Vacation Home Rentals By Owner In Oak Island, NC

4 Bedrooms | 3 Full Bathroomsbr2 Kings | 1 Queen | 1 Double | 2 TwinsbrbrSearching for the ideal beach rental to serve as your homebase while you hop from adventure to adventure during your next getaway Then look no further than Lily’s Pad! Located on Caswell Beach, this ocean view home with a private pool and spa offers convenient public beach access and welcomes up to two dogs per stay.brbrStep into the cozy living room and settle on the curved sectional to watch a movie on the large smart TV or relax in front of the fireplace. Warm wood tones, shades of aqua and pops of tropical orange give off coastal vibes that harmonize with the gorgeous marsh views beyond. Pluck a novel from the mantle and settle in the recliner with your next beach read as you listen to shorebirds call.brbrThe wooden dining table is set for six but can seat up to eight for meals or a friendly game of UNO or Monopoly. Five additional seats are available at the adjacent breakfast bar. The kitchen provides everything you need to cook, whether you’re whipping up a quick afternoon snack or starting off the day with a full breakfast spread, along with plenty of serving and dinnerware. brbrEach bedroom in the home boasts a TV for personal entertainment, ceiling fans for comfort and the privacy of an en suite bath. The queen bedroom offers a pair of dressers and a wardrobe to ensure there’s plenty of room for your belongings. The attached bath is furnished with a pedestal sink and a step-in tile shower stall with a built-in shower bench. Thedownstairs king bedroom also provides a dresser for storage, and the shower stall for this bath features a wide door and walk in entry that make it easier to aid younger children. A laundry closet is conveniently located between these bedrooms with a full-sized washer and dryer.brbrThe rest of the bedrooms are located on the upper level with a door at the bottom of the stairs to offer extra privacy. The loft-style room with vaulted ceilings is divided into two bedrooms, one furnished with a king bed, and the other with a double, where you can wake up to views of the Atlantic via the sliding glass doors that lead to a small balcony. The full bathroom offers a vanity with his and hers sinks and a large step in shower stall with an antique-style rain showerhead. An additional sleeping nook on this level is furnished with two twin beds.brbrThe rest of the family has access to amazing outdoor spaces as well! Enjoy your coffee on the covered front porch as you watch the sunlight reflect on the waves or look for porpoises playing in the surf. Dine al fresco on the partially covered back deck as the kids play in the pool below, or just relax and enjoy the sweeping views of the horizon beyond.brbrThe pool area is fully fenced for safety and features both a pool and a spa, as well as classic pool loungers where you can relax and soak in the sun. Pool heating is available upon advance request with an additional fee. A park grill is provided for your family’s bar-b-que master, and you’ll also find a fish-cleaning station that your star angler can put to use. Tucked beneath the stairs is a sheltered outdoor shower with hot and cold water. While not fully enclosed, this convenient rinse off is still private and a welcome aid for washing sand off of babies and fur-babies alike.brbrWhen you’re ready to head to the beach, the closest access point is just four houses to the left and across the street. If you need a break from the sun and sand, a variety of adventures await, from exploring the Oak Island Lighthouse that’s practically next door to venturing over the bridge into Southport to explore the seaside town that you can see from your back deck! Or stay on the island and venture into the Oak Island city limits instead, where you’ll find a variety of shops, restaurants, arcades and other activities that you can reach in a short drive of five to ten minutes. We know that however you like to fill the hours of your beach vacation, Lily’s Pad is the jumping off point you’ve been waiting for!brbrGuests should note that an additional pool heating fee is required for each day a guest requests pool heating. Guest must request the pool heating and pay the fee by calling the OIA office during normal business hours at least 48 hours prior to arrival. Pool heating is only available when temperatures are 55 degrees Fahrenheit and warmer between October 1 and April 30 each year.

Lily's Pad: Coastal Cottage with Pool, Spa

Oak Island, North Carolina, United States

Bed

Bath

Sleeps

$471.12

4BR/2BA, BR1:1K, BR2:1Q, BR3:1Q, BR4:1Q - Vacationer's paradise becomes reality in this beautiful, spacious home with amazing marshland views. Beachy decor throughout, open living, dining and kitchen with a seating loft offering extended space for family gatherings. Large covered front porch on both first and second levels with ocean views and a large back sundeck and spacious back yard. HVAC, fully equipped kitchen with D/W, and refrigerator with ice maker, Microwave, cable TV's, ceiling fans, spacious bedrooms, laundry with W/D, enclosed outside shower. No Smoking, No Pets. Linens not included, please call or order online while booking your reservation. 3-night minimum rates available in Value Season. Please call our office to inquire. Check-In: 3-5PM, Check-Out: 10:00AM

As Good As It Gets / 3310 W Dolphin Drive

Oak Island, North Carolina, United States

4

Bed

Bath

8

Sleeps

$200.7

Nestled in the charming coastal town of Oak Island, this 3-bedroom vacation home invites you to experience the beauty of Long Beach. Gather your loved ones and step into a haven of comfort and convenience.brbrAs a traveler's favorite, this property boasts free WiFi, a washing machine and dryer, and a smart TV, ensuring you stay connected and refreshed throughout your stay. Venture out and explore the nearby Caswell Beach, just a 13-minute walk away, or drive 9 minutes to the iconic Ocean Crest Pier. For a day of leisure, head to the Southport Marina, just a 14-minute drive from your doorstep.brbrBack at the property, you'll find a fully stocked kitchen with a stove, oven, refrigerator, grill, microwave, dishwasher, and more, allowing you to whip up delectable meals. Enjoy your culinary creations at the dining table or step outside to the porch, where you can relax on the beach loungers and soak in the coastal ambiance. With 2 bathrooms, towels, basic soaps, an iron and board, and air conditioning, this home provides the essentials for a comfortable and carefree vacation.

