Vacation rentals in Jackson County

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Top-rated vacation rentals in Jackson County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

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.

Home in Marianna

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!

FamilyValueKitchen

4.83 out of 5 average rating, 117 reviews

Top guest favorite

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

LocationValueOutdoor spaces

4.94 out of 5 average rating, 81 reviews

Top guest favorite

Home in Grand Ridge

Mimi's Cottage Cozy King bed, near tournaments!

Conveniently located 6 minutes off I-10. Away from it all, yet close enough to Marianna to grab a bite or make it for tournaments and early games. Visiting to take in all Jackson County has to offer? We are 8 minutes from your boat being launched in Lake Seminole or 10 minutes from the Apalachicola River. *45 min. to Dothan, AL *1 hr. to Tallahassee *1hr 15min. from the World's Most Beautiful Beaches We'd love to host your family! No refunds on cancellations within 24 hrs of reservation time.

FamilyLocationCondition

4.98 out of 5 average rating, 51 reviews

Top guest favorite

A patio set with two chairs and a small table is positioned on a wooden dock overlooking Lake Seminole. The serene water reflects a gradient of soft colors at sunset, creating a calm atmosphere. Surrounding trees are visible along the shoreline.

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

LocationValueTV

5.0 out of 5 average rating, 169 reviews

Top guest favorite

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.

Home in Marianna

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.

LocationValueTV

4.97 out of 5 average rating, 38 reviews

Guest favorite

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.

FamilyValueHospitality

4.88 out of 5 average rating, 233 reviews

Top guest favorite

A charming outdoor porch features two wicker chairs adorned with decorative pillows, positioned around a small blue table. The backdrop displays a vast green field under a clear sky, with trees lining the horizon, creating a peaceful rural setting.

Home in Graceville

The Rodeo Inn

Relax with the whole family at this peaceful place to stay. The Rodeo Inn features all things rodeo and country. Nestled near the heart of Graceville and just 30 mins south of Dothan, AL, you are surrounded by a lot of farmland. Wake up to birds chirping and watch beautiful sunsets off the front porch at night. Tons of antique shops near by, as well as natural springs in every direction including The FL state Caverns (underground caves). If you need some quiet time & relaxation, this is it.

LocationValueDecor

4.93 out of 5 average rating, 102 reviews

Top guest favorite

Cabin in Donalsonville

Lakefront Serenity Cove

Whether you are here for a respite, competing in a fishing tournament or a snowbird looking for a restful place to spend the winter, Serenity Cove has much to offer to all types of travelers. Just 3 minutes to many boat landings out to Lake Seminole! Ample parking for multiple cars and trucks with trailers. The nearby riverfront town of Bainbridge (20 min) has a lovely town square with a vibrant restaurant, shopping and art scene. NOTE: FISHING from Serenity Cove is from the DOCK ONLY.

LocationFamilyCondition

5.0 out of 5 average rating, 34 reviews

Guest favorite

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.

Apartment in Chipley

Guesthouse & Pool

This family friendly apartment is one half of a duplex. It is less than 2 miles from Walmart & restaurants. Wifi, Netflix, & Prime video, are available, as well as over 400 commercial free movies & tv shows on Fandango. There are 2 queen beds & 1 full bed. Chipley is located off I-10. It is a 55-minute drive to the beach & 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.

FamilyValueCheckout

4.95 out of 5 average rating, 484 reviews

Top guest favorite

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

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.

LocationFamilyAccuracy

4.97 out of 5 average rating, 29 reviews

Top guest favorite

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 private 1/2 acre equipped with large smart TV's in both the living room and bedroom with Prime video.

FamilyLocationQuiet

5.0 out of 5 average rating, 178 reviews

Guest favorite

The spacious exterior of the waterfront retreat is presented, featuring a white wooden façade with a covered porch supported by columns. Green shrubs and trees surround the property, and a broad lawn stretches out under a bright blue sky, providing a sense of openness.

Home in Seminole County

Satterfield Boat House

Placid waterfront retreat with large dock. 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.

ValueFamilySleep quality

4.96 out of 5 average rating, 69 reviews