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2 Dec 2021
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Oak Island Trip Planning

Whether this will be your first winter "flying south" or you're looking to try out a new winter home for a month or so, Oak Island, NC should be on your shortlist of snowbird destinations. Not only is the weather mild with highs in the upper 50s to mid-60s November through February with an average of 6 days of rain per month, but there's also no shortage of outdoor and indoor diversions.

Stroll the pristine sands, read a book while enjoying gorgeous ocean views, hit the links for a quick 18 holes or enjoy the close locale to Southport's charming shops and restaurants.

Oak Island is an up-and-coming destination to nest during the off-season, a place where you're more likely to enjoy fewer winter crowds and better prices than that of Florida, Myrtle Beach, or the Texas/Bama Gulf Coast.

Popular Snowbird Rentals in Oak Island-Southport, NC

10 Pinehurst
snowbird rentals oak island

3 Bedrooms | 2 Bathrooms | Sleeps 6

This charming, second-level 3 bed, 3 bath condo is located on Caswell Beach and provides gorgeous ocean views, onsite access to the Oak Island Golf Course, and convenient access to the strand. Top features include a furnished deck and screened-in porch, as well as recently added brand new wood flooring in the living area and hallway, new 43-inch TV, and new bedroom furnishings. A newly renovated kitchen makes preparing meals a delight, and a ground-level grill is also available. 

Featured Amenities:

  • Screened/Covered Porch
  • Wi-Fi
  • Washer/Dryer

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Aunt Evelyn’s 
winter snowbird rentals in southport nc

3 Bedrooms | 3 Bathrooms | Sleeps 6

Supplying exceptional views of the Southport Marina and an unbeatable location, Aunt Evelyn's is the perfect winter getaway for snowbirds. Relax in the beautifully appointed 3-bed, 3 bath condo before heading downtown for a taste of Southport's fantastic restaurants, hours of strolling the live oak-lined historic streets, and shopping. If you're craving a walk along the beach, Oak Island's strand is just a 10-minute drive away.

Featured Amenities:

  • Covered Porch
  • Charcoal Grill
  • Wi-Fi
  • Washer/Dryer

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Sea Turtle
Sea Turtle Oceanfront Caswell Beach Property

7 Bedrooms | 5 Bathrooms | Sleeps 15

An entire month of unobstructed ocean views and panoramic views of the waterway into Southport can’t be beaten for your winter home-away-from-home. This newly renovated and amenity-rich 7 bedroom provides more than enough space, offers a lower-level game room, expansive living areas, and a comfortable covered porch perfect for entertaining during the holidays!

Featured Amenities:

  • Oceanfront
  • Game Room
  • Covered Porch
  • Open Deck

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Sandy Cheeks
long term winter rentals in oak island nc

4 Bedrooms | 3.5 Bathrooms | Sleeps 12

Sandy Cheeks is a spacious four-bed, 3.5 bath home located along the East Beach of Oak Island. Top features include beautiful hardwood floors, a gourmet kitchen with modern appliances, and granite countertops. Perfect for winter snowbirds, this home also includes an elevator that provides access to the main floor plan and shared living space. Enjoy unobstructed ocean views from the upper or lower porches. Be sure to invite the whole clan to visit while you winter on Oak Island. Sandy Cheeks offers oodles of entertainment, including board games and puzzles.

Featured Amenities:

  • Covered Porch
  • Beach Chairs & Umbrella
  • Outdoor Shower
  • Wi-Fi
  • Board games/puzzles
  • Cable/DVD Player/Surround Sound

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ForeShore
winter rentals in oak island nc, foreshore vacation rental rudd

4 Bedrooms | 2.5 Bathrooms | Sleeps 8

ForeShore is a beautiful 4-bed, 2.5 bath 2nd-row beach cottage in the East Beach area of Oak Island. This home features an inverted floor plan, meaning the main living space (kitchen, living room and dining) is on the top floor where the views are best. While the indoor amenities are numerous, its absolute best feature is an abundance of outdoor decks and porches with both views of the ocean (for sunrise) and the marsh (for sunset).

With winter temperatures hovering around 60°F, dining on the ample deck space is a delight. There is plenty of seating with new picnic tables and seating.

Featured Amenities:

  • Covered Porch
  • Beach Toys
  • Outdoor Shower
  • Wi-Fi
  • Video Library
  • Book Library
  • Board Games/Puzzles

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Choosing Your Oak Island Snowbird Rental

If you're not sure which monthly snowbird rental is right for you, don't fret. The experts at Margaret Rudd & Associates' Oak Island are here to help. Call us at (800) 486-5441. Our reservation specialists are happy to assist you in finding the perfect vacation rental to suit your budget, beach accessibility, amenity preferences, and if you're looking for a pet-friendly snowbird rental.

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