3-bedroom vacation home just a 13-minute walk to Caswell Beach

Oak Island, North Carolina, United States

Bed

Bath

6

Sleeps

$246.41

Outdoor Shower | Dog Friendly w/ FeebrbrSun-kissed days and quiet evenings define this peaceful Oak Island vacation rental! After riding your bicycle to the beach or visiting top family attractions like the North Carolina Aquarium at Fort Fisher, walk your pup around the block while gazing at the Intracoastal Waterway. Getting hungry Grill up some burgers and dine al fresco in the spacious and fenced backyard. Don’t wait — secure your easygoing coastal escape today!brbr-- THE PROPERTY --brbrOUTDOOR LIVING br- Patio w/ gas grillbr- Outdoor showerbr- Fenced backyard w/ dining areabr- Front porch w/ bench swing & rocking chairbrbrINDOOR LIVING br- 3 Smart TVsbr- Dining tablebr- Queen air mattressbr- Washer/dryerbrbrKITCHEN br- Stove/oven, refrigerator, microwavebr- Drip coffee maker (starter coffee provided)br- Cooking basics, dishware/flatwarebrbrACCESSIBILITYbr- Single-story home, small step to enterbrbrPARKINGbr- Driveway (3 vehicles)brbr-- THE LOCATION --brbr- Close to Intracoastal Waterway & Scenic Walkwaybr- 1 mile to Ocean Crest Fishing Pier & Middleton Park w/ splash pad, playground & seasonal concertsbr- 2 miles to Oak Island Nature Center & various restaurantsbr- 5 miles to Caswell Beachbr- 7 miles to Oak Island Lighthousebr- 17 miles to North Carolina Aquarium at Fort Fisherbr- 32 miles to Downtown Wilmingtonbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $100 fee (+ fees & taxes, dogs only)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story home requires a small step to enterbrbrSECURITY CAMERA INFORMATIONbr- 2 exterior devicesbr- Location: tree, back doorbr- Coverage: front entrance, back entrance

< 1 Mi to Beach! Home w/ Fenced Yard in Oak Island

Oak Island, North Carolina, United States

Bed

Bath

7

Sleeps

$703.79

Welcome to your perfect beach getaway on Oak Island, NC! Nestled steps away from the pristine shoreline, this pet-friendly 4 bedroom, 4.5 bath vacation home offers a serene retreat for families and groups seeking relaxation and coastal adventures.brbrBuilt in 2023, it boasts a multitude of luxurious amenities, including an elevator, EV car charger, multiple balconies, a screened porch, an outdoor shower, 4 beach chairs to borrow, and so much more! It even has TWO master suites, and all 4 of the bedrooms feature en-suite bathrooms. Not to mention, you're within walking distance from the beach, Middleton Park, Kevin Bell Skatepark, Publix grocery store, and restaurants.brbrAs you step into the bright and airy living space, you're greeted by coastal-inspired decor and panoramic views of the surrounding natural beauty. Sink into the plush sectional sofa in the spacious living room, where vaulted ceilings and large windows invite in abundant sunlight and gentle ocean breezes. Kick back and unwind with your favorite book, or gather around the flat-screen TV for a movie night with loved ones. Behind you, there's a beautifully designed wet bar complete with a wine and beverage cooler to make accessing your favorite drinks easy!brbrThe fully equipped kitchen is stunning and beckons aspiring chefs to whip up delicious meals with modern appliances, ample counter space with a massive 9-foot-long island, and all the cookware you need. Enjoy leisurely breakfasts and snacks at the kitchen bar or gather for memorable family dinners at the dining table, which seats 8. For your convenience, you'll also find a half bath located on this top floor.brbrRetreat to one of the four inviting bedrooms for a private space to unwind, each with showers in the en-suite bathrooms and walk-in closets! The first master suite is located on the top floor and boasts a king-size bed, en-suite bathroom with soak-in tub, and direct access to the upper balcony with breathtaking ocean views. brbrHeading downstairs, you'll find the second master suite with its king-size bed, en-suite bathroom featuring a soak-in tub, and direct access to the lower balcony! Two additional bedrooms offer flexible sleeping arrangements and can be found down the hallway. They include a queen bedroom and a bunk bedroom with a twin over a king and pull-out trundle, ensuring a peaceful night's sleep for everyone. A dedicated laundry room completes this floor with a full-size washing machine and dryer.brbrReady to step outside onto the spacious deck, where you can savor your morning coffee as you listen to the soothing sounds of waves crashing on the shore Better yet, fire up the grill for a barbecue feast or dine al fresco at the outdoor dining table while the pups enjoy the fenced yard! On top of the outdoor shower and 4 beach chairs provided, additional amenities include high-speed wireless internet to stay connected during your stay, private parking, and yard games like corn hole and horseshoes.brbrWith its prime location just steps from the beach and near everything the island offers, this beach home offers the perfect blend of tranquility and convenience for your Oak Island vacation. Whether you're building sandcastles on the beach, exploring the island and nearby nature trails, or simply unwinding with loved ones, you'll create cherished memories that last a lifetime at this idyllic coastal retreat. Don't forget your four-legged friends — this home is dog-friendly, so your furry family members can join you for all the adventures. Book your stay today and start counting down the days to your unforgettable beach vacation on Oak Island, NC!brbrAbout Middleton ParkbrMiddleton Park is located right across the street from this home and offers a wide variety of activities for people of all ages. The younger travelers in your group will love the pirate ship-themed playground and cooling off at the splash pad water park in the warmer months! There are even numerous sports courts to take advantage of, including pickleball, tennis, and basketball courts. This complex is also home to dozens of local events throughout the year — from festivals and concerts to farmers' markets and sporting events. If you haven't guessed already, this is the place for outdoor recreation on the island and is only steps from Parkside Paradise's front door!brbrAdditional DetailsbrA pet fee is applied for those traveling with a pet and is included in your total rental rate. $175 for the first pet and $50 for an additional pet. Maximum number of pets allowed is 2. br brGuest reservations of 3 to 21 nights come with a valuable credit to use towards beach gear rentals during your stay! You may use your credit for bicycles, beach chairs and umbrellas, beach carts, kayaks, stand-up paddleboards, and more! The choice is yours! For this house you are eligible for up to $315.00 credit on any beach gear! Book now to reserve your gear today! ( Please note this is only available starting April 1, 2024 and October 31, 2024)brbrPlease Note: Linens are included with your reservation and contain the following: flat and fitted bed sheets, pillowcases, bath towels, hand towels, and washcloths.br brAs you will find when selecting dates on the calendar, there are minimum stay requirements based on the season. There is a 7 night minimum with a mandatory Saturday to Saturday rental pattern in the peak summer months, and there is more flexibility in the slower seasons. You can find a chart of our seasons and minimum stay requirements on our FAQ page, and please don't hesitate to reach out with questions!

