen. Downstairs beach cottage in Carolina Beach. Note : The upstairs unit is a separate unit. - 1 block from the beach and short bike ride to the boardwalk. Next door to local restaurants, The Spot & Uncle Vinny's Pizzeria. - Follow us on IG @casasinthecarolinas !

Superhost

Cottage in Kure Beach

4.84 out of 5 average rating, 106 reviews

Summer Lovin - Kure Beach oceanfront w/ 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