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Rosemary Beach® vacation rentals offer a delightful way for families and friends to enjoy the beauty of the Emerald Coast in an elegant and harmonious setting.

Rosemary Beach

78 N Barrett Square, Unit B

Rosemary Beach, FL 32461

Rosemary Beach® Winter Rentals

Winter in the Rosemary Beach community is a wonderland of white sand beaches, sparkling turquoise waters, and sun-kissed days. Modeled in simplistic elegance with a coastal touch, our Rosemary Beach community winter rentals are the perfect winter escape to the natural splendor of Florida’s Emerald Coast. From lush studio carriage houses to multilevel beach cottages, our winter Rosemary Beach house rentals offer luxurious amenities with the familiar comforts of home for your escape to paradise. Read on to learn more about our Rosemary Beach winter rentals!

Features and Amenities of Our Winter Rentals

Whether you seek a couple’s retreat in an intimate carriage house or a family winter break in an upscale loft, each of our Rosemary Beach winter rentals is fully furnished with all essentials and added touches to enhance your stay.

Bright, airy living rooms and lounge areas are amplified by warm natural lighting, highlighting the coastal contemporary finishes of the every rental. Unwind on plush furnishings with a movie on flat screen TVs, and stay connected with complimentary Wi-Fi, included in select winter rentals.

Open floor plans allow you to prepare a meal while enjoying the company of your family and friends in adjoining living rooms and dining rooms. Our gourmet kitchens are fully equipped with modern appliances and cooking essentials so you can prepare a simple coffee and toast in the morning or a full breakfast with pancakes.

Spacious bedrooms range from luxe master suites and king or queen guest bedrooms to fun bunkbeds for the kids. Spa-quality bathrooms feature glass-door walk-in showers or sunken tubs for an indulgent soak at the end of the day. Enjoy the spectacular gulf coast sunset from your own private balcony in our Gulf front winter rentals, or warm up from the chill of the winter night with your private outdoor fire pit.

Many of our homes for rent in Rosemary Beach FL include complimentary amenities such as bicycles and community pools.

Things to Do in Winter

Visiting in winter means enjoying the sand to yourself with less crowds and low rates. December illuminates the Rosemary Beach community in a spectacle of lights and beautiful decorations, heralding the holiday season. New Year’s celebrations bring incredible firework shows, outdoor concerts, and exceptional dinner experiences in the fabulous restaurants in the Rosemary Beach community. In January, catch the 30A Songwriters Festival, a three-day event drawing world-class performers from around the country to showcase their talents at intimate venues across the region. If you’re craving a unique culinary adventure, mark your calendar for the Sandestin Gumbo Festival in February.

Ready to make your winter escape to Florida? Contact us today to book your own Rosemary Beach house rentals!

Spend your winters in paradise with our Rosemary Beach winter rentals! Call (855) 430-1741 for more details or to reserve today.  Fitness Center Monthly Membership: Single $125  |  Couple $162  |  Family of 4 $266

Carriage Houses


  • Four Stars Flat – Parkside – Two Bedroom /  Two Bath – $2,145++
  • Gracelyn Flat – Parkside – Two Bedroom / Two Bath – $2,420++
  • This N That Flat – Parkside – Two Bedroom / Two Bath – $2,500++ (December, January & February) 
  • Rene Flat – Parkside – Two Bedroom / Two Bath – $2,677++
  • MALO Flat – Parkside – Two Bedroom / Two Bath – $3,190++


  • Coastal Loft – Parkside – Two Bedroom / Two Bath – $3,080++
  • Tabby Loft – Parkside – Two Bedroom / Two Bath – $3,080++  (December & February Only) 
  • Paradise Loft – Parkside – Three Bedroom / Two Bath – $3,080++  (December & January Only) 
  • Sprig Loft – Parkside – Two Bedroom / Two Bath – $3,612++


  • Ciao Bella – Seacrest Beach – Three Bedroom / Three Bath – $3,300++
  • Mannion Cottage – Two Bedroom/Three Bath – $3,300++
  • Java Cottage – Parkside – Two Bedrooms/ Two and a Half Baths – $3,956++ (January  Only)
  • Barbados Cottage – Parkside – Two Bedroom / Two and a Half Bath – $3,423++
  • McIntyre Cottage – Parkside – Three Bedroom / Three Bath – $3,850++
  • Caspian Dream – Seacrest Beach –  Three Bedroom / Three Bath – $3,868++
  • In the Pocket Cottage – Parkside – 3 Bedroom/Two and a Half Bath – $3,960++
  • Marshall Cottage – Seacrest Beach – Three Bedroom / Three and a Half Bath – $4,180
  • Trachte Cottage – Parkside – Three Bedroom / Two and a Half Bath – $4,400++ (February Only)
  • Wright Cottage – Parkside – Three Bedroom/ Three Bath – $4,804++ (December & January Only) 
  • Tonic Cottage – Parkside – Four Bedroom / Four and a Half Bath – $4,920++
  • Southern Comfort Cottage – Parkside – Four  Bedroom / Three and a Half Bath – $5,170++
  • Peace Townhouse – Parkside – Five Bedroom /  Four and a Half Bath – $5,280++  (January & February Only)
  • Sunshine Daydream Cottage – Parkside/Luxury Collection – Three Bedroom/ Three Bath – $12,100 (January & February Only)
Disclaimer: Prices displayed do not include taxes or departure deep cleaning fees. 
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