4BR Luxury Home - Close to Beach Access & Dog Friendly!

Oak Island, North Carolina, United States

Bed

Bath

Sleeps

$1072.58

Discover the breathtaking beauty of Oak Island at Barefootin Bs, an exquisite oceanfront retreat perfect for your next family gathering or getaway with friends. This stunning 5-bedroom home comfortably accommodates up to 16 guests, offering a spacious and inviting atmosphere for everyone to relax and enjoy their time together.brbrAs you step inside, you'll be captivated by the refreshing coastal decor that complements the stunning ocean views. Each of the four elegantly appointed queen bedrooms invites tranquility with plush bedding, while the additional bunk bed room is perfect for the little ones, making it a great space for fun and laughter.brbrThe home features two full bathrooms, ensuring convenience and ample space for everyone. The open-concept living area invites you to unwind, with comfortable seating that encourages conversations and shared moments. The well-equipped kitchen boasts generous counter space and modern appliances, making meal preparation a breeze, whether you're whipping up a morning feast or indulging in a family dinner.brbrStep outside to experience the enchanting coastal breeze on the outdoor deck, where you can sip your morning coffee or enjoy evening cocktails while taking in stunning ocean views. The property's ideal location puts you just moments away from sandy shores and adventure-filled days at the beach.brbrWith nearby attractions like local dining, shopping, and breathtaking nature trails, there's no shortage of activities to explore during your stay. Whether you're lounging by the water, hunting for seashells, or enjoying water sports, your ideal vacation awaits.brbrBarefootin Bs promises comfort, style, and unforgettable memories, making it the perfect choice for your next escape to the coast. Book your stay today and start making cherished memories at this remarkable home!

Barefootin Bs, 5-bed, 2-bath—perfect for family fun!

Oak Island, North Carolina, United States

Bed

Bath

Sleeps

$263.44

Escape to the beauty of Oak Island with this 3-bed, 2-bath vacation rental near the Intracoastal Waterway! This home features a fully equipped kitchen, a washer and dryer, a privacy fence, and a screened porch. Head over to the Ocean Crest Fishing Pier and fish the day away or go kayaking on the nearby waterway. Whether you spend your days exploring the sandy beaches or indulging in fresh seafood, this cozy house is the perfect retreat for your next North Carolina getaway!brbr-- THE PROPERTY --brbr1,190 Sq Ft | Central A/C | Washer & Dryer | Walk to Intracoastal Waterway | 3 Mi to Pier | Privacy FencebrbrBedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: 2 Twin Beds | Additional Sleeping: Pack 'n PlaybrbrHOME FEATURES: Flat-screen TVs, en-suite bathroom w/ shower/tub combo, dining table, board games, laptop-friendly workspaces, outdoor showerbrOUTDOOR LIVING: Screened porch w/ lounge furniture, outdoor shower, deck, backyard w/ privacy fencebrKITCHEN: Stainless steel appliances, stove/oven, refrigerator w/ ice maker, dishwasher, drip coffee maker, toaster, dishware/flatware, knife set, cooking basicsbrGENERAL: Free WiFi, central heating, ceiling fans, complimentary toiletries, linens/towels, hair dryer, hangers, keyless entrybrFAQ: Stairs required to access, pet fee (paid pre-trip)brPARKING: Driveway (2 vehicles), free street parking (1 vehicle)brbr-- THE LOCATION --brbrSAND + SUN: Beach access (1 mile), Ocean Crest Fishing Pier (2 miles), Oak Island Pier (3 miles), Caswell Beach (5 miles), The Point (7 miles)brEXPLORE: Oak Island Nature Center (1 mile), Oak Island Lighthouse (6 miles), Fort Caswell (7 miles), North Carolina Maritime Museum at Southport (10 miles), Bald Head Island Ferry (11 miles)brTEE TIME: Oak Island Golf Club (4 miles), Founders Club (8 miles), Carolina National Golf Club (14 miles), Lakes Country Club (14 miles)brAIRPORTS: Wilmington International Airport (37 miles), Myrtle Beach International Airport (68 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking br- Pet friendly w/ $50 fee (+ fees & taxes, dogs only)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This property requires stairs to access

Dog-Friendly Oak Island Rental - 1 Mi to Beach!

