Epic Fall Break Destin Vacation Homes

10 Top Picks for Your Ultimate Destin Autumn Getaway

Posted on 9/1/2023

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 10 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.

Once Upon A Tide

6 Bedrooms / 7 Full & 1 Half Bathrooms / 32 Guests

Welcome to Once Upon a Tide, your dream destination for an epic fall break. Nestled in the esteemed Frangista Beach community, this spacious six-bedroom Destin vacation home can accommodate up to thirty-two guests—ideal for large family reunions or friend getaways. With living spaces spread across three levels, it offers something for everyone. The first-floor Game Room, complete with a built-in bar and flat-screen TV, serves as your hub for autumnal relaxation. Step outside to enjoy the private swimming pool, hot tub, or gather around the fire pit on cooler nights for an intimate stargazing session. Multiple verandas and a rooftop Observation Tower provide various vantage points for soaking in the season's crisp air and stunning vistas, including glimpses of the gulf. Exclusive gated access to the shores of Frangista Beach and a community pool in a lush tropical setting add the finishing touches to this fall paradise.

Ideal Beach Destination

Ideal Beach Destination Destin

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

For a private yet luxurious fall escape, look no further than Ideal Beach Destination, a regal three-story villa situated in the highly exclusive, gated Destiny by the Sea community in Destin. Perfectly accommodating up to fourteen guests across its five lavish bedrooms, this vacation home is the epitome of autumnal opulence. A complimentary six-seater golf cart makes beach access effortless, but if you prefer a more personal setting, the home's own pool offers a secluded space for autumn swims. As the sun sets, perhaps take a short stroll to The Crab Trap, a local gulf-front restaurant just minutes away, or simply unwind in the community's simmering hot tub. The neighborhood's lagoon-shaped swimming pool, surrounded by tropical foliage, provides yet another option for relaxation. With so many choices for fall-friendly activities in and around this villa, "Ideal Beach Destination" truly lives up to its name for those looking to experience an unforgettable fall break.

Grayt Oasis

Grayt Oasis 30A

5 Bedrooms / 5 Full & 1 Half Bathrooms / 12 Guests

For a fall break vacation that combines outdoor adventure with a cozy community atmosphere, consider booking your stay at Grayt Oasis, a remarkable five-bedroom 30A rental home situated in the picturesque lakefront enclave of Grayton Landing. This property comfortably accommodates up to twelve guests and offers the perfect blend of relaxation and entertainment. Take advantage of the columned verandas on two upper levels or ascend to the rooftop deck to catch sweeping views that become all the more magical as hints of autumn colors take over. The lower level serves as your entertainment hub, featuring seating, a wet bar, and a mini-refrigerator. Its view overlooks a rare coastal dune lake, teeming with wildlife, and is adjacent to a community pool and an outdoor kitchen pavilion perfect for waterfront dining in the crisp fall air. For those who want to explore, the home is just a stroll away from both the award-winning Grayton Beach State Park and the historic village center of Grayton Beach—offering everything from live music at the famous Red Bar to paddleboard launches from a neighborhood dock. With such a variety of fall-friendly activities and amenities, "Grayt Oasis" promises an unforgettable autumn escape.

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Grayton Beach Walking Tour

There are plenty of forested paths, but honestly, how many trees can you pass before you need a little change of scenery? If you are searching for an even more unique experience, consider a stroll through the historic 30A town of Grayton Beach.

Paradise Villa

Paradise Villa Destin

4 Bedrooms / 4 Full & 1 Half Bathrooms / 20 Guests

For those in pursuit of an opulent fall getaway that comfortably accommodates a larger group, Paradise Villa in the heart of Destin's Miramar Beach promises an experience that lives up to its name. Picture waking up to the tranquil view of a natural lagoon, a visual treat amplified by the subtle changing colors of autumn foliage. This luxurious vacation villa offers room for up to 20 guests, featuring four elegant bedrooms—each with en-suite baths—plus multiple levels of outdoor space designed to immerse you in the scenic beauty of the Emerald Coast. Spend your days lounging poolside, or cooking up fresh seafood meals on the second-story balcony with a gas grill and ample seating, all set against the backdrop of a glistening lagoon. If the beach calls, you're granted full access to the Crescent condo complex, which features two beachfront pools, a soothing hot tub, and beachside gazebos. Indoors, the villa is a haven of comfort and style, from the cozy living areas to a fully-equipped kitchen, all designed to facilitate warm gatherings and memorable meals. As an added perk, guests enjoy special reduced rates for local activities, including beach rentals, golf, and tennis, as well as proximity to Miramar Beach's bustling restaurants, shops, and bars. Choose "Paradise Villa" for your fall break and elevate your Destin vacation experience to the realm of the extraordinary.

Treasure Chest

Treasure Chest Destin

4 Bedrooms / 3 Full Bathrooms / 14 Guests

For a fall break that captures the essence of coastal living without the crowds of a high-rise resort, consider Treasure Chest, a Mediterranean-style villa located in the serene Norwood beach-side community. This intimate Destin rental retreat accommodates up to fourteen guests across its four ample bedrooms, making it an ideal choice for families or groups of friends seeking an autumn oasis. The home's most striking feature is its private lagoon-shaped swimming pool, situated in a lush tropical landscape dotted with towering palm trees. Complement your sun-soaked afternoons with a visit to the adjacent Tiki Bar, which features a flat-screen TV and a gas grill, perfect for poolside meals and entertainment. Despite its secluded ambiance, "Treasure Chest" is conveniently situated just a short distance from the brilliant beaches of the Emerald Coast. Here, you can enjoy the natural beauty of the gulf without sacrificing the luxuries and amenities you'd expect from a high-end vacation rental. Choose "Treasure Chest" this fall and unlock the secret to a truly memorable holiday escape.

