Vacation rentals with a pool in Oak Island

Private Heated Pool, 4 mins to Beach, King Beds

Happy Hour at OKI by Hearth and Horizon Family Getaways – 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 neighborhood

2B/2B St James Coastal Marsh Condo w/ Porch & Pool

Welcome to Coastal Marsh Condo in St. James! 2B/2B - main w/King, Rainfall Showers, & Screened Porch on ground level with easy parking steps away. Our condo is a cozy mix of modern comforts & contemporary coastal charm. Southport (8 miles ~ 15 min) is a delightful coastal town where the river meets the sea and provides an abundance of fresh seafood, charming shops, alluring local artist galleries, & stunning water views. Oak Island (6 miles ~ 15 min) has an amazing wide beach for you to enjoy!

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.

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.

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!

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.

Scenic Getaway with Pool & Hot Tub

Add some peace and tranquility to your trip...beautifully furnished on the inside, fully stocked house, with an oasis of a backyard - this is a home you'll want to visit again and again. With your own HEATED saltwater pool & hot tub, in a private backyard paradise...you may not ever want to leave the property. Minutes away from the beach, steps away from the Intracoastal Waterway, and one street over from the scenic beach walkway, this house will not disappoint.

OIB Oceanfront 3 Bd, 2 Bth with linens!

Beautifully decorated beach themed OSW1 complex top floor keyless entry 3 bdrm, 2 bath oceanfront condo with panoramic views of the sea. This unit boosts a fully stocked kitchen, ready made beds with all linens and two baths with a set of towels per guest. New furniture, two large wall mounted TV’s, beach chairs, umbrella and beach towels are available for your convenience. Sat-Sat weekly rentals in season. No golf carts or trailers allowed. No pets allowed.

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.

The Villas at Oak Island #6, Pool & Ocean Views

This ocean view beach condo, part of The Villas at Oak Island, features 2 bedrooms, 1 full bathroom, and a fully equipped kitchen, along with a cozy combined living and dining area. Situated on the second row, it’s just a short walk to the beach, making it perfect for a family getaway. The Villas at Oak Island boasts a garden-style setting with an outdoor pool for your enjoyment. Linen, bath towels, and basic toiletries are provided for your convenience.

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

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.

Beach Cottage Getaway with a private pool!

Relax with the whole family at our beach cottage - enjoy a short 1/2 mile walk to the beach or the intercoastal or enjoy the private new inground pool with loads of decking, seating for the whole family and a screened in porch! Lots of room to spread out and great outdoor entertainment area with a fire pit. Large living room, dining room and kitchen and a workspace as well. Perfect spot to enjoy all that Oak Island has to offer!