Oak Island, North Carolina, United States

Bed

Bath

Sleeps

$396.71

Cheeky Tiki is a destination within your perfect beach vacation. This charming beach bungalow offers 3 bedrooms, 2 full baths, a wrap around porch, and a fenced backyard with a custom tiki bar for post-beach leisure and entertaining. Our home is a great getaway for family, friends, and your dog(s).brbrNestled in the heart of OKI, recently named North Carolina’s best-kept secret by Travel + Leisure, it is a 10-minute walk to the beach and a minutes drive to restaurants, bars and grocery stores.brbrThe spacebrThe Cheeky Tiki is nestled on 9th street, with beach access directly over the scenic intercoastal walkway.brbrOur Bungalow boasts 4 queen beds and 1 king bed across 3 rooms, including custom built in bunk beds the kids (and adults) will be sure to love. Our open concept living room, dining and kitchen allows for seamless entertaining and family time. Our kitchen is fully stocked with cookware, dishware and serving platters to make meals-in easy and convenient.brbrEnjoy coffee on our wraparound front porch, equipped with a gate for ease of mind with dogs and young children. A fully covered screened porch towards the back of the house leads you out to your fully fenced backyard.brbrEnjoy coffee on our wraparound front porch, equipped with a gate for ease of mind with dogs and young children. A fully covered screened porch towards the back of the house leads you out to your fully fenced backyard. brbrThe backyard boasts covered outdoor seating with a fire pit, a grill area, outdoor games including corn hole and a custom horse shoe pit, and a custom tiki bar––with a suspended TV, pool table, and fitness equipment. brbrKayaks, beach towels, and beach chairs are also available.brbrGuest accessbrGuests will have access to the entire home minus an owner’s closet.brbrOther things to notebrWe have left a manual with house rules inside, and to help make your stay extra special, we have curated notes from our experiences on OKI. Please read through it and let us know if you have any questions.brbrBe sure to stay up-to-date on the weather for your stay. We require all guests to leave our bungalow if the county declares an evacuation, such as for a hurricane. Also, please be aware of rip current conditions before swimming in the ocean. Our bungalow is located in a tropical environment.brbrPlease let us know if you have any questions about our house rules or environment. Accidents happen - if something breaks during your stay, let us know immediately.

Pet-friendly cottage with tiki bar 15-min walk from beach

Oak Island, North Carolina, United States

Bed

Bath

Sleeps

$249.73

NEW to PROACTIVE Vacations! Weaver's Inn-Let is the ultimate coastal getaway you've been dreaming of. This charming 2 bedroom, 2 bathroom property is perfectly situated just minutes away from both the pristine sandy beaches and the breathtaking Intercoastal Waterway. Imagine waking up to the soothing sounds of the ocean waves and spending your days soaking up the sun and enjoying the countless water activities available nearby.brbrLocated only 2 blocks from the beautiful Hannon A. Templeton park, you'll have endless opportunities for outdoor adventures and relaxation. For those who love fishing, the Ocean Crest Fishing Pier is just a quick 4-minute drive away, offering a fantastic spot to reel in the catch of the day. Whether you're looking for a fun-filled family vacation or a peaceful retreat to unwind and recharge, Weaver's Inn-Let is the perfect destination for your next coastal escape. Book now and start creating unforgettable memories in this idyllic seaside oasis. brbrThis is a NO PET property.

Weaver's Inn-Let 2 Bedroom 1.5 Bath Home in the Woodlands

Oak Island, North Carolina, United States

Bed

Bath

Sleeps

$433.53

**TWIN BUOYS**brSleeps 8. 3 bedroom/ 2 full bath Ocean View and Canal backed home. brbrCharming beach cottage that is steps from the beach with ocean views and canal views all around! Amazing sunsets and sunrises from the wrap around elevated deck. Relax in this 3 Bedroom, 2 full bath home that has been lovingly updated. No need to struggle looking for/pay for beach parking, just walk out the front door and you will be at the beach in less than a minute! Rinse off at the outdoor shower after the beach and then fish off the back yard or relax on the wrap around deck and enjoy canal and ocean views!! brbrSleeping accommodations are available for up to 8 people. The home's master bedroom has a queen bed with a full bathroom and ocean views. Bedroom #2 has a queen bed with ocean views, and Bedroom #3 has 2 sets bunk beds that sleep 4 and has canal views. brbrThe beachy furnished living room has a sectional sofa and chairs, a patio door the opens onto the deck and gorgeous canal views, a ceiling fan, flat screen tv, wireless internet, books, and board games. The kitchen features a full sized oven, dishwasher, fridge, pots, pans utensils, and dishes. The master bedroom has a washer and dryer for convenience. The garage has the beach necessities: Beach chairs, Beach wagons with wheels, a cooler, beach towels, kids games and toys. brbrShort walk to Middleton Park where you can enjoy free Summer Concerts, Splash Pads, Tennis, and more... Home is close to grocery stores, restaurants, bars, mini golf, and kids activities. brbrOnly dogs are welcome at the property. If you are bringing dogs, there is a pet fee and a maximum of 2 dogs allowed. No pets on the furniture. The pet fee does not cover damage done by pet or excessive cleaning needed if any. brbr**NOTE: You are responsible for any damage to the rental property and its accessories caused by you or anyone that's with your party. brbr**No motorized boats kept/parked on the property. brbr**IMPORTANT** There is no railing at the back and side canal. If you rent, you are releasing owner from any and all liability if someone/something falls in and gets injured/damaged in any way. brbrHOUSE RULES: brCheck in is 4pm or after, check out is before 10am. No events, No smoking and vaping inside and outside the home. Minimum age for primary renter is 25yrs. If you need certain dates and it won't let you book - message me - I will book less days if they are available. There will be an outside camera setup for the safety of cars, all outside amenities and of course, to discourage unwanted visitors. If you are going to be checking in late/after dark please let us know so we can turn the light on for you!br***For stays of 20 days or longer in the Off-Season, host will pay for up to $200/mo of utilities and guest pays remainder if any.

