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.

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

Southport Serenity

Welcome to this charming 3-bedroom, 2-bath home just 10 minutes from downtown Southport and Oak Island! Perfect for families or friends, this retreat features an open-concept living area, fully equipped kitchen, and cozy bedrooms. Enjoy the fenced-in backyard, ideal for pets or kids, and relaxing under the glow of string lights in the evenings. Close to beaches, dining, and shopping, it’s the perfect base for your coastal getaway. Book now and experience the charm of Southport and Oak Island!

Its a "Sweet Little Cottage On Oak Island"

Oak Island; a serene south facing beach you will love to stroll. "Sweet Little Cottage" is so close -1 1/3 short blocks away with no major street to cross. Stroll or bike the tree lined streets.Feel cool ocean breezes, hear soothing ocean sounds.Within walking distance to library, shopping, eateries, oceanfront dining coffee shop, ice cream parlor, Yaupon Pier Short drive to Community Center Exercise/Weight Room, tennis, basketball,Oak Island Golf Course. Small and medium dogs allowed.

turtle time - Hot Tub, Walk to the beach

Escape to turtle time, a cozy retreat, 5-minute walk from public beach access at the end of the street, with no busy roads to cross. You’ll be half a mile from the Oak Island Pier and within walking distance of local restaurants and shops. After a day in the sun, unwind in the private hot tub. This charming one-bedroom, one-bath apartment is ideal for couples seeking a peaceful coastal getaway. Well-behaved dogs are welcome with prior approval at booking and an additional pet fee.

Pelican's Perch, Oak Island, NC

Welcome to our Guesthouse...2-Minute Walk to Ocean / Direct Beach Access. Cozy house with charming furnishings. Full service kitchen with refrigerator, microwave, stove, K-Cup coffee maker and toaster, queen bed and comfy furniture in the living room. Bath w tub/shower. Flat screen TV - YouTube TV/WiFi included. Outside shower for your use while you are visiting with us. Private deck to grill your food. Close to shopping and restaurants. 2 person maximum. 2 dog maximum.

Pawtucket - dog friendly, short walk to beach

Dog friendly, recently renovated 2 bedroom home (~900 sq ft) - on Oak Island. ~ 0.3 mile to beach. Within walking distance to Publix, donut shop, Middleton Park , tennis courts and eateries. Includes large fenced in yard for fun with family and pet(s) along with outdoor shower. TVs (WiFi w/you tube tv) in living room and both bedrooms . No smoking on premises. Come enjoy the dog days of summer (or any season)! (House is on pilings so must be able to climb stairs)

You, Me and the Sea - kid and dog friendly, linens

Book your perfect beach vacation at our beautiful 3 bedroom home with easy access to both the beach and intracostal. Only 1/2 mile from the beach (easy 10 min walk) or easy drive to beach access on 55th street. Close proximity to everything you need... grocery, restaurants, newly renovated Middleton Park with playground, splash park, basketball and pickle ball courts. Located a short drive to the quaint town of Southport.

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!

Dog Friendly, quick walk to the beach w/ linens!

“Turtle’s Trott” is just a block and a half from the beach and is ready to host your next coastal getaway. With its open-concept layout and inviting atmosphere, this home is perfect for families or friends to gather—whether it’s for game nights, shared meals, or movie marathons. This dog-friendly home welcomes up to 2 dogs with a $200 pet fee. Conveniently located near great restaurants, local shops, and a bakery.

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!

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!