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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.”
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Featured Homes
Total Package
New Listing! Amazing 7 bedroom Oceanfront Home!
5 (1)
BookSmart Properties presents: Total Package! Experience Coastal Elegance. This amazing home features 7 bedrooms and 6.5 bath. Enjoy the private pool or just a few steps further step out onto the beautiful Oak Island Beach. Discover the height of oceanfront living at Total Package, a stunning 7-bedroom, 6.5-bath vacation retreat on Oak Island, NC. Thoughtfully designed for both relaxation and entertainment, this new home offers the perfect backdrop for your next beachfront escape. Sorry, no pets allowed.
7 Bedrooms
8 Beds
6.5 Bathrooms
Lion by the Sea
Ocean Views! Pool, Spa, Private Backyard in OKI
5 (4)
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 miss out on this home!
4 Bedrooms
5 Beds
3.5 Bathrooms
Pop Pop's Plunder
Amazing OKI Home w/ Guest Apt, Pool, Grill Area
5 (1)
BookSmart Properties presents: Pop Pop's Plunder ! Welcome to your perfect vacation retreat — a spacious and versatile home designed for relaxation, comfort, and entertaining. This beautifully maintained property offers multiple living spaces, a private pool, and resort-style outdoor amenities, making it ideal for families, friend groups, or multi-generational getaways.
5 Bedrooms
7 Beds
3 Bathrooms
Oak Island, United States
Beachside Charm! Heated Pool, Spa & 3-Min Walk to Shore
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!
3 Bedrooms
5 Beds
2 Bathrooms
Oak Island, United States
Modern Family Retreat: Hot Tub & Fire Pit
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!
3 Bedrooms
5 Beds
2 Bathrooms
Oak Island, United States
Oak Island Oasis Steps to Beach, Local Cafes/Shops
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!
4 Bedrooms
6 Beds
3 Bathrooms
Oak Island, United States
Ocean View! Pool, Waterslide, Elevator & Firepit
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!
4 Bedrooms
6 Beds
3 Bathrooms
Oak Island, United States
NEW! Panoramic Ocean Views & Private Steps 2 Beach
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!
6 Bedrooms
11 Beds
3.5 Bathrooms
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.
Experience unforgettable vacation rentals managed with care, ensuring exceptional stays for every guest.
Have a vacation property?
Discover how we help owners earn more while doing less.