STEPS FROM THE BEACH! Waterfront home w/ocean & canal views. Fish off backyard!

Oak Island, North Carolina, United States

Bed

Bath

8

Sleeps

$1834.11

Welcome to Jolly Rogers Beach Paradise (previously Slow Your Roll)! Set along one of Oak Island's most coveted stretches of shoreline, this spacious oceanfront home delivers the kind of coastal escape that feels both effortless and unforgettable. With sweeping, unobstructed views of the Atlantic and direct beach access, the location alone makes it a standout—but the 7 bedroom / 5.5 bathroom home features and amenities take things to another level! Guests will enjoy a private elevated saltwater pool, multiple covered decks to kick back and relax, and a spacious floor plan perfect for large groups and families.brbrDesigned with classic coastal charm, Jolly Rogers Beach Paradise blends airy interiors with natural light and plenty of space to unwind after a day in the sun. The open concept living space, fully stocked kitchen, and expansive dining area feature large windows to take in the breathtaking views of the ocean. The perfect atmosphere for gathering, unwinding, and making memories together.brbrThe private elevated saltwater pool adds another layer of luxury, offering a refreshing retreat after a day on the sand or a peaceful place to lounge while listening to the waves nearby. Multiple decks and outdoor seating areas make it easy to enjoy morning coffee at sunrise or evening cocktails with panoramic ocean views.brbrWith generous square footage, an elevator, and 7 thoughtfully arranged sleeping areas, the home is ideal for multi-family trips. There's plenty of room for everyone to spread out, while still offering inviting shared spaces for meals, games, and quality time together. For added comfort, guests arrive with beds made prior to arrival. Whether you're planning a reunion, a group vacation, or simply a getaway with friends and family, Jolly Rogers strikes the perfect balance between space, comfort, and location.brbrIt's more than just a place to stay—it's a setting for lasting coastal memories.brbrBedroom Configuration:brEntry Floor (2nd Floor): Includes kitchenette, seating, and Smart TV. Pool Access is off of this floor.brBedroom 1 (Anchor Room): King Bed with shared bathroombrBedroom 2 (Whale Room): Twin over Full Bunk Bed with en suite bathroom shared with Anchor RoombrBedroom 3 (Starfish Room): Two sets of twin-over-twin-over-twin bunks (6 twin beds total)brBedroom 4 (Seahorse Room): King Bed with en suite bathroom that opens to hallwaybrBedroom 5 (Lighthouse Room): King Bed with ensuite bathroombrLiving Floor (3rd Floor): Kitchen, Dining Area, Living Area with Smart TV, and Bar Top Area. brBedroom 6 (Coral Room): King Bed with ensuite bathroombrBedroom 7 (Sand Dollar Room): King Bed with ensuite bathroombrbrAmenities:brPrivate Elevated Salt Water Pool with Sun Loungers Overlooking OceanbrLinens (Beds are made prior to arrival for your convenience)brElevatorbrGrill and utensilsbrWasher/DryerbrBeach Chairs and ToysbrShaboomi Shadebr70 Smart TV in Living RoombrFamily gamesbrCoffee Maker (Grounds and Pods)brBlenderbrRental Essentials Starter Supply (Paper Towels, Toilet Paper, Soaps, Coffee Pods, etc)brParking for 6-7 vehicles (depending on size)brCentral Heating and Air ConditioningbrCentral Whole-Home DehumidifierbrTankless Water HeaterbrSeating on all Deck AreasbrComplimentary Wi-FibrOutdoor ShowerbrPrivate Beach AccessbrbrUp to 2, behaved, potty-trained dogs allowed with payment of non-refundable pet fee.brbrThis property requires as minimum age of 25 to book.brAbsolutely NO SMOKING in the house or outside. This is a non-smoking property.brCheck in is at 4 PM and Check out is at 10 AM. We do not offer early check ins or late check outs from May - October.brbrThere are cameras on the outside of the property in the carport and on the back deck. These devices will be active 24/7 during your stay for security.

Jolly Rogers: Oceanfront Paradise with Pool, Sleeps 20, 7 bed/ 5.5 bath and two kitchens!

