Vacation rentals in Jackson County

5 out of 5 average rating, 139 reviews

A wooden gazebo is set in a lush green setting, featuring a small table with two chairs. The open structure showcases decorative railing and is surrounded by trees, creating a peaceful outdoor seating area.

Cottage in Marianna

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 1/2 acre equipped with large smart TV's in both the living room and bedroom with Prime video. Queen pullout sofa w/mattress topper for extra comfort *on request

Superhost

A serene bedroom is showcased featuring a spacious bed with a textured blue coverlet and a decorative striped pillow. A barn door leads to a modern bathroom, while a white brick fireplace adds character. Natural light filters through patterned curtains, enhancing the calming atmosphere.

4.81 out of 5 average rating, 79 reviews

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!

4.95 out of 5 average rating, 367 reviews

An outdoor pool area is enclosed by a white fence, featuring a large blue swimming pool complemented by a spa. Comfortable lounge chairs are arranged around the deck, and a gazebo provides shaded seating. Tall trees and clear blue skies create a serene backdrop.

Guesthouse in Chipley

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.

A bright living area features two brown leather sofas facing a wooden coffee table. A large flat-screen TV is mounted on the wall, with natural light flowing through sliding glass doors that lead to an outdoor deck surrounded by trees.

4.99 out of 5 average rating, 83 reviews

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!

4.88 out of 5 average rating, 16 reviews

A cozy sleeping area features a spacious bed dressed in white bedding, complemented by a decorative pillow that reads 'Happy.' Natural light enters from a skylight above. Two small nightstands provide storage, and decorative flowers are placed on one of them.

Farm stay in Graceville

Let’s Camp - Florida Edition!

Come to a place of grace in Graceville! Enjoy nature and the drink the well water that taps into the natural spring reservoir! We have 5 acres for you to explore with a trail into a majestic forest! Plenty of space for kids to run in a safe location! We are in a central location to Ponce De Leon Springs, Morrison Springs, Florida Cavern State Park and so much more! No pet fee for pets staying outside. Too rural for WiFi, so you can get off your devices and enjoy each other! Happy camping!

5 out of 5 average rating, 151 reviews

A welcoming entrance features a screened porch with a decorative door. Surrounding greenery includes trimmed bushes and a tree. The grassy lawn extends beyond, with additional trees in the background, creating a serene atmosphere.

Home in Donalsonville

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

A hot tub is set on a patio, with water illuminated in soft blue tones. Surrounded by a lush green lawn, it overlooks a serene pond and tall trees. A wooden deck is visible in the background alongside a grill, emphasizing outdoor leisure.

4.9 out of 5 average rating, 10 reviews

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.

4.88 out of 5 average rating, 213 reviews

A relaxing outdoor space features four blue chairs arranged around a fire pit, set against a scenic lakeside view. The backdrop showcases a tranquil lake at sunset, with reflections of vibrant orange and purple hues in the water. Tall trees frame the area, enhancing the peaceful atmosphere.

Home in Donalsonville

“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.

4.93 out of 5 average rating, 43 reviews

A spacious single-story home is shown, featuring a gray exterior with white trim. The front porch is accessible by steps, and large windows allow natural light to fill the interior. Lush green grass and young trees surround the property.

Home in Graceville

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

4.95 out of 5 average rating, 184 reviews

The lakefront house features a charming red exterior with white trim and circular windows. Lush greenery envelops the entrance, where soft lighting highlights the welcoming atmosphere. The roof is peaked, and the front path leads to the doorway, framed by well-maintained landscaping.

Home in Donalsonville

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!

Superhost

A charming farmhouse exterior is presented, featuring a white facade and a green metal roof. Two rocking chairs are positioned on the porch, complemented by decorative elements. Lush green grass surrounds the home, offering a serene rural view against the backdrop of open fields.

Home in Graceville

5 out of 5 average rating, 3 reviews

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 exterior of the cozy cabin is presented, featuring a welcoming porch with seating. A wooden door is framed by large windows, allowing natural light to flood the interior. The surrounding landscape consists of trees and a gravel pathway leading to the entrance.