Family-friendly holiday rentals in Jackson County

Fielder's Choice - 1940s Brick Home Full of Fun

Have fun with the whole family in this stylish place conveniently located near Downtown, Chipola College, and the M.E.R.E (travel ball families-complex 4.5 miles). Fielder’s Choice, a 1940s brick home, is a perfect mix of new and old and packed with fun and games inside and outside! Jackson County’s ecotourism is thriving; 9 bodies of water for fishing, paddling, and tubing; adventure trails-walking and horseback; and Caverns. Explore new flavors in locally curated ice cream & craft beers. Pets!

A Taste of Farm Life

Have fun with the whole family at this stylish place. Our two-bedroom two bath home located in the country, surrounded by farm fields, barns and cow pasture. Great for vacations! Just an hour from the World's most beautiful beaches, 6 miles south of Graceville, FL, and 7 miles north of Chipley, Fl. There are two queen beds, and a pack-n-play. There is a highchair, children's table and chairs, dining table, bar, bar stools, couch, and loveseat. Washer and dryer provided. No pets or smoking.

Guesthouse & Pool

This family friendly home is less than 2 miles from Walmart and restaurants. Wifi, Netflix, Starz, Prime video are included with your stay. There is one queen bed, one full bed, a queen size sleeper sofa, & a twin. All of which can accommodate a total of 7 guests. Chipley is located off I-10. It is a 55-minute drive to the beach and a 45-minute drive to Dothan, AL. Falling Waters State Park is 3 miles away. Caverns park 15 miles. No pets & no smoking allowed. Home is sanitized between guests.

Peaceful & Beautiful Lake Cabin, Boat House/Dock

Located on beautiful Lake Seminole, a short distance from the hosts main house. Includes use of boat house & dock (you'll need your own boat). 2 boat landings within a mile. Across the lake from Lake Seminole State Park. Within 2 miles of gas station, Dollar General & restaurant. 45min to FL ST Caverns. Free wifi. Full Kitchen is equipped with dishes, pots pans, full size oven/range, refrigerator, microwave, coffee maker. Large flat screen TV, screened in porch and back deck near fire pit

Merritt's Mill Pond Hideaway

Escape to our peaceful Merritt's Mill Pond Hideaway! Nestled on 2.5 private acres with 300ft of gorgeous waterfront, this rural retreat offers a balance of nature and comfort. Swim, kayak, or snorkel from your dock. Watch wildlife from deer to eagles, then marvel at starry skies so clear you'll spot the Milky Way. Just minutes from Florida Caverns State Park and a short drive to Jackson Blue Springs. A true North Florida gem where family meals and nature's soundtrack create memories that last.

“The Q'whack Shack" on Lake Seminole with Dock

Aptly named, “The Q'Whack Shack,” our quaint lakefront home is the perfect host accommodation for a charming weekend or weeklong reprieve. Ideally situated on the heart of Lake Seminole, The Q’Whack Shack is a water enthusiasts dream hideaway. Enjoy boating, angling, an array of watersports (skiing, tubing, etc.), grade-A bass fishing and duck hunting with convenient private dock access just steps from the back door. Waterfront restaurants and other provisions just a quick boat/car ride away.

Cozy Barndominium

This quaint barndo leaves nothing to be desired with its charming, rustic interior and modern amenities. New appliances and all the comforts of home are sure to make your stay as pleasant as possible. This is a 1 bedroom 1 bathroom home with two additional twin beds in the loft. This is a smaller space but is very functional and comfortable. Only 50 minutes from Panama City's white sand beaches and 7 minutes from Chipley, it's conveniently located for those wanting to explore.

LouLouBell's Getaway

This unique place has a style all its own. A quiet getaway only 1 mile from Lake Seminole. We have space to park your boat in the grass. Goats on the property for petting, or feeding cheerios. Firepit and swings at night. It is a close drive to Alabama, Georgia, or the Panama City Beaches. Historic Marianna is only 20 minutes away with caverns, tubing, and shopping. Sneads has immediate amenities including groceries, gas, and restaurants, and is only 1 mile from BNB.

The Tiny House of Healing - Rustic Rural Edition

Let the honeybees restore what the locusts have taken! Peaceful ranch-style cottage with loft, full kitchen and bath. King bed on main level, queen in loft, plus recliner. Enjoy a swingset, tree swing, board games, and walking trail. Bring the kids and enjoy the outdoors! Located between many springs and caverns. Fresh, crisp well water straight from the tap believe to be the same water that flows into the springs! Come rest, recharge, and breathe deep.

Windmill Way

A cozy remodeled farmhouse in a quiet rural country setting, but only 2 miles to town. It's surrounded by open fields, barns, cows and windmills. Enjoy the fresh air, nature and the wind blowing through your hair. Windmill Way is inviting with farmhouse decor, soft lighting, comfortable furniture and new appliances to make the space feel like a true home. It's the kind of place where you can just relax, read a book or sit on the porch and enjoy the view.

Chipola Woods quiet & cozy near Caverns, Bear Paw

No cleaning fees! Our one & only peaceful, quiet golf cart friendly location conveniently between I-10/US90 yet the Caverns, Bear Paw river float, Merritts Mill Pond, Hinson Nature Preserve, Blue Springs and all shops, cinema, boat launches & restaurants within a 10 min drive. Golfing, beach, & airports within 1 hour. Modern cottage on a private 1/2 acre equipped with large smart TV's in both the living room and bedroom with Prime video.

Cabin close to FL Caverns Hot Tub, WI-FI & Firepit

Handcrafted, owner-built cabin in a peaceful rural setting near Marianna, Cottondale, and Chipley. Ideal for guests who enjoy nature-forward stays rather than hotel-style luxury. Relax in the private hot tub, gather around the outdoor fire area, and explore Florida Caverns State Park just 14 minutes away. Located near Hwy 90, guests may occasionally hear light road noise consistent with a rural highway setting.