Holiday rentals with outdoor seating 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!

Guesthouse & Pool

This family friendly home is less than 2 miles from Walmart and restaurants. Wifi, Netflix, and Prime video are included with your stay. There is one queen bed, one full bed, a queen size sleeper sofa, and 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 and no smoking allowed. Home is sanitized between guest.

The Tiny House of Healing - Rustic Rural Edition

Let the honey bees restore what the locusts destroyed in your life! Take a step back in time, when there was no wifi, everyone had well water, gardens at everyone's house and God was held in reverence. Put the phone down and get to know each other again or finish writing that book in the quiet. Board games, a swing and walking trail provided. No wifi but usually 1-2 bars of service (so it is possible to use a mobile hotspot) Fully equipped kitchen. King bed, recliner and queen bed in loft

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.

Big Home with HotTub on Lake Seminole

Lakefront house has 4 Large Bedrooms & 2½ Baths. 10 people can comfortably sleep in this spacious 2250 square foot house. You will enjoy a massive fireplace, cathedral ceiling with cypress beams, and a large sun-room offering a wonderful view of the lake, two miles from Seminole State Park & a slip for boats nearby. The lake is perfect for all boating activities including fishing, skiing, and pulling kids on tubes. Pets are welcome. There is a $100 pet fee. Hot tub will be filled and ready!

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.

The Willis House

Come forget about your worries at this peaceful 6 acre historic property built in 1917. The huge oak trees surround this property making it a built in canopy. This keeps the house cooler in the summer. Sit or walk around the 4500 square feet of porches and catch a breeze or sit and have quite time. The home has been recently remodeled and set to current fire code standards. The house has a lot of room to roam full upstairs and downstairs.

Satterfield Boat House

Placid waterfront retreat. Great for observing wildlife and enjoying the peaceful outdoors, away from the hustle and bustle of urban and suburban areas. A wonderful location for fishing in the spring and summer, duck hunting in winter, and boating year-round. Enjoy the temperate weather in the fall and spring. Nearby spots to visit include local lakeside restaurants and wildlife parks.