Holiday rentals with a pool in Southport

Sun-drenched beach condo with a view!

This beachfront property on Caswell Beach has one of the best views in the neighborhood. With three bedrooms, a spacious living room, renovated kitchen, and incredible light, it's truly the perfect vacation getaway - especially for groups of friends or family. Plus, there are two pools and the furniture is all new! The porch overlooks a nature preserve that not only acts as protection for our home against the elements but also as a home to many beautiful birds and deer you'll see during sunset.

2BR/2BA Condo in St. James–Near OKI/SPT & Beaches

Escape to a bright, recently renovated coastal condo inside the gated St. James. Perfectly positioned between historic Southport and Oak Island’s beaches. With two private bedroom suites, a king bed, a seasonal community pool, fast Wi-Fi, three Smart TVs and a fully equipped kitchen, the condo is ideal for families, couples or a relaxed coastal workcation. Spend the day at the beach, explore waterfront Southport, then return to a quiet and spacious retreat. Easy 13 mins drive to OKI beaches.

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.

Sleeps 18*1 Block to Beach*2 Master Suite*Gameroom

3-4 min. walk to the beach! 3 night min stay stay June-August 2026. Sleeps 18! Stay at our spacious "American Dreaming" cottage on Yaupon Beach/Oak Island and check off all of your vacation boxes! Sit by the firepit and listen to the sounds of the crashing waves, which are only 1 block away. Head down to the beach during the day and then cool off in our private stock tank pool while your kids play ping pong in the game room. Enjoy a short 10 minute drive down to historic Southport!

Private Heated Pool | 4 Min to Beach | King Beds

Happy Hour at OKI by Mountain to Waves – Just a 4-min verified walk to the beach! ✔ 4-minute walk to beach access ✔ Private heated pool ✔ Fully fenced backyard (perfect for pets) ✔ outdoor dining under a pergola, and a fire pit (wood provided). ✔ Arcade + air hockey for family fun ✔ Fully stocked kitchen for home-cooked meals ✔ Relax in 2 king bedrooms, including a spa-style primary bath with rain shower. ✔ Beach chairs, wagon & essentials included ✔ Quiet family neighborho

Escape to the Cape On the Gorgeous SPT Waterfront

Located on the beautiful Southport Waterfront you'll enjoy a well-appointed gem located within the RiverHotel of Southport that includes a small balcony with views of the Cape Fear River, guest pool, and private beach exclusively for our guests. We also have a huge deck with lots of tables and chairs to enjoy the spectacular water views! Covered parking is available within steps of the elevator. Make your Southport vacation memorable! Escape to the Cape awaits you!

The Coastal Coconut: Beautiful Ocean View Condo

This spectacular ocean view condo with top notch 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.

Sand Surf & Sunset Ocean View Condo - 2 Bed 2 Bath

Welcome to your perfect beachside retreat! This beautiful 2-Bedroom ocean-view condo in Caswell Beach, NC, offers breathtaking sunsets and panoramic ocean views right from your private covered decks - perfect for outdoor dining or unwinding to the sound of the waves. Just steps from the sand, this peaceful getaway is ideal for families or two couples looking to relax, recharge, and soak up the coastal charm. Walkable to restaurants, pier and golf.

Marina View Townhome

Enjoy a serene escape with a minimum 3-night stay at the Marina View Townhome, nestled at 314 Marina View Dr. in the charming town of Southport, NC. This meticulously furnished two-story haven offers picturesque vistas of the Southport marina and the tranquil Intracoastal Waterway. Immerse yourself in the local ambiance as you stroll or bike to nearby restaurants and shops, all conveniently located within a pleasant distance.

Brand New w/ Pickleball Court & Heated Pool

This brand new, modern retreat is perfect for families seeking the ultimate escape. Enjoy ocean views from the 3rd row balcony and an expansive backyard with a private pickleball court, basketball goal, and stunning putting green. Relax by the refreshing pool surrounded by a beautifully turfed yard. The ultimate personal oasis you'll never want to leave! You won't find another backyard like it in Oak Island!

No Cleaning Fee - Condo With Waterfront Pool/Beach

Visit the most adorable seaside village! Southport, with it's picturesque waterfront, fantastic restaurants, and adorable shops, has something for everyone. When you feel like staying closer to home, the pool will be calling your name for soaking in the sun while watching the ships sail by, and your private balcony is the perfect spot to sip a cup of coffee while watching the sunrise over the water.