Holiday rentals with outdoor seating in Bald Head 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.

The Surf Lodge

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 Lodge listings for alternative, curated offerings.

Surfrider Siesta -Indoor Pool -Hot Tub - Elevator

Relax with the family at this peaceful retreat. Surfrider Siesta is a very comfortable, family friendly place to stay. Fully equipped with all the cooking essentials, washer & dryer unit within condo, WiFi and cable. Private beach access is 100 steps from the front door. The complex has three outdoor pools which are seasonal and a recreational building with a heated indoor pool open all year round. It also has sauna, hot tub, gym and changing rooms. Sorry no pets allowed in rentals as per HOA.

Southport Tree Escape * King Studio Near Downtown

“Perfect for two. Easy access. Very quiet.” – William, ‘25 This vaulted studio in the trees is the perfect setting for a romantic getaway or a weekend respite – and it’s just a short walk from the heart of Southport, America's Happiest Seaside Town. You'll be hosted by year-round Southporters who have taken great pride in creating a space that's comfortable and contemporary – but with all the charm and small-town feel - close to dining and the waterfront but in a special private location.

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 town's main street, this happy little cottage is nestled among 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.

Oceanfront Duplex~ linens included!

2 bdrm, 2 1/2 bth oceanfront duplex with 3 pools and tennis courts! Bed and Bath linens included! Private driveway for Golf cart rental permitted. Sorry, strict no pet policy. Sat -Sat weekly rentals in summer season. PLEASE NOTE: All three pools are for our guests to use and are maintained thru the HOA and we do not have any control over exactly when they open (Usually April 1st ) or if any of them closes for any reason. No refunds will be given if any of the pools are closed temporarily.

Cozy BHI Condo - Community Pool and BHI Club

Welcome to "Marooned Five". We enjoy sharing our home so others can experience the beauty and magic of Bald Head Island. Our home has 2 bedrooms, 2 full baths, fully stocked kitchen (renovated March 2024 and 2022!) & a spacious loft for the kids. Located in Royal James Landing, a private pool and picnic area are available for use just a few steps away. There are 6 bikes (4 adult/ 2 child) & 2 4-person golf carts. Guest memberships for the BHI Club are available for an additional fee.

Sandpiper~ Beachfront Cottage (pet-friendly)

Original beachfront cottage on Holden Beach, just steps from the sand and water. Enjoy the dolphins and shorebirds from the rockers on the covered porch. Cozy studio has been renovated with thoughtful upgrades. Kitchen is fully stocked including coffee maker, spices, condiments, and premium cookware. No stairs, ground-level are ideal for children, older guests, and pets (pet fee collected separately). Lots of amenities and beach items are provided for your comfort and convenience.

Southport’s Southern Charm

Quaint coastal condo located close to all Southport has to offer. This 1 bedroom 1 bath condo right on the main street of Southport! You’ll have a restaurants, shops, and bars within easy walking distance! The large balcony, with covered and uncovered areas has large palm trees and a good view of Howe St. You’re only 6 blocks from the water! The condo comes with everything you could ever need. Wine, snacks, and coffee come standard. Come see why Southport is our “Safe Haven”!

The Coastal Coconut: Beautiful Ocean View Condo

This spectacular ocean view condo with top notch 2022 renovations is just steps from the beach. Be swept away by the view of the rolling waves, whitecaps, and the OKI Pier as you relax and enjoy a beverage on the balcony. You will also be treated to a breathtaking sunset as the colors change each minute across the sky. Retire to the living room and rest your tired feet on a comfy sectional sofa as you interact with others in an aesthetically pleasing open floorplan setting.

Stones Throw to downtown Southport

Welcome to our gorgeous 1 bedroom/ 1bath home away from home! These roomy accommodations are just steps from the Southport Marina and in the heart of historic Southport. You have at your disposal boat parking, outdoor pool area, and walking access to Southport's many charms, such as fine dining and shopping. Bikes and beach chairs are in the closet in the covered parking. Your relaxation begins with easy self check-in and keyless entry! Enjoy your stay.

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.