Dreaming of a serene winter beach escape? Destin and 30A offer the perfect backdrop for a rejuvenating retreat with stunning Gulf views, mild weather, and charming coastal communities. Our featured collection of monthly winter rentals in Destin & 30A ranges from cozy two-bedroom retreats for six to expansive five-bedroom homes accommodating up to 18 guests—perfect for hosting family and friends or enjoying a quiet extended getaway.

With thoughtfully designed interiors, inviting outdoor spaces, and prime locations near world-class dining, shopping, and entertainment, each rental property is equipped for comfort and convenience. Professionally managed by Ocean Reef Resorts, these homes ensure a worry-free experience, letting you fully unwind and embrace the magic of Florida's Emerald Coast. 

Start planning your winter getaway today!

Tipsy Marlin

2 Bedrooms / 2 Full Bathrooms / 6 Guests

Located in Blue Mountain Beach, Tipsy Marlin is a charming two-bedroom pet-friendly beach house perfect for family getaways or as a monthly winter rental. This home features two inviting porches, a spacious open living area with bright beachy decor, and a fully equipped kitchen. Upstairs, the primary suite includes balcony access, while a second cozy queen bedroom is nearby. The home offers outdoor grilling and a prime location just steps from Scenic 30A and the Gulf. Guests can enjoy nearby restaurants, activities, and the tranquil vibe of Blue Mountain Beach.

Inlet Beach Dream

2 Bedrooms / 3 Full Bathrooms / 6 Guests

Soak up Gulf views and the refreshing 30A breeze from Inlet Beach Dream, a raised three-story vacation home ideal for up to six guests and perfect as a monthly winter rental. This home features a spacious second-floor living area with sunny windows, an open kitchen, and a breezy Gulf-view balcony. The primary suite encompasses the entire third floor, offering a tropical-style king bedroom with an ensuite bath. The fourth floor includes a cozy queen loft bedroom with a private balcony for breathtaking Gulf views. Enjoy outdoor dining at the ground-level BBQ area and explore nearby attractions like 30Avenue, Rosemary Beach, and Camp Helen State Park, all just minutes away.

Beach Buddy

3 Bedrooms / 2 Full Bathrooms / 8 Guests

Located in Gulfview Heights, Beach Buddy is a charming three-bedroom retreat that sleeps eight and is perfect for a monthly winter rental. Just a short stroll from the Gulf and Draper Lake, this home features a private pool with a spacious patio, a wraparound balcony, and an open living and dining area with vaulted ceilings and natural light. The primary bedroom includes a queen bed and ensuite bath, while two guest rooms offer additional queen and twin accommodations. Enjoy nearby Gulf Place with its restaurants, shops, and events, making Beach Buddy an ideal 30A getaway.

Panorama

3 Bedrooms / 3 Full Bathrooms / 10 Guests

Located in the heart of Destin's Miramar Beach, Panorama is a three-bedroom vacation home that comfortably sleeps ten guests and is ideal for a monthly winter rental. This property features a private 30' x 15' seasonally heated pool (for a fee), a rooftop observation deck with Gulf views, and access to a lagoon-shaped community pool overlooking the beach. The open living area is perfect for gatherings, with a queen sleeper sofa and fully equipped kitchen. The primary suite boasts a king bed, twin daybed, and trundle, while two guest rooms offer queen beds, one with a balcony. Enjoy proximity to Gulf-front dining, Silver Sands, and Baytowne Wharf for the ultimate Destin escape.

Karen's Beach House

4 Bedrooms / 4 Full & 1 Half Bathrooms / 8 Guests

Nestled in the gated Caribe enclave of Miramar Beach, Karen's Beach House is a stately four-bedroom retreat that sleeps up to eight guests and is ideal for a monthly winter rental. This Mediterranean-style home offers serene lake views, private neighborhood beach access, and luxurious amenities, including two community pools and a tennis court. The main level features two primary suites, while upstairs includes a queen guest room with a balcony, a twin bedroom, and a cozy den. A third-floor loft with a wet bar and observation deck completes this elegant residence. Enjoy nearby dining, shopping, and attractions for a perfect Destin escape.

Mario Cottage

4 Bedrooms / 3 Full Bathrooms / 12 Guests

Located just two blocks from the beach, Mario Cottage is a charming three-story Crystal Beach vacation home that accommodates up to 12 guests and is ideal for a monthly winter rental. The home features a bright, coastal interior, an open living space, and a fully equipped kitchen. The primary suite includes a king bed, sleeper sofa, and private balcony, while additional bedrooms offer versatile sleeping arrangements, including a cozy loft with treetop views. Guests can enjoy a private lagoon-style pool, sand volleyball court, and proximity to dining, shopping, and attractions for a quintessential Destin getaway.

