Holiday rentals in Fort Caswell

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Top-rated holiday rentals in Fort Caswell

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A spacious outdoor deck overlooks the ocean, featuring a large wooden dining table surrounded by several chairs. Lounge chairs are positioned for comfort, with vibrant sunset hues visible in the sky, creating a serene atmosphere.
Home in Oak Island
4.96 out of 5 average rating, 77 reviews

Oceanfront Dog Friendly*Caswell Beach* Views

Looking for a place to relax and bring fido? This is IT! This spacious Caswell Beach front home offers water views from the moment you step inside. If you prefer to spread out while lounging on the beach, Amazing GraySEA is the place for you. It's located past the Oak Island Lighthouse where beach access is only for the surrounding homes. The property is clean and well maintained. The owners provide lots of amenities, make every effort to ensure guests are comfortable and enjoy their stay.

Top guest favourite
The welcoming porch features a pair of rocking chairs and a swing, surrounded by greenery and potted plants. A colorful rug adds vibrancy to the entrance, while the house number is displayed on the front door. Natural light filters through, creating a peaceful ambiance.
Home in Southport
5 out of 5 average rating, 23 reviews

Heart of DT Southport+fenced yd - Maebel’s Cottage

Relax in my cute, sunlit cottage with a shady, private fenced yard in downtown Southport. Perfect for pets! Only 3 blocks from the water in a sweetheart location-right in center of bustling historic district but tucked away in a quiet nook. Sit in swing by street and feel ocean breezes with a peek-a-boo view of water at end of road. Fire pit - patio -2 miles from Fort Fisher and Bald Head ferries- 10 min from quiet, uncrowded Oak Island and Caswell beaches or just walk to shops and restaurants

Top guest favourite
A dining area features a long wooden table surrounded by chairs, illuminated by a chandelier. Decorative elements include a sideboard and a vintage mirror, complemented by a patterned area rug. Natural light enters through windows, enhancing the inviting space.
Cottage in Southport
4.96 out of 5 average rating, 361 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 favourite
A light blue golf cart is parked on a concrete driveway in front of a charming yellow cottage with a turquoise door. Lush greenery surrounds the entrance, and potted plants add a vibrant touch. The home features a covered porch that invites relaxation.
Home in Southport
4.99 out of 5 average rating, 128 reviews

Downtown Sunshine Cottage and Golf Cart

Charming, renovated cottage, just blocks from downtown. Ride the 6 seat golf cart to shops, waterfront swings, live music, riverfront dining, and spectacular sunsets. Only a 15 min car ride to Oak Island’s beaches & golf. Unwind in the gazebo, play bocce, or snuggle up for a movie by the fireplace. Sleep soundly in plush queen beds. Enjoy a clean kitchen with Keurig & lattes. Three smart TVs, 1.5 bathrooms and washer/dryer. Must be 24+ yrs old to book. (Signed waiver requested after booking).

Top guest favourite
The exterior of the single-story home features a well-maintained facade with blue and gray siding. A covered entrance leads to the front door, while landscaping includes neat shrubs and a green lawn. A one-car garage is visible on the left side.
Home in Southport
4.97 out of 5 average rating, 118 reviews

Southport Serenity

Welcome to this charming 3-bedroom, 2-bath home just 10 minutes from downtown Southport and Oak Island! Perfect for families or friends, this retreat features an open-concept living area, fully equipped kitchen, and cozy bedrooms. Enjoy the fenced-in backyard, ideal for pets or kids, and relaxing under the glow of string lights in the evenings. Close to beaches, dining, and shopping, it’s the perfect base for your coastal getaway. Book now and experience the charm of Southport and Oak Island!

Top guest favourite
A bright living area features a blue sofa and armchair, complemented by decorative pillows. A natural woven coffee table is placed on a soft blue and white area rug. Large glass doors open to a private balcony, allowing natural light and ocean views to fill the space.
Apartment in Oak Island
4.99 out of 5 average rating, 208 reviews

Rise and Shine! Beach, pool, & amazing views!

