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!

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.

Millstone on the Millpond-6 miles of Springs

This 3 bedroom, 3.5 bath house is so cozy you will feel right at home! It located in a well developed sub-division with approximately 125 feet from the water. This Millpond home is over the top with mid-century modern decor inside! Millstone has large windows that overlook the water and dock. This house is perfect for a family vacation, fishing trip, or a weekend getaway. Millstone is fully stocked and equipped with all the modern amenities you may need. Home comes with 4 Smart TV’s with WiFi!

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

“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.

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 and bar stools, couch, loveseat and rocker. Washer and dryer provided. No pets

The R & R Lake House on Lake Seminole

Fish, Hunt, Grill, or Chill with direct access to the big lake in just 8 minutes by boat.. Lake Seminole contains 37,500 acres of water, and a shoreline of 376 miles. Bass-Masters annual event attracts anglers from all 50 states. The fish include largemouth bass, crappie, chain pickerel, catfish, striped bass and others. Home is nicely decorated with a lake theme. Awesome Sunsets and views of the lake from the screened-in porch, backyard, 80ft dock, and boat house.

Cozy | Cabin close to Florida Caverns!

Cozy Retreat | Cabin Getaway🌲 Unplug and relax at this peaceful cabin surrounded by nature. Enjoy outdoor scenary, outdoor games, and grilling under the stars. Great for couples, solo travelers, or families—camper on-site available for extra guests. A perfect escape to recharge and reconnect. For a group bigger than four ask about our group option available.

The Cottage! 5 star! Hottub•fishing•dock/lift

Cozy cottage located on Lake Seminole known for it’s Award winning bass fishing! Open floor plan with light and airy colors throughout! Large screen porch overlooking Lake Seminole! Home is less than 50 feet from the shoreline. The lake is visible from almost every room in the home! Come and enjoy the peace and tranquility of Lake Seminole!