Sand Dollar

4 Bedrooms / 3 Full Bathrooms / 12 Guests

Tucked in historic Grayton Beach, Sand Dollar is a charming four-bedroom home accommodating up to 12 guests, perfect for a monthly winter rental. Just a three-minute stroll to the Gulf, this home features a private lagoon-style pool, a covered terrace for outdoor dining, and a wraparound balcony overlooking the pool. The main level includes three cozy guest rooms, while the spacious primary suite occupies the top floor with a king bed, sitting area, and luxurious ensuite bath. Enjoy nearby Grayton Beach State Park, local dining at The Red Bar, and the vibrant atmosphere of Scenic 30A for an unforgettable coastal escape.

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Curious about what makes Destin magical in December? From festive holiday events to breathtaking sunsets and unbeatable shopping, discover why winter on the Emerald Coast is a must-experience. Explore our guide to seasonal highlights and start planning your perfect getaway today!

Hemingway at 30A

4 Bedrooms / 4 Full Bathrooms / 12 Guests

Experience Old Florida charm with modern comforts at Hemingway at 30A, a four-bedroom home accommodating up to 12 guests, ideal for a monthly winter rental. Located in Seacrest Beach North, this property boasts access to interconnected pools with cascading waterfalls, a community tram to the nearby beach, and eight bicycles for exploring the area. The main house features a bright, open living area, a primary suite with a balcony, and two queen guest rooms. A separate carriage house offers added privacy with a queen bedroom, full kitchen, and living area. Close to Rosemary Beach and local dining, this home is perfect for a serene getaway.

Five O'Clock Somewhere

4 Bedrooms / 4 Full & 1 Half Bathrooms / 12 Guests

Nestled in the Summers Edge community of Seagrove Beach, Five O’Clock Somewhere is a cheerful Old Florida-style vacation home perfect for up to 12 guests and available as a monthly winter rental. This charming three-story property features four bedrooms, an open living area with coastal decor, and a spacious veranda overlooking lush magnolias. The primary suite occupies the top floor with a private balcony and ensuite bath. Guests can enjoy the nearby beach, a rare coastal dune lake, and two community pools, one seasonally heated. Close to dining, shopping, and outdoor adventures, this home is an idyllic retreat for any season.

Toes in the Sand

4 Bedrooms / 4 Full Bathrooms / 16 Guests

Located in Destin's Crystal Beach community, Toes in the Sand is a charming Old Florida-style vacation home ideal for up to 16 guests and perfect for a monthly winter rental. This property features a two-story main house and a poolside guest house, complete with a private swimming pool and multiple verandas. The main house includes an open living area, a spacious primary suite with a balcony, and two guest rooms, while the guest house offers additional living space, a king bedroom, and a kitchenette. Just minutes from the beach, dining, shopping, and entertainment, this home is the ultimate coastal retreat.

Sunset Beach

5 Bedrooms / 4 Full Bathrooms / 16 Guests

Located in a private neighborhood in Miramar Beach, Sunset Beach is a stunning five-bedroom home that accommodates up to 16 guests and is perfect for a monthly winter rental. This property features a lagoon-style pool with a Tiki Bar, sun deck, and entertainment system, making it a true tropical retreat. The elegant interior includes an open living area, a modern kitchen, and beautifully appointed bedrooms, including two luxurious primary suites with king beds and private balconies. Just a short stroll to the beach and close to dining, shopping, and attractions like Silver Sands, this home offers the ultimate coastal experience.

Crawdaddy's Casa

5 Bedrooms / 3 Full & 1 Half Bathrooms / 18 Guests

Located in Dune Allen Beach, Crawdaddy's Casa is a spacious five-bedroom retreat accommodating up to 18 guests, ideal for a monthly winter rental. This half-acre property features stunning Allen Lake views, a private 35'x15' pool with a shaded deck, and a screened-in porch perfect for dining or relaxing. Inside, the open floor plan includes a chef’s kitchen, multiple dining spaces, and a cozy living area. The home offers luxurious sleeping arrangements, including a master suite with a soaking tub and rain shower, plus a bunk room for the kids. Steps from beach access and close to local dining like Stinky’s Fish Camp, this home is a perfect Emerald Coast getaway.

Ready to escape to the Emerald Coast this winter? Explore our diverse collection of Destin and 30A monthly rentals to find the perfect home for your extended getaway. With Ocean Reef Resorts, your dream coastal retreat is just a booking away. Reserve your winter escape today and make memories that will last a lifetime!