Townhomes at Crystal Beach 1

Townhomes at Crystal Beach

4 Bedrooms / 4 Full Bathrooms / 13 Guests

For a beachfront slice of paradise, explore one of the newest additions to our portfolio: Townhomes at Crystal Beach 1.This stunning four-bedroom, gulf-front townhome, perched across three levels, comfortably accommodates up to twelve guests. As an "end unit," it affords extra privacy, supplemented by an abundance of natural light from additional windows. The property boasts two spacious living areas perfect for unwinding, as well as a lower-level veranda that seamlessly connects to a beachfront sun deck. Two more verandas on the upper levels provide unrivaled views of the glittering Gulf waters, ideal for those autumn sunsets. If you prefer poolside leisure, the community offers a large, seasonally heated 32' x 15' swimming pool. Located in Destin's sought-after Crystal Beach neighborhood, this gem is just a stone's throw from Destin Commons, an idyllic retail village featuring Mediterranean architecture, royal palm-lined avenues, a diverse array of shopping options, casual bars, restaurants, and even an AMC Multiplex Theater. With its balance of seclusion and proximity to local attractions, "Townhomes at Crystal Beach 1" is your go-to destination for an exceptional fall break.

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Destin Fall Condo

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.

Aqua Sound

Aqua Sound Destin

4 Bedrooms / 3 Full & 1 Half Bathrooms / 11 Guests

For those seeking a blend of luxury and natural beauty this fall, Aqua Sound presents an unbeatable choice. This stately, four-bedroom, gulf-front vacation home accommodates up to eleven lucky guests. It is located in the prestigious residential area of Destin Pointe at the westernmost tip of Holiday Isle. The home boasts three levels, each offering expansive verandas; one side faces the breathtaking Gulf, and the other overlooks a serene coastal dune lake. The community features two large swimming pools, a hot tub perfect for cooler autumn evenings, tennis and shuffleboard courts, and a children's playground. When you're ready for adventure, you're just minutes away from HarborWalk Village, where dockside restaurants and bars with live music await. Enjoy special Ocean Reef Resorts guest discounts on a variety of local activities, from charter fishing trips and sunset dinner cruises to dolphin sightseeing and treasure hunts on pirate ships. Whether you're in the mood for outdoor activities or simply soaking up the scenic views, "Aqua Sound" offers a perfect autumn escape for families and friends alike.

Endless Summer

Endless Summer Destin

4 Bedrooms / 4 Full Bathrooms / 10 Guests

For an unforgettable Destin fall break experience, consider booking Endless Summer, a sprawling four-bedroom residence that comfortably accommodates up to ten guests—all in beds. Nestled in the gated oasis of Emerald Waters Village, this home grants beach access to its residents, just a stroll away. The centerpiece of this property is a stunning courtyard featuring a 29' x 14' swimming pool adorned with a decorative wall, complete with lion heads that spout water into the pool. To complement your autumn evenings, the tastefully furnished veranda comes equipped with an outdoor kitchen, wet bar, mini-refrigerator, and flat-screen TV for poolside entertainment. If you ever tire of your private paradise, two large community swimming pools offer additional recreation options. With both luxurious amenities and easy beach access, "Endless Summer" embodies the perfect setting for a relaxing and enjoyable fall getaway.

Sea Sail

Sea Sail Destin

3 Bedrooms / 3 Full & 1 Half Bathrooms / 9 Guests

Discover the ideal Fall Break haven at Sea Sail, a captivating three-bedroom beachfront Destin cottage that comfortably accommodates up to nine guests—all in freshly renovated, elegantly appointed spaces. Take advantage of the autumn sunsets with your own private beach, easily accessible via stairs from a first-floor sun deck boasting stunning views of the jewel-toned Gulf. The cooler evenings are perfect for stargazing from the shared balcony of the two gulf-front primary bedrooms, each complete with its own en-suite bath. For those looking for a unique retreat, the top-floor loft bedroom offers a cozy sanctuary. Featuring a vaulted ceiling, an arched palladium window, and an en-suite bath, this loft provides panoramic gulf vistas that are particularly breathtaking in the softer autumn light. Whether you're seeking outdoor adventures or intimate indoor gatherings, "Sea Sail" promises a Destin Fall Break filled with blessed moments and unparalleled comfort.


Snowdrift Destin

3 Bedrooms / 2 Full Bathrooms / 8 Guests

Plan a memorable Fall Break at Snowdrift, a three-bedroom gulf-front Miramar Beach vacation oasis that places you right on a snowy white sand dune, offering unparalleled proximity to the shore. With sleeping arrangements for eight delighted guests, this home is perfect for enjoying the seasonal tranquility of the coast. Take in awe-inspiring views from the Gulf-front balcony, furnished with upfront seating that lets you fully appreciate the sea's grandeur. Or opt for a fresh seafood meal on the side deck, where autumn breezes make for an idyllic dining setting. The interior is equally impressive, featuring a bright, vaulted open living area with a wall of sliding glass doors that not only lead to the beachfront balcony but also frame a sensational seascape. As the sun sets earlier in the fall months, enjoy the soothing sounds of the surf as you bask in the golden hour glow, making "Snowdrift" the ultimate Fall Break getaway.

Ocean Reef Fall Break Guests

Discover your perfect Fall Break destination among these ten 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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