Pet-friendly holiday rentals in Caswell Beach

Whimsy Whale Cottage, Oceanview, Fenced Yard

We’d love for your happy beach memories to be made here at our cottage by the sea, The Whimsy Whale. Our island cottage is perfectly placed under a canopy of magnificent live oaks, about 300 steps away from the ocean. Nestled on a quiet beach access street, central to all the best attractions, shopping and eateries on Oak Island; close to attractions in Southport. It is one of our favorite places to spend time together and we look forward to sharing it with you, your loved ones and friends.

Oak Island Oceanfront 2BR Condo

Enjoy a perfect oceanfront family getaway on Oak Island's West Beach. This 1st level unit of our beach house has separate entrance, two bedrooms, one bathroom, and sleeps six guests. The kitchen is fully equipped with pots, pans, utensils, full size fridge, microwave, stove/oven, and dishwasher. Enjoy sunrises and sunsets on the huge deck watching the waves and the occasional dolphins. If your dates are not available, please check out our 2nd level unit availability at www.airbnb.com/h/oki2

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!

Pet Friendly/Game Room/Golf Cart - 3Bed 2Bath

Welcome to "5 More Minutes" beach house located near the ICW and Wooded section of Oak Island, NC. This open-floor plan home on pilings is on the island's west side and features a three-bedroom (three-bath)/two-full-bathroom configuration. Oak Island beaches are a short one-mile walk or drive away. We offer a 6-seater electric golf cart with a pre-paid parking pass to rent by the day. You must be over 21 to operate it. The golf cart rental fee is handled separately from the house rental.

"Just Enough" Beach Home! Screened Front Porch

"Just Enough" is just a short 3 blocks to the sand and the ocean for a great start to your relaxing dream vacation. Inner Coastal Waterway and Nature Center are on opposite end of 52nd Street. Relax on the enclosed screen front porch and listen to the ocean waves in the evening. The home has all new furniture, decor and bedding for you to enjoy. Kitchen is fully equipped and ready should you feel like cooking. "Just Enough" has everything you need to enjoy your time away from home.

Kid & Dog Friendly Stylish Ranch by Middleton Park

Welcome to Sweet Hideaways on Oak Island! This 3-bedroom, 2-bath home features an outdoor shower and a fully fenced yard. Enjoy beach essentials like chairs, umbrellas, boogie boards, and a gorilla cart for an easy trip to the shore. Family-friendly with a high chair, pack n play, toys, playhouses, and a fun custom mural! Just 0.7 miles to the beach and 1 block to the ICW. Walk to Middleton Park and the splash pad in minutes! Conveniently located near restaurants and shops.

Beach Cottage in the Trees, Dog Friendly

🐶 Welcome to our Beach Cottage in the Trees 🌳. A peaceful, dog-friendly haven for everyone in your family. This quaint, cozy “home away from home” is close to the beach (0.2 mi), local shopping, restaurants, and golf course, but in a quiet neighborhood away from the crowds. Beautiful screened-porch among the trees for relaxing, and a spacious back-yard on a wooded lot for all to enjoy. 📝PLEASE read entire listing and ALL rules prior to booking. 🐶DOGS always WELCOME.

Blue Turtle Beach Cottage

Welcome to the Blue Turtle Beach Cottage- we are a block from the beautiful Atlantic Ocean and offer the comfort and relaxing pace that personifies Oak Island. Wake up and enjoy coffee on your screened in porch overlooking the ocean, and walk up to the shops and restaurants that are only a block or two in the other direction. Quiet and private, yet convenient to everything- come enjoy all that wonderful Oak Island has to offer!

Oceanfront-pvt access-dog friendly-Incredible Ibis

Sandy shorelines are calling you to this 3-bedroom, 1.5-bath vacation cottage on Oak Island! This beachfront property will leave you relaxed and rejuvenated. Panoramic ocean views from the deck! Our home offers a getaway that invites you to surf the waves, perfect your tan, and catch up on your favorite book while digging your toes in the sand. Featured in the Fall 2021 Hallmark film "One Summer." Enjoy a moment now!

Cozy Cottage 10-15 min scenic walk from the beach!

~The Captain's Cottage~ Come unplug in this newly built cottage that is the perfect getaway. Two bedrooms, 2 full bathrooms, kitchen, a cozy living room, a fully fenced backyard and walking distance to the beach will provide you with the ultimate vacation. Pet friendly so your furry family members can join in the fun! Plenty of activities in the area, great restaurants, and fun for all ages!

Salty Porch | Water Views | Dogs | Near Beach

Welcome to Salty Porch, your relaxing Oak Island getaway! This dog-friendly 3-bedroom beach home sleeps up to 8 and offers beautiful Intracoastal Waterway views from the front porch rocking chairs. Just ½ mile from the beach and close to restaurants, coffee shops, and the pier, it’s the perfect spot for family vacations, fishing trips, or a peaceful coastal escape.

Oak Island Bungalow Steps to the Beach

Wake up and walk to the beach from this stylish Oak Island coastal retreat. Thoughtfully designed for relaxing getaways, this pet-friendly bungalow offers cozy luxury, outdoor lounging spaces, and everything you need for an easy beach vacation. Perfect for couples, families, girls’ trips, and long weekends by the coast.