
Holiday rentals in Oak Island
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Top-rated holiday rentals in Oak Island
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Quiet, chic coastal retreat: the Secret Sandshake
It’s all here! Escape and unwind at our calm, quiet, newly renovated (from the ground up) 1965 cottage on the residential end of family-friendly Oak Island. ✓ 10 minute walk to the beach ✓ Thoughtfully designed and renovated, comfortably appointed, meticulously maintained, stylishly decorated ✓ Fully-equipped dream kitchen with electric range/oven, dishwasher, and all the essentials ✓ Large screened porch with swing and ceiling fan ✓ Super-sized lot with native trees on a peaceful cul de sac

Rise and Shine! Beach, pool, & amazing views!
Welcome to RISE AND SHINE at Oak Island Beach Villas! Fabulous location on tranquil Caswell Beach. Close to amazing food, the iconic Oak Island Lighthouse, and top rated golf yet you feel the peaceful vibe of being on the east end of the island. Steps from the beach with breathtaking views, this beautifully decorated condo features 2 bedrooms, 1 bath and sleeps 5-6. Choose a short walk to the pool (seasonal) or simply relax on the private balcony listening to the soothing sounds of the ocean.

Prime OKI location; walk to 43rd St beach access
Welcome to our Coastal Oasis! Our space is 3 bedrooms (4 beds+ pack and play+ bassinet), 2 bathrooms, outdoor shower, extra large screened in front porch and back deck with dining area and grill. Our home caters perfectly to families (including those with infants and children) and everyone in between! Between lounging on the front porch (rocking chairs, egg chair, and couch set) or listening to music while grilling out back, we hope your time here is nothing but happy memories and fun times!

Oak Island Oceanfront 2BR Condo
Enjoy a perfect oceanfront family getaway on Oak Island's West Beach. This 1st level unit of our beach house has separate entrance, two bedrooms, one bathroom, and sleeps six guests. The kitchen is fully equipped with pots, pans, utensils, full size fridge, microwave, stove/oven, and dishwasher. Enjoy sunrises and sunsets on the huge deck watching the waves and the occasional dolphins. If your dates are not available, please check out our 2nd level unit availability at www.airbnb.com/h/oki2

Linens Included/Dog Friendly "Oak Island Oasis"
Enjoy a relaxing stay at a spacious 3 bed/2 bath kid and pet-friendly beach cottage in beautiful Oak Island. Oak Island Oasis is a newly renovated house that is tastefully decorated and fully stocked with all your beach vacation needs. Enjoy a sunset on our uncrowded beaches, fish, boat or enjoy a nature walk along the Intracoastal Waterway and the Davis Canal. There is shopping, dining, and all the amenities you'd expect in a quaint beach town just miles away from your coastal get-away.

Sea Trees House
Let’s get your summer getaway booked! This well-maintained home offers cozy gathering spaces for coffee or grilling on the screened porch, outside dining, or gathering at the fire pit. Relax on the front porch swing and enjoy the shelter of mature palmettos and live oaks surrounding the house. A quiet street and a seven minute walk to the beach make this house a great refuge after a day of fun in the sun with a cool, shady spot to relax with family and friends. The days are booking fast!

Charming 60s Bungalow 3 Min Walk Beach Wine Shop
Includes: 2 bikes, beach wagon, chairs, umbrellas, towels, and blankets. Have fun with the whole family at this stylish, charming mid-century cottage! Drop your bags and head to the beach! This unique mid-century charmer is perfectly situated on a quiet street with ocean access at one end and the Intracoastal Waterway at the other. This cottage offers the best Oak Island living, just a 3-minute walk to the beach, local restaurants, shops, and more. Shibumi rental option via QR code..

Kid & Dog Friendly Stylish Ranch by Middleton Park
Welcome to Sweet Hideaways on Oak Island! This 3-bedroom, 2-bath home features an outdoor shower and a fully fenced yard. Enjoy beach essentials like chairs, umbrellas, boogie boards, and a gorilla cart for an easy trip to the shore. Family-friendly with a high chair, pack n play, toys, playhouses, and a fun custom mural! Just 0.7 miles to the beach and 1 block to the ICW. Walk to Middleton Park and the splash pad in minutes! Conveniently located near restaurants and shops.

Classic Coastal Beachside Cottage
Completely renovated Shell Cottage on sleepy Oak Island is an easy 5-minute stroll to the ocean and Middleton Park. Publix and restaurants within walking distance. Ideal for couples, solo travelers and small families 1 level cottage (No Stairs!). Enjoy slow, relaxing beach days and cozy evenings in this thoughtfully curated cottage. The perfect setting to create lasting memories with family and friends! Easy access to Southport antiquing and exploring Bald Head Island.

The Coastal Coconut: Beautiful Ocean View Condo
This spectacular ocean view condo with top notch renovations is just steps from the beach. Be swept away by the view of the rolling waves, whitecaps, and the OKI Pier as you relax and enjoy a beverage on the balcony. You will also be treated to a breathtaking sunset as the colors change each minute across the sky. Retire to the living room and rest your tired feet on a comfy sectional sofa as you interact with others in an aesthetically pleasing open floorplan setting.

Great Marsh View & 2 Blocks to Beach-LongStayDscnt
Escape to Oak Island's tranquil shores and the serenity of the marsh at The Hammock House. This 2-bed, 2-bath haven is surrounded by picturesque marshlands with breathtaking views and the ocean waves just 2 blocks away. Grill out and dine al fresco, relax in the hammocks or lounge in the super comfy living room after a long day at the beach. Enjoy the peace and quiet of the Carolina beaches. LONG STAY DISCOUNT Dec-March $2,500 plus taxes and fees. Send us an injury.

