Fall in Northeast Florida is a hidden gem. With crisp evenings, golden sunsets, and the sound of the river lapping at the shore, our properties offer a front-row seat to nature’s most beautiful season. With homes minutes from the Jacksonville Jaguars home stadium, Ever Bank, plenty of heated pool homes, hot tubs and fire pits, Joseph Ellen has your fall stay covered.
🍁 Top Fall Rentals in Jacksonville
Tucked away in the peaceful riverfront neighborhood of Monterey, Bluff Haus brings treehouse-inspired living to life along the banks of the St. Johns River. Thoughtfully designed for families, friends, or couples seeking a serene getaway, this 3BR/2BA retreat blends organic textures, open spaces, and modern comfort in perfect harmony.
Wake up to sweeping water views and the soft sound of nature. Enjoy slow mornings with coffee on the deck, followed by a rejuvenating session in the private sauna. Inside, the airy living space invites connection—with a fully equipped kitchen, dining area, and cozy gathering spaces that make every meal and moment feel special.
As evening falls, step outside to watch the sunset reflect off the river—an effortless reminder of why Florida’s fall season is so magical. Whether you’re planning a quiet weekend retreat or a stay close to downtown Jacksonville, Bluff Haus is your place to unwind, reconnect, and soak up the beauty of the Northeast Florida waterfront.
Just 4 minutes from EverBank Stadium, The Bold City Retreat offers the perfect blend of local charm and modern comfort. Set in Jacksonville’s historic Springfield neighborhood, this stylish duplex features two private 3BR/2BA units—ideal for groups, families, or friends who want to stay close to the action while enjoying plenty of space to unwind.
Start your mornings with coffee from a neighborhood café, stroll past colorful murals, or explore Springfield’s lively brewery scene. Each unit is thoughtfully designed with cozy living areas, fully equipped kitchens, and inviting bedrooms—creating a stay that feels like home with an urban twist.
After a day downtown or cheering on the Jags, return to your retreat and relax in comfort. Whether you’re here for game day, a weekend getaway, or a long-term stay in Jacksonville’s most vibrant district, The Bold City Retreat is your front-row seat to everything the Bold City has to offer.
Bring on sweater weather — Florida style. Heated Poolside Oasis is a private Jacksonville retreat designed for easy relaxation and year-round enjoyment. With a sparkling heated pool and a firepit perfect for crisp fall evenings, this home strikes the perfect balance between comfort and fun.
Inside, you’ll find bright, welcoming spaces made for gathering — a fully equipped kitchen, open living area, and cozy bedrooms ideal for families or small groups. Outside, unwind by the pool as the sun sets, or roast marshmallows under the stars while the air cools.
Just a short drive from Jacksonville’s beaches and downtown, Heated Poolside Oasis offers that ideal fall blend of sunny days, cool nights, and endless ways to relax.
Cooler days and cozy nights find their perfect match at Sea Grape Villa, a bright, welcoming retreat tucked in a quiet Jacksonville neighborhood. Designed for togetherness and relaxation, this stylish home blends laid-back coastal living with all the right touches for a fall escape.
Spend your afternoons lounging by the pool or challenging friends to a round of ping-pong, then wind down as the sun sets in the heated pool — your own private spot to soak, unwind, and savor the season. As night falls, gather around the firepit for stories, laughter, and a little stargazing under Florida’s soft autumn skies.
Inside, open living spaces, a fully equipped kitchen, and comfy bedrooms make this home feel effortlessly inviting. Whether it’s a weekend getaway or an extended stay, Sea Grape Villa is a warm, easygoing escape made for fall memories that linger.
Nestled right on Julington Creek and the tranquil St. Johns River, Waterfront Paradise is the ultimate choice for creating effortless fall memories in Northeast Florida. This sprawling, 7-bedroom retreat offers room for up to 20 guests, making it ideal for family reunions, group vacations, or friends’ weekends where everyone wants to stay together and enjoy the season in style.
By day, cast off from your private dock for a boating adventure, fish straight from the yard, or relax on the sunny deck with a good book. Gather by the pool for cooled-off afternoons, or fire up the propane grill and enjoy dining al fresco while watching the boat lights dance across the water as evening falls. Come night, the hot tub is the perfect place to unwind under autumn’s starlit skies. Westerly breezes bring cool, comfortable evenings — ideal for lingering around the fire pit with friends over drinks and stories.
