Many of our esteemed Ocean Reef Resorts guests have discovered the secret: fall is the best time to visit The Emerald Coast. The season, affectionately termed "Sweater Season," is full of sunny, dry days and crisp, clear nights. Think pools heated to the perfect temperature, fire pits ablaze under starry skies, and gulf waters that still welcome swimmers. For those keen on sports, championship golf courses, and pro tennis centers offer special discounts for our guests. Plus, heavenly sunsets over the gulf and less crowded restaurants make the experience even more special. And to top it all off, vacation rental rates are incredibly reasonable.

But where should you stay to make the most of this epic fall season? Whether you're a couple seeking a romantic hideaway, a family in need of multiple bedrooms, or a group of friends looking for the perfect retreat, we've got you covered. Read on as we unveil 12 hand-picked Destin vacation homes that promise to elevate your fall break to a whole new level. From grand estates that can host your extended family to cozy havens, there's something for everyone.

Commander's Palace

10 Bedrooms / 10 Full & 2 Half Bathrooms / 32 Guests

Located in the heart of Destin's Crystal Beach, Commander's Palace is a grand ten-bedroom estate perfect for hosting large family reunions or multiple families, especially during Fall Break. This magnificent three-story home can accommodate up to 32 guests across the main house and guest house. The chic and trendy interiors are complemented by modern amenities, including a luxurious 32x29 swimming pool, soaking tub, and sun patio, making it an ideal spot for relaxation and entertainment. The home's proximity to the beach and local attractions like Destin Commons adds to its appeal, providing guests with easy access to shopping, dining, and more.

Soleil All Day

8 Bedrooms / 8 Full & 2 Half Bathrooms / 24 Guests

Nestled in Dune Allen Beach, only minutes east of Destin, Soleil All Day offers a lavish escape with eight bedrooms and accommodations for up to 24 guests, making it an ideal retreat for Fall Break. This newly built, contemporary 30A vacation home features a rooftop observation deck with stunning 360-degree views of the Gulf and a sparkling coastal dune lake. The private 20'x30' swimming pool and the inclusion of a six-seater golf cart and eight complimentary bicycles make beach access a breeze. The home's indoor and outdoor spaces, including a game room, multiple balconies, and luxurious bedrooms, are designed for comfort and style.

This home is also offered for sale by Ocean Reef Real Estate, presenting an exceptional investment opportunity with built-in property management through Ocean Reef Resorts. Learn more...

Tuscany

7 Bedrooms / 6 Full & 1 Half Bathrooms / 24 Guests

Vacation in style at Tuscany, a massive beachfront home in the exclusive Destiny by the Sea neighborhood, perfect for a luxurious Fall Break getaway. This seven-bedroom residence can host up to 24 guests and offers a private beach, a lagoon-shaped community pool, and luxurious interiors. The grand living areas, elegant furnishings, and panoramic Gulf views make Tuscany a prime choice for those seeking both comfort and luxury. The nearby attractions, including the iconic Crab Trap restaurant and the trendy Destin Commons, provide ample entertainment options for guests.

Watercolors

7 Bedrooms / 7 Full & 1 Half Bathrooms / 28 Guests

Watercolors is a stunning three-story vacation home in Destin's Miramar Beach, offering seven bedrooms and accommodations for up to 28 guests, making it an excellent choice for a Fall Break retreat. Perfect for large beach reunions, this home is located just three blocks from the beach and features a private 13x22 swimming pool that can be heated for cooler fall days, a pergola with a picnic table, and a gas grill for outdoor dining under crisp, clear skies. The home's open living spaces, coastal decor, and multiple balconies with Gulf views create an inviting atmosphere to enjoy the warm autumn sunsets and the tranquility of the season.

Beach House

6 Bedrooms / 6 Full & 3 Half Bathrooms / 20 Guests

True to its name, Beach House is a gorgeous six-bedroom, six-bathroom beachfront property in Destin's Miramar Beach, making it an ideal choice for a Fall Break getaway. With nearly 4,000 square feet of living space and the capacity to accommodate 20 guests, this home is perfect for entertaining large groups. The expansive balconies offer stunning Gulf views, and the home's interiors are designed with comfort and style in mind. The proximity to popular attractions like Silver Sands Premium Outlets and Seascape makes Beach House a favorite for repeat visitors.