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)
Popular amenities for Oak Island holiday rentals
Other great holiday rentals in Oak Island

Charming Beachfront Cottage/Direct Access to Beach

Terrapin Station Beach Cottage- Beach Front

1960's Ocean Front Cottage

NEW! 0.5 miles to the beach!

New, Oceanfront, 50 Steps to the Sand, Pool, Views

Pool | Views | Sleeps 8 | Linens | Yacht Drive

Sunny Boy - Great Location in the Heart of OKI

Wonderful New Dog Friendly Home, 6 Seater GolfCar
When is the best time to visit Oak Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $204 SGD | $204 SGD | $220 SGD | $238 SGD | $271 SGD | $337 SGD | $347 SGD | $315 SGD | $260 SGD | $233 SGD | $230 SGD | $235 SGD |
| Avg. temp | 8°C | 10°C | 13°C | 18°C | 22°C | 26°C | 28°C | 27°C | 24°C | 19°C | 13°C | 10°C |
Frequently Asked Questions
What are the best places to stay in Oak Island?
Oak Island has neighborhoods near the shoreline with convenient access to local cafes and shops. Many guests explore accommodations along the beachfront or in quieter residential areas, with family-friendly options available throughout the island.
What are the best things to do in Oak Island with kids?
Families often explore sandy beaches, visit playgrounds near the shore, and participate in seasonal crabbing or fishing. Simple mini-golf courses and nature walks make for engaging kid-friendly activities around town.
What are some of the best things to do in Oak Island?
Oak Island has broad beaches for sunbathing, fishing piers, and kayak-friendly waters. Many visitors enjoy birdwatching, trying local seafood, and strolling the waterfront parks.
How is the weather in Oak Island?
Oak Island experiences mild winters around 36–57°F (2–14°C) and humid summers near 73–90°F (23–32°C), with the most rain typically in late summer and early fall. Light layers work well, especially during outdoor activities.
What are the best places to visit in Oak Island?
Explore the Oak Island Lighthouse, waterfront parks, and local art galleries. Stroll sandy beaches or visit community fishing piers for classic coastal views.
What are some hiking trails in Oak Island?
Oak Island has nature paths in local parks, boardwalks near marshes, and easy walking trails by the beach. These spots feature native plants and coastal birdlife, creating a relaxed outdoor experience.
What are some family activities we can do in Oak Island?
Families frequently enjoy beach games, exploring tide pools, and visiting playgrounds near the shore. Kayaking and fishing are also popular ways to explore the coastal environment together.
What are some of the best day trip ideas from Oak Island?
Many guests explore historic downtown areas, scenic state parks, or coastal islands near Oak Island. Art museums and local markets in surrounding towns provide options for culture and shopping.
Are there any pet friendly accommodations available in Oak Island?
Pet-friendly vacation rentals are available in several Oak Island neighborhoods, especially near beaches and parks. Many hosts welcome dogs and provide convenient access to outdoor spaces.
What are some local tips for visiting Oak Island?
Bring sunscreen and bug spray for beach days, and follow posted rules in natural areas for wildlife protection. Reusable water bottles and beach shoes often make exploring local spots more comfortable.
What is Oak Island known for?
Oak Island is known for wide sandy beaches, the Oak Island Lighthouse, and a welcoming coastal atmosphere. Fishing, birdwatching, and seasonal seafood traditions are woven into local culture.
What are the best hidden gems to explore in Oak Island?
Visitors often discover quieter beach access points, local art studios, and marsh boardwalks. A few tucked-away cafes and small nature preserves showcase the area's relaxed coastal character.
What are the best foods to try in Oak Island?
Locally caught shrimp, seasonal blue crab, and fresh fish are frequently suggested. Southern-style hushpuppies and hand-churned ice cream from local stands are favorites among visitors.
What should I bring for a trip to Oak Island?
Pack swimwear, sandals, a sun hat, and light layers suited for shifting coastal temperatures. Bring insect repellent, reusable water bottles, and something for shade if you plan to spend time on the beach.
What is the nightlife in Oak Island like?
Oak Island has casual bars, laid-back taverns, and occasional live music at local venues. Evenings tend to be relaxed, with many guests enjoying waterfront dining and community hangouts.
What are the most popular events or festivals in Oak Island?
Oak Island's calendar has seasonal seafood celebrations, summer music nights, and craft markets, especially around long weekends and during warmer months. Community parades and beach-oriented activities are often popular with locals and visitors alike.
Are there family friendly vacation rentals in Oak Island?
Many Oak Island rentals welcome families, with options ranging from beachfront cottages to homes near parks and playgrounds. Hosts often provide amenities like kitchens and outdoor spaces for easy family gatherings.
When is the best time to visit Oak Island?
Spring and early fall are frequently suggested, with pleasant temperatures and lower humidity. Many visitors enjoy the warmer months for beach activities and seasonal festivities.
Quick stats about holiday rentals in Oak Island

Total holiday rentals
Explore 1,870 holiday rentals in Oak Island

Nightly prices starting at
Oak Island holiday rentals start at $39 SGD per night before taxes and fees

Verified guest reviews
Over 45,500 verified reviews to help you choose

Family-friendly holiday rentals
1,630 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 760 rentals that welcome pets

Holiday rentals with a pool
600 properties feature pools

Rentals with dedicated workspaces
750 properties have a dedicated workspace

Wifi availability
1,860 of Oak Island holiday rentals include wifi access

Popular amenities for guests
Guests love Beachfront, Gym and BBQ grill across Oak Island rentals

4.7 Average rating
Oak Island stays receive an average rating of 4.7 out of 5 from guests
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