Oak Island, North Carolina, United States

Bed

Bath

Sleeps

$447.17

Key Amenities: brbr- 4 BR & 3.5 Bathrooms brbr- Dog Friendly brbr- Backyard Fire Pit with Chairs brbr- Large 70in Smart TV in Living Room brbr- Near Boat Launch on Intracoastal Waterway brbr- Parking for 6 cars Including a Boat and Trailer brbr- Screened In Porch brbr- Covered Porch brbr- Complimentary Welcome Bag with Starter Essentials brbr- Linens included for Free brbr- Beds made for you prior to your arrival brbr brbrWelcome to The Corner Yacht, your perfect Oak Island getaway! Nestled in a peaceful, wooded area just moments from the Beach and the Intracoastal Waterway, this spacious 4-bedroom, 3.5-bath home offers the ultimate mix of comfort, convenience, and coastal charm—and it's dog-friendly, so bring your furry friend along for the adventure! The Boat Launch for the intracoastal waterway is only 6 blocks away. There are 2 rooms with king beds, one with a queen bed and the 4th bedroom has a full bed along with twin bunks. The kitchen is well stocked with everything you will need to cook your favorite foods including a toaster oven, an air fryer and a Keurig coffee maker. brbr brbrWith plenty of parking, including room for a boat and trailer, this property is ideal for guests looking to explore the water. After a day on the beach or cruising the intracoastal waterway, unwind in one of several outdoor relaxation spots: gather around the backyard fire pit under the stars, kick back on the screened-in porch, relax in the shade of the covered porch, or catch some sun on the deck. A charcoal grill and outdoor shower add to the beachy vibe, and 4 beach chairs are provided for your trips to the beach. brbr brbrInside, the home is warm and welcoming with room for the whole crew. The living room features a 70” Smart TV, DVD player, basic cable, and free WiFi—perfect for movie nights or a quiet evening in. brbr brbrSleeping arrangements include: brbr brbr 2 bedrooms with king-size beds brbr brbr 1 bedroom with a queen-size bed brbr brbr 1 bedroom with a full-size bed and twin bunk beds—perfect for kids or extra guests brbr brbrDog-Friendly Amenities: brbrWe understand that your furry friend is part of the family, which is why our rental home is proudly dog-friendly. With plenty of space to roam and explore, as well as easy access to the beach for long walks and playtime, your four-legged companion will feel right at home during your stay. brbrPet Policy: brbrWe’re happy to host dogs! Depending on the booking platform, the pet fee may not be included in your total and will be requested separately. A non-refundable $200 pet fee (up to 2 dogs, 80 lbs combined) is required and must be paid before check-in—access details will be sent once completed. brbrMaximum of 2 dogs. Unregistered pets will incur a $200 pet fee plus a $500 remediation fee. brbrDogs must be up to date on vaccines and flea/tick prevention. No dogs on furniture or beds (additional cleaning fees may apply). Please bring a crate if needed; there is not one at the property. brbrStrictly no cats allowed. brbr brbrLocal Attractions: brbrBeyond the confines of our rental home, Oak Island beckons with a wealth of attractions and activities to suit every interest and preference. Spend your days lounging on the beach, swimming in the crystal-clear waters, or embarking on exciting adventures such as kayaking, paddleboarding, or fishing. Explore the charming shops and restaurants that line the streets of Oak Island, or take a short drive to nearby attractions such as the Oak Island Lighthouse, Southport Waterfront Park, or the North Carolina Maritime Museum. brbr brbrConclusion: brbrExperience the ultimate coastal getaway at our luxurious rental home in Oak Island. Whether you're seeking a relaxing retreat with loved ones, a fun-filled vacation with friends, or a memorable escape with your furry companion, our dog-friendly retreat offers the perfect blend of comfort, convenience, and style. Book your stay today and make memories that will last a lifetime at our seaside haven. brbr brbrPlease note: Linens are included with your reservation and your beds will be made prior to your arrival. Also a Welcome Bag will be waiting for you upon your arrival with starter supplies which includes 2 trash bags, paper towels, toilet paper, dishwasher powder, washing machine powder, dish sponge, small shampoo and conditioner with bar of soap, make up remover, and 2 bottles of water. brbr brbrHouse Rules: brbrCheck-in: After 4pm brbrCheckout: at 10am brbrNO SMOKING brbrNO PARTIES or EVENTS brbrPETS ALLOWED brbr brbrGuests must be 25 years or older to rent the property. Failure to follow this rule will result in tenant(s) removal from the property and forfeiture of rent money.

Dog-Friendly 4BR Retreat with a Fire Pit Located in the Serene Part of Oak Island –Near Boat Launch

Oak Island, North Carolina, United States

4

Bed

Bath

10

Sleeps

$253.52

John’s Crab Shack is proof that you don’t have to sacrifice comfort or location for affordability. This hidden gem delivers the perfect blend of charm, space, and convenience. Nestled on a wooded corner lot, this four-bedroom home is just a quick five-minute scenic walk (paved sidewalk) to the beach. Guests do not have to cross over the busy street of Oak Island Drive to get to the beach like similar homes in this price range. With two living rooms both equipped with TVs, separate dining room and fenced in backyard, John's Crab Shack's owners have lovingly decorated with your perfect family vacation in mind!brbrCreate lasting memories as you relax beneath the shady oaks in the private backyard, or load up the beach cart and stroll over the tidal creek to the recently renourished shoreline for sunbathing, swimming, or surf fishing. Rinse off in the private hot and cold outdoor shower, then unwind on the backyard deck with a good book and your favorite drink. Prepare a gourmet meal in the well-stocked kitchen or fire up the grill for an evening cookout.brbrFor rainy days, you’ll find plenty of games, puzzles, and books to keep everyone entertained. When you’re ready to explore, take a short drive to charming nearby Southport, filled with historic sites, shops, galleries, and fantastic restaurants. From Southport, take the passenger ferry to Bald Head Island, where cars are replaced by golf carts and you’ll discover pristine beaches, maritime forests, and the iconic Old Baldy Lighthouse. You can also take the vehicle and passenger ferry from Southport to Fort Fisher to explore its beaches, trails, aquarium, and historic Civil War site. Easy day trips to Wilmington and other popular coastal destinations are also within reach. Public floating and fishing docks are only a few streets from the home, and a convenience store is conveniently located just one block away on your walk to the beach.brbrWith plenty of room to spread out or get together for a family dinner, John's Crab Shack is truly a great family vacation home. The beautiful beaches of Oak Island are waiting for you—book your stay and start making memories. - Dog fee is $25 per night so please indicate if you are bringing a dog along with how many guest will accompany you.brbrMaster bedroom = 1 King + full bath, Bedroom 2 = 1 Queen & 1 bunk bed, Bedroom 3 = 1 queen, Bedroom 4 = full bed. Linens and bath towels included. Please plan to bring your own beach towels. brbrKeywords: Dog friendly family House with fenced in backyard, beach walk.

