Holiday rentals with a pool in Oak Island

Ocean Views! Pool, Spa, Private Backyard in OKI

BookSmart Properties presents: Lion by the Sea! This stunning home boasts ocean views, a private pool and spa (that can be heated for a fee w/ advance request), and an ideal location just blocks from OKI perks. Enjoy a private family cookout in the fenced yard, or dine together as a group in the spacious dining room after the chef of your family whips something up in the stocked kitchen! Each bedroom offers a private evening escape with coastal charm to add to the ambience. You don't want to mis

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.

OIB~Oceanfront Condo 3 BD/2BA, Linens Included!

3 bd, 2BA Oceanfront Condo in the sought after less crowded West End of Ocean Isle Beach! Only steps to the beach via our private walkway pass our complex pool. This tastefully decorated, freshly painted, keyless entry unit boosts amazing full panoramic views of the ocean, fully equipped kitchen with large island and comes with many new furnishings, all new Egyptian cotton bed and bath linens, new comforters, blankets and pillows. Sorry but pets, golf carts, RV’s and trailers are prohibited.

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 Black Pearl

Rooftop Deck, Ocean Views, & Backyard Oasis in OKI This modern OKI gem is only steps from the beach & boasts incredible amenities. Enjoy the best views from the rooftop deck, a unique and luxurious place to relax with a drink & the sounds of the sea. The contemporary interior offers stylish furnishings and decor, making the kitchen & living area as sleek as they are functional. You will sleep soundly in the comfortable bedrooms after a day at the beach or in the backyard pool. Book asap!

Oceanview House w/ Heated Pool — Walk to Pier

Indulge in the luxury of beachside living at Casa Allora, a stunning Oak Island Beach House. This exquisite newly built 5-bedroom, 3.5-bathroom retreat comfortably accommodates 11 guests. Revel in modern comforts with amenities like a private pool, BBQ grill, 3 king beds, 2 queen beds, 1 twin bunk and 2 oversized front porches. Whether you love watching the sunrise from the top porch or enjoy a glass of wine at sunset on the beach with the breeze in your hair, Casa Allora has it all!

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

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.

Luxury Family Retreat | Arcade | Pets Welcome

NEW POOL HEATER AND CHILLER! Step into your brand-new coastal getaway! This expansive 7-bedroom home with 10 beds and 6.5 bathrooms is ideal for large families and group stays. Enjoy quick beach access, a private pool with heater and chiller for all-season comfort, and an outdoor shower after sunny beach days. Inside, unwind with ping pong, foosball, and arcade games. Thoughtfully designed for babies, kids, and dogs—perfect for making lasting beachside memories.

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.