Vacation rentals in Chipley

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

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.

Entire home with lakefront access

Looking for a tranquil getaway? Come relax in this beautifully remodeled lakeside home, set amidst the peaceful rural surroundings. Whether you enjoy canoeing, kayaking or fishing, the beautiful Hicks Lake awaits you. And if you're craving a day at the beach, Panama City Beach is just a short 45-minute drive away! But that's not all - you're also just minutes away from several breathtaking natural springs, including Cypress Springs, Vortex Springs, Wiliford Springs, and spring-fed Ecofina Creek

Luxury Country Stay | Pool, Spa, Art Studio, Bfst

Welcome to Camelot’s Serenity Suite, a spacious private retreat with 2 queen beds and a private entrance. Relax by the fire pit, enjoy the waterfall and pond, or unwind in the indoor pool & outdoor hot tub. Start your day with a delicious homemade breakfast of pancakes and farm fresh eggs. Get creative in the on-site art studio (fees apply). Need more space? Other suites are available. With elegance, comfort, and nature all around, this serene escape is the perfect place to relax and recharge!

Backyard Bungalow

Dip into adventure at the Backyard Bungalow — just minutes from three of Florida’s most stunning natural springs. Less than 5 minutes from Ponce de Leon Spring State park. Only 10 minutes to get to Vortex Springs or Morrison Springs. Drive 45 minutes to the beautiful white sand beaches in Panama City beach, or Grayton beach in Santa Rosa. Make yourself at home and rest and reset in a country atmosphere. We look forward to hosting you. PET FEE is $25 NO CLEANING FEE Airbnb is behind our home.

Cozy Cottage in the Pines

Enjoy a quiet stay just outside of town on a farm! Listen to the breeze whisper through the pines and relax in this peaceful country setting. The cottage is 2 miles north of Cottonwood and is just under 10 miles to The Ross Clark Circle in Dothan. Dothan has a lot to do…..shopping, dining, and entertainment. Also, the cottage is only a few miles from the Florida line and the Georgia line if you’re going there for something fun! WiFi is fast so working from the cottage is easy as well!

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.

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

Cozy Retreat | Cabin Getaway🌲 Unplug and unwind at this peaceful cabin retreat surrounded by nature. Soak in the relaxing hot tub, enjoy outdoor scenery, play games, and end the day gathered around a crackling fire under the stars. Perfect for couples, solo travelers, or families—plus, an on-site camper is available to accommodate extra guests. Conveniently located just 14 minutes from Florida Caverns State Park, this getaway is the ideal escape to recharge and reconnect.

Juju’s Pond House on Smith Pond

Take it easy at this unique and tranquil getaway located on 100 acres and nestled quietly on a private pond. The house was originally built in 1921 and in 2018 we had the house moved down to the pond and did a full renovation while preserving as much original character as we could. Enjoy your morning coffee and watch the sunrise from the screen porch swing or one of the docks at the pond. The property has nature trails to explore, fishing, and plenty of wildlife.

Shady Oaks Cabin on the Hill

Nestled in a serene country setting, this is our guest house up the hill from our country home. The Little White Cabin under the oaks is the perfect retreat for anyone seeking peace, charm, and simplicity. A newly painted facade in crisp white, the cabin’s mint-green door and cozy front porch complete with rocking chairs offer the ideal spot to sip your morning coffee or unwind at sunset. Close to local springs and a short 45 min drive to Panama City Beach.

Pace e Amore - Adorable 1 Bedroom Cottage

You will love this super cute and cozy cottage. All the amenities you will need to fully enjoy your stay. outdoor gazebo with fireplace, and more. Centrally located just minutes from the bay with boat launch, mini beach and picnic area. Plenty of restaurants and shopping nearby as well. Beautiful Panama City Beach is a mere 20 minutes away . Come and enjoy a fun and relaxing time as our guests at "Pace e Amore.