Cottage holiday rentals in Pleasure Island

Happy's Place Downtown Southport

This is my uncle Happy's place. It is in historic downtown Southport. Walking distance from restaurants, shopping, and the Cape Fear river. Located on a quaint alley just off the Main Street of town. This happy little cottage is nestled amongst large live oaks and in the shadow of Southport's iconic water tower. The home has one bedroom with a queen bed. The living area has a twin bed and two chairs. There is a full kitchen and small bathroom. Southport’s beautiful waterfront and parks await.

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!

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!

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!

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.

1913 Historic Downtown Empie-Possion Cottage

The Empie-Possion Cottage is located in the heart of historic downtown Wilmington, NC. The cottage is three blocks from the water and a 10 minute walk to the heart of downtown. The Empie-Possion cottage was built in 1913 and is expertly restored. Have a drink on the screened in patio in the back or on the historic front porch. Come enjoy a stay where you can truly unwind. This one of the most unique homes you can stay in Downtown and you feel it’s charm the minute you step in the door.

The Farmhouse at the White Barn Compound

Welcome to the latest addition to the White Barn compound! The original Farmhouse is now ready for guests and we're excited to share the bright spacious home with you. On the same property as the Carriage House and the Annex, everything you need for a relaxing stay is provided. Centrally located two miles from Wrightsville Beach, five miles from downtown Wilmington, and minutes to Airlie Gardens, Wrightsville Manor, and plenty of great restaurants and attractions!

Waterside Cottage 'HoriZen'

This is a recently renovated rustic 1947 cottage with an outstanding view of and access to the Intracoastal Waterway. It is perfect for meditation or quiet time by the water's edge, or for fishing, art, reading, writing, kayaking or paddleboarding. It is close to Wilmington, Wrightsville Beach, Topsail Island and Hampstead where there is shopping, restaurants, outdoor and cultural activities and beautiful beaches. It's old, but it is full of charm!

Oceanfront Incredible Ibis w private beach access

Sandy shorelines are calling you to this 3-bedroom, 1.5-bath vacation cottage on Oak Island! This beachfront property will leave you relaxed and rejuvenated. Panoramic ocean views from the deck! Our home offers a getaway that invites you to surf the waves, perfect your tan, and catch up on your favorite book while digging your toes in the sand. Featured in the Fall 2021 Hallmark film "One Summer." Enjoy a moment now!