Want to ditch the heavy coat and soggy boots? How about waking up in the lap of Southern luxury, surrounded by breathtaking beauty, history, and shockingly warm weather? From grand Southern estates in South Carolina to contemporary penthouses overlooking the breathtaking Florida beaches, these vacation rentals are reserved for those who seek nothing but the finest.
Whether you’re an adventurous soul with a taste for luxury or an avid aficionado of Southern splendor, these are the best Southern vacation rentals for a winter getaway.
An Entire Private Island, Crescent Island, Florida
- Location: Crescent Island, Florida
- Sleeps: 12
- Price per night: $1,870+
If utmost seclusion is your priority, ask Santa to book a trip to this high-end vacation rental. Imagine a retreat where water acts as a natural barrier, ensuring your complete privacy and where space abounds for your extended family. Situated on a secluded four-acre island in the heart of Sanibel, Florida, this expansive four-bedroom, three-level residence features a screened deck adjoining the living area, a recreational room, and a private dock granting direct access to both the Gulf and the Intracoastal waterways.
The Citrus Beach Club, Ocean Isle Beach, North Carolina
- Location: Ocean Isle Beach, North Carolina
- Sleeps: 16+
- Price per night: $1,283+
If you’re craving a winter escape, experience coastal luxury at its finest at the Citrus Beach Club, Ocean Isle Beach’s premier oceanfront retreat. With nine bedrooms and 9.5 bathrooms, this spacious haven is tailor-made for large family gatherings. Step outside to discover a pristine pool area, hot tub, an outdoor bar and lounge with a cozy fire pit, and private beach access. The main floor features an open-concept design with a chef’s kitchen, a 20-foot glass door system framing stunning ocean views, and four bedrooms with en-suite bathrooms. Upstairs, five additional bedrooms include three master suites with ocean-facing balconies, so you can take your whole family.
Year-Round Escape at Hilton Head Island, South Carolina
- Location: Hilton Head Island, South Carolina
- Sleeps: 15+
- Price per night: $1,940+
Escape to this luxurious beach rental featuring stunning island views. Perfect for any time of year, this rental includes everything you need for boating, kayaking, paddle boarding, dolphin watching, and crabbing. Relax by the pool, gather around the fire pit, or enjoy the extensive game room with pool and ping pong tables, gaming, and more. Additional amenities include a gym, massage table, a deluxe $3,000 massage chair, and a piano. Located just minutes from Savannah, you can also use this rental as a launchpad for all your southern day trips.
Gulf Coast Dream in Inlet, Florida
- Location: Inlet, Florida
- Sleeps: 16+
- Price per night: $2,229+
If you’re hunting for warm weather for your winter vacation, then come experience the ultimate beachfront getaway just steps from Inlet Beach’s crystal blue waters. Whether you’re hosting a large family gathering or vacationing with friends, this spacious retreat comfortably sleeps 18 guests. At the end of the day, relax by the rooftop pool with breathtaking panoramic views of one of the best beaches in America. Just a stone’s throw away from Camp Helen State Park, the property is conveniently located within walking distance of shopping, golf courses, dining, outdoor activities, and the beautiful white sand beaches of the Gulf shores. You can have your feet in the sand in just 60 seconds from this home.
Historic Vacation Home in Charleston, South Carolina
- Location: Charleston, South Carolina
- Sleeps: 16+
- Price per night: $571+
If you’re craving a winter getaway sans snow, indulge in luxury in this three-story home in Charleston’s French Quarter. Featured in Charleston Home + Design Magazine, this condo accommodates up to 16 guests and sits just minutes from the Atlantic Ocean. Take a stroll to the city market, or go biking to local beaches and breweries. The living space boasts exposed interior brick, original heart pine hardwood floors, a gourmet kitchen, and ample seating for entertaining. Enjoy the best of Charleston in this opulent retreat.
Southern Comfort in Fairhope, Alabama
- Location: Fairhope, Alabama
- Sleeps: 10
- Price per night: $1,063+
It won’t be a typical Christmas, but this charming Southern home, nestled among majestic live oak trees, offers a serene retreat for the winter months. A short stroll brings you to Mobile Bay, perfect for watching stunning sunsets and native birds. The home features six bedrooms and six bathrooms, with two main suites on the first floor and additional bedrooms, each with twin beds. The spacious kitchen, formal dining area, and generous great room provide ample gathering space. Enjoy the peaceful open porch with rockers and a porch swing.
Luxury Lodge in Ellijay, Georgia
- Location: Ellijay, Georgia
- Sleeps: 16+
- Price per night: $1,084+
Perfect for outdoor enthusiasts, this private mountain oasis offers a luxurious retreat with numerous bedrooms, ample bathrooms, and many amenities. The Lodge and Bunkhouse feature spacious living areas, a gourmet kitchen, and inviting porches. Ideal for corporate retreats, weddings, family getaways, and more, the property boasts a private 18-hole disc golf course, hiking trails, nearby wineries and breweries, and outdoor adventures at the adjacent national parks. There’s no off-season when you’re in this sort of natural beauty.
Stylish Home in San Antonio, Texas
- Location: San Antonio, Texas
- Sleeps: 16+
- Price: $799+
Nestled on a sprawling 4-acre estate, this luxurious and stylish getaway offers an expansive 6,500 square feet of space to indulge in. It’s perfectly located for your group’s enjoyment, just a stone’s throw away from popular attractions like The Rim, Six Flags, and the San Antonio hot springs. The resort-style pool, complete with a hot tub and kiddie pool, beckons you to unwind. With its spaciousness, upscale amenities, and inviting outdoor area, this estate is your ultimate destination for relaxation and recreation. Your group’s dream getaway awaits!
Luxe Retreat in Gatlinburg, Tennessee
- Location: Gatlinburg, Tennessee
- Sleeps: 12
- Price: $957+
This newly built retreat boasts an array of winter activities that promise an unforgettable Smoky Mountain vacation. Go snowmobiling in the park, relax in the hot tub, or take a drive up to Nashville for some good live music. The massive kitchen is a chef’s dream, and you won’t tire of this winter wonderland view, making it a cozy getaway for couples, families, gatherings, and retreats, ensuring your stay is nothing short of extraordinary.
Rustic Cabin in Mineral Bluff, Georgia
- Location: Mineral Bluff, Georgia
- Sleeps: 12
- Price: $607+
Indulge in the luxury of this custom-built mountain lodge nestled along the picturesque Toccoa River and minutes from the Blue Ridge mountains. Perfect for adventurous snowbirds who want to relish in the beauty around them, this upscale retreat offers plush comfort and stunning riverfront views. Whether relaxing by the fireplace, stargazing in the hot tub, or fishing off the backyard riverbank, this lodge promises unforgettable moments.
As winter brings the South a gentle chill, these enchanting vacation rentals offer a warm embrace and a chance for truly cherished memories. Whether you seek solace in the snowy mountains or a cozy coastal hideaway, these handpicked Southern gems provide the perfect backdrop for your winter escape or an exciting opportunity to invest in a year-round destination. Arrived offers the opportunity to invest in vacation rentals like these nationwide with a lower minimum investment threshold and an easy signup process.
The opinions expressed in this article are for general informational purposes only and are not intended to provide specific advice or recommendations for any individual or on any specific security or investment product. The views reflected in the commentary are subject to change at any time without notice. View Arrived’s disclaimers.