Welcome to RISE AND SHINE at Oak Island Beach Villas! Fabulous location on tranquil Caswell Beach. Close to amazing food, the iconic Oak Island Lighthouse, and top rated golf yet you feel the peaceful vibe of being on the east end of the island. Steps from the beach with breathtaking views, this beautifully decorated condo features 2 bedrooms, 1 bath and sleeps 5-6. Choose a short walk to the pool (seasonal) or simply relax on the private balcony listening to the soothing sounds of the ocean.

Top guest favourite
The front porch is adorned with colorful flowers in pots and features a small seating area. An American flag gently flutters above, while a gravel pathway leads to the entrance. Lush green trees provide shade, enhancing the inviting exterior of the cottage.
Cottage in Southport
4.97 out of 5 average rating, 463 reviews

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.

Top guest favourite
A serene balcony area is furnished with a comfortable seating arrangement featuring a light-colored cushion set. A small glass-top table sits on a patterned rug, surrounded by a white railing that provides an unobstructed view of the marina and moored boats.
Apartment in Southport
4.95 out of 5 average rating, 85 reviews

Romantic waterfront retreat

Tucked away at beautiful South Harbour Village Marina, this is the perfect place to unwind. Relax on the peaceful balcony overlooking the waterway, stroll to one of the nearby parks, or spend the day kayaking or boating with easy access to launches and transient boat slips. Located within walking distance to two restaurants (Italian & seafood), just minutes from the beach, and 15 minutes to picturesque downtown Southport, this is a perfect home base for exploring all the area has to offer.

Top guest favourite
The spacious living area features a cozy couch, a coffee table with games, and a television. Soft blue bedding covers the comfortable bed, and the room is lit by warm lamps and natural light from several windows adorned with blue curtains.
Guest suite in Southport
4.99 out of 5 average rating, 188 reviews

Southport Serenity, Entire full studio apartment

Entire studio apartment over the garage in a quiet family neighborhood. One mile from Southport's Historic and Picturesque Waterfront. Offers a full array of amenities from on-site parking, private entry, full bath, kitchen w/ refrigerator, microwave & single burner cooktop, blender, Keurig, dishes/utensils. Large living area with coffee table, chair, couch and desk. Games and books for your enjoyment. WIFI & Smart TV, outdoor shower, beach bikes and chairs. Patio area with Adirondacks.

Guest favourite
A welcoming living area features two comfortable sofas adorned with assorted cushions. A large fish wall decoration adds a nautical touch. A light-colored coffee table sits on a patterned rug, complemented by a small bar area in the background with a variety of beverages.
Flat in Southport
4.88 out of 5 average rating, 33 reviews

Waterfront Southport Retreat

Unwind at this peaceful, centrally-located Southport Retreat with an elevator. You'll love being right on the waterway with breath-taking daytime and sunset views! Here you are walking distance to all the best of Southport! Walk, bike, or drive to Fishy Fishy, the Provision Company, and many more waterfront restaurants you'll love! Walk, bike, or drive to all the quaint shops like Candy & Company Boutiques, the Southport Market, Southport Cheese Shoppe, and a must The Christmas House.

Top guest favourite
An aerial view captures the marina and waterfront of Bald Head Island, showcasing a series of white cottages nestled along the shore. Calm waters reflect the surrounding greenery, while the beach extends into the distance, framed by the gentle curve of the coastline.
Cottage in Bald Head Island
4.96 out of 5 average rating, 108 reviews

Air Cottage @ Bald Head Island

"Air" is a charming cottage located on the Bald Head Marina & the perfect home on BHI for a couples getaway, nomad traveler, or businessperson looking to enjoy the WFH lifestyle from a beach chair. Hi-speed Internet makes it easy to stay connected while taking in the views of the ocean and marina, or get out and enjoy nature. 5 min walk from Bald Head Island Ferry Terminal, restaurants, shops, rentals **Golf cart is included** **Shoals Club access available for additional fee**

Top guest favourite
A spacious bedroom features a large bed dressed in a light-colored patterned comforter with decorative pillows. Two bedside tables with lamps are positioned on either side of the bed. Natural light enters through a window adorned with light curtains, illuminating the wood flooring.
Apartment in Southport
4.97 out of 5 average rating, 156 reviews

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.

Popular amenities for Fort Caswell holiday rentals