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Properties Under Management

5 star reviews

Average Response Time

“This place was exactly like the pictures. The house had everything to make you feel at home. Perfect location just a short walk to the beach. BookSmart always responded quickly to any questions we had. We even extended our stay and it was simple & easy.”

“My family and I absolutely loved our stay and BookSmart was a great host! The house worked for all of our needs and made for the perfect long weekend getaway.”
“Thank you so much BookSmart, you were an incredible host! You got back to me promptly and were so helpful! The beach is close by and utterly exquisite! Loved our stay!”
“We had an amazing stay! The house was perfect and BookSmart was an excellent host! I would highly recommend this home! It was clean, spacious and had all the amenities we could need.”
“The property was comfortable and felt like home instantly. The area was very peaceful from drinking our morning coffee on the screened in front porch to relaxing in the backyard by the pool or jacuzzi. Great location and very close to the beach which is an added plus. Looking forward to visit again.”

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Featured Homes

Oak Island/Ocean Isle
Outer Banks
Rock Hall, Maryland
Smith Mountain Lake
Oak Island
Ocean Isle

Address Oak Island, United States

Beachside Charm! Heated Pool, Spa & 3-Min Walk to Shore Rating 5 (1)

Mint 2 Be! Enjoy ocean breezes, a private heated pool, and a hot tub. The inviting front porch is ideal for watching sunrises and sunsets. Inside, find high ceilings, upscale lighting, and a chef’s kitchen with custom cabinetry and a gas range. The primary suite has a custom-tiled walk-in shower, plus two guest rooms, a stylish guest bath, and a walk-in laundry room. Close to Middleton Park’s attractions. Your perfect island getaway awaits!

Bedrooms 3 Bedrooms Beds 5 Beds Bathrooms 2 Bathrooms
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Address Oak Island, United States

Modern Family Retreat: Hot Tub & Fire Pit Rating 5 (16)

Cub's Cottage! This beautiful Oak Island home is only half a mile from the beach & is perfect for your family's vacation! The interior is fully updated, offering a shining & modern kitchen, a welcoming living room, & airy bedrooms tailored for coastal comfort. Don't miss out on a perfect evening in the newly renovated fenced backyard, which stars a fire pit, hot tub, corn hole boards, and palm trees. Plan your stay in Oak Island with your family at Cub's Cottage!

Bedrooms 3 Bedrooms Beds 5 Beds Bathrooms 2 Bathrooms
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Address Oak Island, United States

Oak Island Oasis Steps to Beach, Local Cafes/Shops Rating 5 (18)

Puffin Run! Located a short 2 min walk from the beach and featuring a gorgeous interior, your family of 11 will love the amenities this home has to offer. With a cozy firepit, enclosed sun room, bedrooms w/ lovely coastal decor, a sparkling modern kitchen/dining area, and an inviting living room, you don't want to miss out on this home. Perfect location near the beach, parks, local shops and restaurants, Puffin Run will book fast, so plan your vacation today!

Bedrooms 4 Bedrooms Beds 6 Beds Bathrooms 3 Bathrooms
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Address Oak Island, United States

Ocean View! Pool, Waterslide, Elevator & Firepit Rating 5 (25)

Sea La Vie! This stunning Oak Island home is perched perfectly to offer breathtaking ocean views as far as the eye can see. Fall asleep in one of the 4 cozy bedrooms, or enjoy the views from the decks & living room! The kitchen is beautifully updated and fully stocked for the chefs in your group. A gorgeous pool area awaits outside, with a water slide, lounge chairs, outdoor dining, and a fire pit. Book your stay today, and begin your life at the sea!

Bedrooms 4 Bedrooms Beds 6 Beds Bathrooms 3 Bathrooms
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Address Oak Island, United States

NEW! Panoramic Ocean Views & Private Steps 2 Beach Rating 5 (2)

New Listing with Renovated Interior! Step onto the beach (literally) at this gorgeous Oak Island home. Private beach access directly from the deck makes beach days a breeze, while the beautifully appointed interior provides every comfort. The kitchen is large and stocked for the chef of the family, and the living room sets the coastal vibe. 6 bedrooms provide plenty of sleeping options for everyone, and 3.5 baths offer convenience. Don't pass Bahama Tease up, come and stay in Oak Island!

Bedrooms 6 Bedrooms Beds 11 Beds Bathrooms 3.5 Bathrooms
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Experience the BookSmart difference.

Quality Assurance:

Industry leading cleaning standards

In-depth home inspections

Luxury amenities

Customer Support

100% response rate

<15 minute average response time

Customer support call/text line

Booking Confidence:

Secure payments

Price transparency

Booking protection

Local Experience

Custom welcome guides

Recommendations on local dining and activities

Local partnerships

Frequently Asked Questions.

Your Questions Answered

Where can I find the best deal for my vacation?
You’re in the right place! Booking directly though our BookSmart website will save you from those pesky platform fees.
Do you offer travel insurance?
Yes! When you go to reserve a home, during the check out process you’ll have the opportunity to purchase travel insurance.
How do I access the property after I make my reservation?
Once the reservation is confirmed, you will be emailed a confirmation and a link to our detailed welcome guide. Prior to your arrival, detailed check in instructions along with an electronic door code will be sent.
After I book, how do I pay?
50% of the reservation will be collected at the time of booking and the other half will be collected 30 days prior to your arrival.
If I need assistance during my stay, how do I get in contact with BookSmart?
Once the reservation is made, we’ll provide you with our dedicated email and support line (call/text) available if you have any questions or need assistance!
What supplies are included in my stay and what do I need to bring?
At no additional cost to you, all beds are made with fresh linens and each guest will receive their own towel set. All of our homes come equipped with starter supplies, including the essentials – conditioners, soaps, shampoos, paper products, etc.. Check your welcome guide for more specific information related to your property.

Better homes, better stays when you BookSmart.

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