Sugaree Sands

6 Bedrooms / 6 Full Bathrooms / 20 Guests

Sugaree Sands in Seagrove Beach is an ideal retreat for large groups, especially for a Fall Break escape. Offering two separate units with identical floorplans that can accommodate up to 20 guests, each unit features three bedrooms, three bathrooms, and an open living, dining, and kitchen area, making it perfect for multiple families or friends vacationing together. The property's private plunge pool, beach setup, and complimentary bikes enhance the beach experience, while the home's location along 30A in Seagrove Beach provides easy access to local dining and shopping.

Destin Condos Perfect for Fall

Craving the ultimate fall getaway? Look no further than Destin's luxury condos—where off-season means fewer crowds but all the amenities. Check out our top 10 condo picks for an unforgettable autumn escape.

Camelot

5 Bedrooms / 5 Full & 1 Half Bathrooms / 19 Guests

Experience unparalleled luxury at Camelot, a five-bedroom beachfront home in the exclusive Destiny by the Sea community. Accommodating up to 19 guests, this French Quarter-inspired residence offers stunning Gulf-front views, a private plunge pool, and lavish interiors. Each bedroom features an ensuite bath, and the home's multiple verandas provide perfect spots for enjoying the coastal scenery. Camelot’s prime location near popular beach bars, restaurants, and shopping makes it an ideal destination for a luxurious beachside escape. With its inviting spaces and scenic vistas, Camelot offers a dreamy setting for a memorable Fall Break.

Family Tides

5 Bedrooms / 4 Full & 1 Half Bathrooms / 14 Guests

Family Tides, located in the gated Destiny East neighborhood, is a spacious five-bedroom home perfect for beach reunions, accommodating up to 14 guests. With Fall Break in mind, this home offers primary suites on all three levels, each with luxurious ensuite baths, providing comfort and privacy for all guests. Easy access to the beach and community amenities like a large pool, hot tub, and fitness center ensures everyone has something to enjoy. The comfortable and well-appointed interiors, combined with the proximity to local attractions, make Family Tides a top choice for families and groups looking to make the most of their autumn getaway.

Day Dreamer

4 Bedrooms / 5 Full Bathrooms / 12 Guests

Day Dreamer in Seagrove Beach is a modern vacation home that lives up to its name, providing a dreamy escape for up to 12 guests. Perfect for a Fall Break retreat, this stylish home is just 150 yards from the beach and features a private pool, a rooftop sundeck with a fire pit, and vibrant mid-century modern decor. Each bedroom is equipped with a king-sized bed and an ensuite bathroom, ensuring comfort for all guests. The home's location near Seaside and other 30A hotspots makes it an ideal base for exploring the area during the crisp autumn days.

Rising Tide

4 Bedrooms / 2 Full Bathrooms / 10 Guests

Rising Tide is a pet-friendly, lakefront vacation home in Dune Allen Beach with four bedrooms and accommodations for 10 guests, making it an excellent choice for a Fall Break getaway. The home's wraparound deck offers stunning views of Oyster Lake and the Gulf, while the lagoon-shaped private pool and hot tub provide relaxation and entertainment. The property's proximity to local dining and shopping, as well as the unique coastal dune lake setting, makes Rising Tide a perfect retreat for nature lovers and beach enthusiasts looking to enjoy the beauty of the season.

Destin2bHere

3 Bedrooms / 4 Full Bathrooms / 10 Guests

Destin2bHere is a stylish lakefront home in Destin's Kokomo Kove, accommodating up to 10 guests, making it an ideal choice for a Fall Break retreat. This three-story residence features a saltwater swimming pool, a state-of-the-art kitchen, and multiple balconies with serene views of the lake. The home's chic coastal decor and proximity to the beach, as well as popular local attractions, make it a perfect spot for a relaxed and enjoyable autumn vacation.

Painted Porch

Painted Porch in Frangista Beach is a charming, classic home perfect for small groups or families, accommodating up to seven guests. The home features a private plunge pool surrounded by a tropical patio, vibrant decor with a Floridian flair, and three cozy bedrooms. Located just four blocks from the beach, Painted Porch offers easy access to local restaurants, shopping, and entertainment, making it a delightful choice for a beach vacation—especially during Fall Break.

Discover your perfect fall break destination among these twelve exceptional Destin vacation homes, accommodating anywhere from eight to thirty-two fortunate guests. Whether you're drawn to a cozy beach cottage or an opulent villa, you'll find an array of sizes, styles, and settings tailored to your group's needs. Our cutting-edge Ocean Reef Resorts website offers detailed descriptions, vibrant property images, aerial views, and real-time seasonal rental rates and availability calendars to assist you in making the best choice. Don't miss out on the opportunity to experience the ultimate fall beach vacation—these sought-after properties book up quickly. Act now to secure your dream autumn getaway and prepare for an experience you won't soon forget.

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