John's Crab Shack - Fenced Backyard - Close Beach Walk

Oak Island, North Carolina, United States

Bed

Bath

Sleeps

$932.94

5 Bedrooms | 3 Full Bathrooms | 1 Half Bathroombr1 King | 3 Queens | 2 Twins brbrPartially covered oceanfront deck with outdoor dining table and chairs, outside shower with hot and cold water. This property accepts 1 dog up to 60lbs each per reservation.brbrOpen concept living area with hardwood floors. The living room is decorated in a traditional style with dark leather furniture. The dining area can seat up to six with six additional seats at the kitchen island. The kitchen boasts dark wood cabinets, granite countertops, and stainless steel appliances. brbrBedrooms located on the south side of the home have incredible views of the Atlantic Ocean.brbrFive TV's (50-inch flat-screen TV with extended cable and DVD player in the living room), stereo, CD player and wireless internet.

A Villa Roja: Oceanfront Home with Incredible Views, Deck, Open Concept

Oak Island, North Carolina, United States

5

Bed

Bath

10

Sleeps

$669.3

Summary:brbrBookSmart 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.brbrbrbrThe Space:brbrBookSmart Properties is excited to welcome Pop Pop’s Plunder to our vacation rental collection! New to BookSmart but not to happy repeat guests, this Oak Island getaway offers the perfect blend of comfort, style, and versatility. Pop Pop’s Plunder is a spacious family-friendly retreat featuring a private pool, a guest suite, and a resort-style outdoor entertaining area which is ideal for families, friend groups, or multi-generational vacations. With multiple living spaces, modern amenities, and easy access to the beach, this beautifully maintained home is designed for relaxation, fun, and unforgettable memories.brbrbrbrMain Home:brbrThe primary residence features 3 bedrooms and 2 full bathrooms, with a comfortable layout perfect for families or couples traveling together. The open living space flows effortlessly into the kitchen and dining area, creating a warm, welcoming atmosphere.brbrbrbrGuest Apartment (Ground Floor):brbrIdeal for extended family or guests seeking privacy, the separate ground-floor apartment includes:brbr*A king bedbrbr*A daybed with trundlebrbr*A full kitchenbrbr*A private bathroombrbr*Please note: This apartment has a private exterior entrance and is not accessible from inside the main home.brbrbrbrPoolside Bedroom:brbrLocated just steps from the pool, the poolside queen bedroom offers a quiet retreat with its own exterior entrance — perfect for those wanting extra privacy during their stay.brbrbrbrOutdoor Oasis:brbrEnjoy the Oak Island sunshine in the large private pool or host unforgettable gatherings in the covered outdoor entertaining area, featuring:brbr*A spacious dining tablebrbr*Food prep area perfect for grilling and poolside mealsbrbr*Ample seating for lounging and relaxingbrbrbrbrThis amazing home is a short walk to the beach, past the park, at the 49th Street Beach Access. brbrbrbrWhether you're planning a family reunion, a getaway with friends, or a relaxing week in the sun, this home offers the space, comfort, and amenities to make your stay truly unforgettable.brbrbrbrGuest Access:brbrDetailed check in instructions and a unique access code will be provided prior to arrivalbrbrbrbr**Per HOA guidelines and local laws, the guests making the reservation must be at least 23 years old and be present during the entire duration of the stay. For non-family groups, all guests must be over the age of 23. If this rule or the home occupancy limit is breached, guests may be subject to fines or eviction.**brbrbrbrThe Neighborhood:brbrOak Island is a beach town that is separated from the mainland by the Intracoastal Waterway. Known primarily as a family beach town, it offers plenty of activities throughout the summer, including a variety of marathons/5Ks, live music, farmers markets, and more. The Intracoastal Waterway is popular for kayakers and fishing, and the town has plenty of golf courses, nature walks and biking for those who like to stay on land.brbrbrbrGetting Around:brbrThe exact property address and home details will be sent to you with the check in instructions so you can easily plan your travels.brbrbrbrOther Things to Note:brbrPayment schedule: 50% at time of booking, 50% or remaining balance due 30 days before arrival. brbrbrbrThe following violations may be subject to additional fines of up to $300: pets, late departure without approval by host & house left excessively messy. brbrbrbrHigh speed Wifi is an amenity that is provided at the property but we cannot guarantee functionality for issues that are beyond our control. Potential Wifi outages will always be handled in a timely manner and resolved to the best of our ability. Unfortunately it is not guaranteed that our solutions will fix the issue and refunds will not be given for Wifi malfunctions.brbrbrbrInteraction with Guests:brbrI am here for you during your stay, but our level of interaction is up to you. I'm only a phone ca;;/message away. You will be able to self check-in upon arrival.

Close to Beach, Pool, Grill Area, Bonus Apartment!