Inside the home, soft lighting, cozy gathering spaces, fully equipped kitchens, and all-season comforts make it easy to settle in after a day of exploration or water adventures. Nestled between nature and convenience, Waterfront Paradise delivers a true seasonal escape — where long afternoon sails, casual riverfront dinners, and nights around the fire pair perfectly with cooler air and fall charm.
🍂Top Fall Stays in Saint Augustine
1. Octopus Cove
Perched in St. Augustine’s Uptown district, Octopus Cove is a chic waterfront retreat made for crisp coastal mornings and golden-hour views. This industrial-modern escape blends sleek design with cozy comfort — perfect for a fall weekend getaway or a longer coastal stay.
Sip your morning coffee while watching the sunrise over the water, then spend the day wandering Uptown’s eclectic mix of boutiques, coffee shops, and art galleries. As the evening cools, return to your private patio to take in panoramic water views — the perfect backdrop for a glass of wine and night in the hot tub or around the fire.
From its stylish interiors to its unbeatable location just minutes from historic downtown, Octopus Cove offers a fall stay where modern design meets St. Augustine charm.
Just minutes from historic downtown St. Augustine, Cruiser’s Cove is the ultimate fall retreat for travelers who love a blend of local flavor and laid-back comfort. Set in the vibrant West King district, this newly updated 4-bedroom home puts you steps from some of the city’s best breweries, cafés, and restaurants — perfect for crisp afternoons and cozy evenings out.
Spend your mornings exploring cobblestone streets and local markets, then come home to unwind around the fire pit, enjoy the hot tub or gather for football and dinner on the patio under soft fall skies. Inside, you’ll find bright, modern spaces designed for connection — whether you’re cooking in the fully equipped kitchen or relaxing in the spacious living area after a day downtown.
With ample parking for cars, RVs, or even a boat trailer, Cruiser’s Cove is made for easygoing group getaways. Enjoy the best of St. Augustine’s fall season — from cool coastal breezes to warm local charm — all from a home that puts you right in the heart of it all.
Fall in St. Augustine is a season for slowing down, and Arpieka Garden is the perfect sanctuary to enjoy it. Nestled on Anastasia Island, this 5-bedroom, 3-bath home feels like a tropical retreat — but it’s only about a five-minute walk from downtown’s historic streets, charming cafés, and charming waterfront views.
From the moment you arrive, you’ll discover thoughtful design touches that make this home feel like a celebration of fall living. French doors invite breezes into the airy living space, while a lush private courtyard beckons you to relax with friends and family around the hot tub, tiki-lit seating area, and fire pit. Inside, modern furnishings, open living areas, and a gourmet kitchen create a welcoming space where laughter and conversation flow freely.
By day, explore iconic nearby landmarks like the St. Augustine Lighthouse & Maritime Museum and Alligator Farm Zoological Park, or stroll to local shops and restaurants for an afternoon treat. By night, savor crisp Florida air under string lights as you gather for s’mores or outdoor movie nights.
Soak up the season at Pelican’s Nest, a bright and inviting beachside escape designed for fun and relaxation. With three bedrooms and plenty of space for the whole crew, it’s perfect for families or groups looking for a laid-back fall stay near the coast.
Take the golf cart out for a cruise to nearby beaches, or spend the day enjoying everything right at home — from outdoor games and ping pong to a dip in the pool or a soak in the hot tub. As the sun sets, gather around the fire pit or relax in one of the many outdoor seating areas for breezy evenings under the lights.
At Pelican’s Nest, fall means easy mornings, golden afternoons, and cozy nights made for connection.
Tucked in the charming South Lincolnville neighborhood, The Lincolnville Trio is a quintessential St. Augustine stay that feels both timeless and inviting. Just steps from the Historic District, this unique three-unit property includes two stylish 1BR/1BA apartments in the front duplex and a private 1BR/1BA cottage in the back — all yours to enjoy.
Spend cool fall mornings walking beneath the oak-lined streets toward Flagler College or a cozy local café. In the evenings, return home to relax on the porch or gather in one of the comfy living spaces for a quiet night in. Each unit is thoughtfully designed with plush beds, fully equipped kitchens, and the warm character that makes St. Augustine so special.
Perfect for families, couples, or groups who want space and connection, The Lincolnville Trio offers an authentic stay that blends local charm, walkability, and comfort — a true fall favorite in the Nation’s Oldest City.