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6 Dec 2023
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Oak Island Trip Planning

As temperatures drop, the days shorten, and we all spend more time indoors, coastal Carolina enjoys milder temperatures and weather. Average highs around Thanksgiving and Christmas range from 59°F to 65°F, with lows varying from 42°F to 47°F. Beautiful beaches and the prevalence of large, single-family homes for rent make the Oak Island and Southport area a great destination to gather the gang for "Christmas on the Beach," celebrate Hannukah, or ring in the New Year.

Our collection of spacious, meal-making friendly homes offer the seclusion, comfort, and roominess you need for a safe and relaxing holiday that reunites the family and allows everyone to spread out.

Your Caswell Beach Home-Away-from-Home for the Holidays

Vacation rentals with 3+ bedrooms are ideal for small to larger families with those rentals of 4+ bedrooms giving you, the grandparents, and a few others enough area to share indoor spaces comfortably. A home with equipped kitchens and ample dining and common spaces provide the perfect basecamp to cook memorable meals and make merry with loved ones.

Read on for just a few suggestions you'll find along Caswell Beach.

Poolside Paradise

poolside paradise oceanfront caswell beach oak island private pool

6 BR | 4.5 BA | Sleeps 13

Bedding: 1 King, 3 Queens, 2 Doubles, 1 Twin

Enjoy the holidays while watching the sun set from Poolside Paradise’s private, heated pool this season! This gorgeous oceanfront 6-bedroom offers guests an expansive floorplan with large, covered porches and an oceanfront pergola. Take advantage of the heated pool service during the cooler months by adding it to your folio!

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Sea Turtle

sea turtle oak island caswell beach vacation rental

7 BR | 6 BA (3 Full, 3 Half) | Sleeps 16

Bedding: 3 Kings, 4 Queens, 2 Twins

Expansive, panoramic views and ample space for meals, games, and indoor relaxation make this 7-bedroom home a perfect spot to celebrate the holidays. Set along the pristine shores of Caswell Beach, this amenity-rich 7-bedroom boasts unobstructed views of the Atlantic as well as an amazing panoramic of the waterway into Southport. Sea Turtle finds itself just far enough from the hustle and bustle to provide a secluded getaway while still being close enough to all of the shopping and restaurants that East Beach offers.

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Captain’s Choice

captains choice oak island caswell beach vacation rental large

8 BR | 7.5 BA | Sleeps 20

Bedding: 3 Kings, 7 Queens

Ideal for large family gatherings, this stately 8-bedroom oceanfront home features 2 living areas, and massive, vaulted ceilings. High-touch amenities, like a wine cooler and fully equipped kitchen, make for enhanced merrymaking. When it's time for a refreshing beach stroll to watch the sunrise or the dolphins, the private 147-foot walkway to the strand is an incredible amenity. You'll truly be able to relax at Captain's Choice.

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161 Fairway

161 fairway caswell beach caswell dunes oak island golf course vacation rental

3 BR | 2 BA | Sleeps 10

Bedding: 1 King, 2 Queens, 2 Sets of Bunkbeds

161 Fairway is an adorable coastal home located along the Oak Island Golf Course. The spacious accommodation offered includes an open floorplan living, dining and kitchen area, an additional upper-level loft area with a seating area and 2 sets of bunk beds, and 3 additional comfortable bedrooms. Enjoy a morning cup of coffee and croissant from the bright and airy sunroom. Take the private golf cart out for a morning drive around the Arboretum, or head over to the beach for a day on the sand. Conveniently located in the Caswell Dunes neighborhood, guests can take advantage of shopping, restaurant and grocery establishments nearby while avoiding the parking and traffic congestion.

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Sea Winds

sea winds private pool oceanfront caswell beach vacation rental

5 BR | 3 BA | Sleeps 13

Bedding: 3 Kings, 3 Doubles, 1 Twin

Gorgeous views of the Atlantic and an amazing, picturesque view of the Oak Island Lighthouse decked out in its holiday lights await you and your family this season! An oceanfront beauty, Sea Winds is a 5-bedroom property offering numerous updates and a peaceful setting where you and your family can make memories that will last a lifetime!

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Spend Your Holiday on Caswell Beach

Didn't see a property that suits your needs or your travel timeframe? Need a property just a bit smaller for a more cozier Caswell Beach stay? The reservations staff of Margaret Rudd & Associates is available 7 days per week to assist you in your vacation planning. Simply call our office at (800) 486-5441 or email us at for assistance.