Oak Island, North Carolina, United States

Bed

Bath

Sleeps

$437.52

3 Bedrooms | 2 Full Bathroomsbr1 King | 2 QueensbrbrHidden among the beautiful trees on the island, Feelin' Tip Sea offers a sense of comfort with its contemporary style. With less than a two mile drive to the beach, you can take delight in relaxing by the water or watch the vessels sail by along the Intracoastal Waterway right down the street.brbrThe Living SpacebrbrThe open floor plan provides a place for family and friends to rest and unwind. The living room features a couch, a love seat and a recliner that surrounds the coffee table and the mounted TV on the wall. Additionally, the living room has an office desk and chair so you can work from home during your coastal retreat.brbrJust off the kitchen is a dining room table that seats six, which is great for gatherings with family and friends. Perfect for prepping coastal dishes, the kitchen's spacious black countertops are finished with a substantial sink accompanied by a modern island.brbrWhere You'll SleepbrbrThe serene master suite welcomes you. With the beautiful, bright walls and two windows for extra lighting, you're sure to get sunshine! The walk in closet is perfect to store away vacation essentials and feel right at home. The plush king-size bed makes for a great night's sleep. The private bathroom features a dual vanity and a large shower!brbrThe second bedroom is also furnished with a queen-size bed and equipped with a wall-mounted TV so you can enjoy your favorite shows or movie while de-stressing.brbrPast the shared full bathroom is the final bedroom, which has a queen-size bed and plenty of closet space.brbrOutside Living AreasbrbrWake up, meditate and enjoy your coffee on the spacious patio with outdoor seating! Enjoy being nestled away on the screen porch surrounded by beautiful trees.brbrThe front porch is an additional seating area to spend your day enjoying the island breeze!

Feelin' Tip Sea: Lovely Coastal Home with Fire Pit on Oak Island, NC

Oak Island, North Carolina, United States

Bed

Bath

Sleeps

$436.67

Discover The Chill Switch, a charming oasis nestled in the serene landscape of Oak Island, North Carolina. This delightful three-bedroom, two-bathroom home comfortably accommodates up to six guests, making it the perfect retreat for families or small groups looking to unwind near the coast.brbrStep inside to experience a warm and inviting ambiance, accentuated by woodland views that envelop you in nature's embrace. The spacious living area, bathed in natural light, features cozy seating where you can relax after a day of adventures.brbrWhip up delicious meals in the fully-equipped kitchen, complete with modern appliances and ample counter space, perfect for culinary creations that can be enjoyed at the dining table or al fresco in the outdoor sitting area.brbrFor relaxation, the bedrooms provide a peaceful haven, each thoughtfully designed to ensure maximum comfort. The two full bathrooms are well-appointed, stocked with essential amenities for your convenience.brbrStep outside to enjoy the tranquil surroundings. The outdoor space allows for lazy afternoons soaking up the sun or enjoying evening conversations under the stars.brbrWith its prime location, you're just a short trip away from Oak Island's beautiful beaches and local attractions, enhancing your vacation experience. Whether you seek adventure, relaxation, or a bit of both, The Chill Switch has everything you need for an unforgettable stay.brbrDon't miss out on this woodland retreat—book your getaway now and let The Chill Switch be your home away from home!

Experience a serene getaway at The Chill Switch in Oak Island, perfect for families!

Oak Island, North Carolina, United States

Bed

Bath

Sleeps

$520.53

Resting Beach Face (RBF) has been designed with the perfect island oasis getaway in mind. Come and relax by your large private heated pool with custom loungers, large and new back patio, and grill area. This modern 3-bedroom and 2 bathroom cozy home perfect for 1-2 families. Two of the three bedrooms are equipped with custom made king sized beds with brand new mattresses. The third bedroom has 2 queen sized custom made bed frames with a brand new mattress. This gorgeous redesigned home is perfect for two small families to come and spend a relaxing vacation. The spacious living room has been redesigned with a 65 inch flat screen television perfect for cuddling up and watching a movie after a long day at the beach. RBF has a kitchen that is open with both views of the living room and the pool. This is perfect set up to cook while safely keeping an eye on your children in the pool or in the living room. The kitchen has been redesigned to fit the needs of the ultimate cook. Down to the stainless steel appliances and endless cooking supplies, you will not need to bring anything from home. Resting Beach Face sits directly across the beach with ocean views from the front porch and public access a quick walk in both directions. RBF has beach chairs, beach wagons, sand toys, bikes, and enclosed child carriers that connect directly to the bike. RBF has everything that you need to have the perfect, private, relaxing vacation. All you need to bring are your clothes and your flip flops. This beautiful home is under new ownership and they have redesigned this beautiful home to meet the needs of their guests just as they expect when they go on vacation. This is truly the perfect getaway for a family or two families. RBF is a short walk away from the piers and a bike ride away from many of the local restaurants. If you want the perfect getaway without having to pack everything but the kitchen sink, then this is for you. Come and feel cozy, relax, and let us share our home with you. Our cleaning crew has taken and passed a course in COVID-19 disinfection. Take a vacation with a peace of mind that everything down to the soft luxurious linens has been safely prepped for you and your family. Resting Beach Face is waiting for you!

Private Heated Pool and Hot Tub, across the street from the ocean!

Oak Island, North Carolina, United States

Bed

Bath

Sleeps

$396.18

3 Bedrooms | 2 Full Bathrooms br4 Queens brbrDeck and screened porch with furniture, enclosed outdoor shower with hot and cold water and a charcoal grill.brbrWell-equipped kitchen with bar to seat three and a dining table that seats eight. Living room with a vaulted ceiling creates a large, open gathering space. brbrFour TV's (one Apple TV, three Roku devices for each bedroom), DVD player, Sonos Speaker system, CD player and wireless internet. Board games and puzzles.brbrThose with allergies should note that although pets are not allowed for guest stays, dogs may occasionally be present on owner reservations.

Apt Not: Comfortable, Open Home One Block from Beach with Screened Porch

Oak Island, North Carolina, United States

Bed