Vacation rentals with a pool in Southport

A spacious outdoor seating area is shown on a wooden deck, featuring a table with several chairs. A stunning sunset can be seen in the distance, casting warm colors across the sky. Lush greenery is present in the foreground and background.

4.98 out of 5 average rating, 102 reviews

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.

4.97 out of 5 average rating, 156 reviews

A wooden walkway leads toward the beach, framed by lush greenery and a palm tree. The sun sets on the horizon, casting warm orange and yellow hues across the sky. Calm ocean waters reflect the evening light, creating a serene atmosphere.

Apartment in Kure Beach

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.

5.0 out of 5 average rating, 25 reviews

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.

Guest favorite

4.95 out of 5 average rating, 59 reviews

Spacious 2-Bedroom Condo in St. James Plantation

Sunny and serene private entrance third floor condo with 2 bedrooms and 2 baths at St. James Plantation. An easy drive to the quaint town of historic Southport and 12 minutes to Oak Island beaches. A screened in balcony to view the secluded tree-lined property and beautiful golf course. Enjoy fishing at the pier on the inter coastal waterway, walking and biking trails (map available in the condo for guests), as well as limited access to the St. James Beach Club on Oak Island (see notes below).

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.

4.99 out of 5 average rating, 218 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.

Guest favorite

A bright living room is furnished with a large blue sectional sofa, accented by a decorative pillow. Expansive windows frame views of the ocean and palm trees beyond. A ceiling fan circulates air while light spills into the space, creating a welcoming atmosphere.

4.97 out of 5 average rating, 97 reviews

Panoramic Ocean Views, 2 Pools, Huge Deck, Golf!

Your vacation awaits at this tranquil retreat on Caswell Beach, Oak Island! Embrace the serenity as you wake up to breathtaking ocean views and the gentle lull of waves. Recently renovated, this 3BR/2BA condo boasts an expansive deck, offering ample room for your family to relax and recharge. Just steps away lies a secluded beach with shallow waters, perfect for endless playtime with the kids. Take advantage of the nearby community pools and adjacent golf course for even more enjoyment.

A clear view of the Cape Fear River is presented, featuring a pool bordered by lounge chairs. A wooden deck extends towards the water, alongside private beach access and a dock. Bright blue skies and gentle clouds create a serene backdrop.

4.93 out of 5 average rating, 141 reviews

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!

A spacious living area features a comfortable sectional sofa facing a large window that offers ocean views. A ceiling fan adds to the airy atmosphere, while a wooden sideboard and round coffee table provide functional decor. Light enters from the sliding glass doors leading to the balcony.

4.99 out of 5 average rating, 233 reviews

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.

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.

4.98 out of 5 average rating, 170 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.

Guest favorite

Two blue wine glasses are positioned alongside a bottle of Clos du Bois wine on a table, with an expansive view of the ocean and shoreline in the background. The light reflects off the water, creating a serene atmosphere.

4.95 out of 5 average rating, 128 reviews

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.

4.98 out of 5 average rating, 115 reviews

No Cleaning Fee! New Condo w/ Waterfront Pool

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.