Pet-friendly holiday rentals in Caswell Beach

Ocean View/Pup Lovin’/Steps to Beach/King Bed!

When ordinary vacations just won’t cut it, one destination will change everything you thought you knew about relaxation & hospitality. In a world of run-of-the mill rentals, comes an experience that defies expectations. Prepare yourself for a vacation that will make your Social media viewers question their life choices.  Critics are saying: “They have put so much thought into the details of this home” “Amazing experience!” Book now for a stay that will ruin all other vacations forever. 

Pets · Walkability · Location

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.

Pets · Walkability · Bathroom

Fox In The Sand - a favorite OKI beach home!

Fox In The Sand was renovated completely March 2022! Our home is located in the family friendly dog friendly coastal community of Oak Island, NC. LOCATED ON THE SOUTH SIDE OF OAK ISLAND Dr. NO MAJOR Road TO CROSS. Crossing the G.V. Barbee Bridge which is the closest to our home, a nostalgic feeling comes over you! This timeless town has attracted families year after year since the early 19th century. Our 10 miles of beach will always be our main attraction perfect for every outdoor activity

Outdoor spaces · Pets · Quiet

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!

Walkability · Outdoor spaces · Quiet

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.

Outdoor spaces · Pets · Location

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

Walkability · Pets · Comfort

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.

Pets · Walkability · Sleep quality

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!

Outdoor spaces · Pets · Quiet

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!

Walkability · Pets · Check-in

Oceanfront, pet friendly, fenced yard

Welcome to "The Boys of Summer Rental" ! Enjoy miles of unobstructed ocean views and a sandy beach right in your backyard. Relax on the huge covered porch with ocean breeze, watch dolphins, or boats pass by. The fully fenced yard is perfect for kids and pets. Just a 6-minute walk to restaurants, shops, and grocery. Plus, you have direct beach access for endless coastal fun!

Outdoor spaces · Walkability · Beach

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.

Outdoor spaces · Walkability · Indoor spaces

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.

Pets · Walkability · Nearby