Holiday houses in Chipley

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Top-rated holiday rentals in Chipley

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

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Top Guest favourite
A wooden deck is surrounded by tall trees, providing a natural backdrop. A small round table is set with a few plant pots and decorative items. Metal chairs are positioned around the table, inviting moments of relaxation in a serene outdoor setting.
Home in Graceville
4.91 out of 5 average rating, 90 reviews

Cozy & quiet House in the country

Relax with the whole family at this peaceful place. Please note there is NO WI-FI at this location. Feel free to Bring your dog and enjoy a fenced in back yard. We are happy to assist with directions and recommendations! •2 miles from the silos wedding venue . • 14 miles from Falling waters state park ( biggest waterfall in FL) • 29 miles from Florida caverns state park • 33 miles from Ponce de Leon State park • 38 miles from Econfina Creek ( Natural Springs ) • 27miles from Cypress Springs

Guest favourite
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
4.89 out of 5 average rating, 47 reviews

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.

Guest favourite
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
4.95 out of 5 average rating, 377 reviews

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.

Guest favourite
The exterior of a single-story remodeled home is shown, with a light-colored facade and dark shutters. A welcoming front porch is visible, framed by a spacious lawn surrounded by trees, offering a peaceful rural setting.
Home in Vernon
4.91 out of 5 average rating, 176 reviews

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

Guest favourite
Apartment in Ponce de Leon
4.92 out of 5 average rating, 175 reviews

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.

Guest favourite
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
4.89 out of 5 average rating, 19 reviews

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!

Top Guest favourite
A welcoming porch is featured at the front of a single-story house, flanked by tall trees and lush greenery. The home has a sloped metal roof and is set against a serene natural backdrop, creating a peaceful atmosphere.
Cottage in DeFuniak Springs
4.89 out of 5 average rating, 114 reviews

Beautiful cottage nestled in the country

Relax with the whole family at this peaceful and serene place to stay. Surrounded by mature trees and beautiful foliage. Quiet and majestic, spend the days at the beach or springs and the nights listening to nature as you star gaze away from the bright lights of the city. Take a nice nature walk down the trails or relax reading a book. A country escape to recharge and just a few miles from town and close to the beach, so you can have the best of both worlds. Your little piece of heaven awaits!

Guest favourite
A spacious kitchen area features a large wooden island with seating for three. Modern appliances, including a refrigerator and microwave, are visible against white cabinetry. The high ceiling is enhanced by a gentle fan, and natural light streams in from the nearby door and window.
Barn in Chipley
4.86 out of 5 average rating, 28 reviews

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.

Guest favourite
A spacious living area features a large sectional couch in muted tones, complemented by a rustic wooden coffee table. Large windows allow natural light to fill the room, while a flat-screen television is positioned on a light-colored media console. The entrance door opens to the outside.
Home in Chipley
4.97 out of 5 average rating, 66 reviews

Peaceful Pines

This country home sits on 5 acres with 2 spring fed ponds. Enjoy the great outdoors under the pavilion with picnic tables, a porch swing & grill. There are cards, games & puzzles available for some screen-free time. Since we’re away from the city lights, the night sky is absolutely breathtaking. If you’re looking for privacy and quietness, this is the place to be. * Simple check-out instructions. We just ask that you run the dishwasher & put your trash in the bin.

Top Guest favourite
A wooden swing is suspended from a sturdy tree branch, overlooking a peaceful pond surrounded by lush greenery. The water reflects the clear blue sky, and the distant tree line creates a serene backdrop, inviting relaxation and contemplation.
Cottage in Dothan
4.99 out of 5 average rating, 210 reviews

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.

Guest favourite
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, 7 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.

Guest favourite
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.
Home in Marianna
4.89 out of 5 average rating, 28 reviews

Cabin close to FL Caverns! Pool, WI-FI, & Firepit

Cozy Retreat | Cabin Getaway🌲 Unplug and relax at this peaceful cabin surrounded by nature. Enjoy outdoor scenary, outdoor games, and having a Fire under the stars. Great for couples, solo travelers, or families—camper on-site available for extra guests. A perfect escape to recharge and reconnect. And conventionally located just 14 minutes from the Florida Caverns State Park! For a group bigger than four ask about our group option available.

Popular amenities for Chipley holiday rentals

Quick stats about holiday rentals in Chipley

  • Nightly prices starting at

    Chipley holiday rentals start at $87 NZD per night before taxes and fees

  • Verified guest reviews

    Over 380 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Chipley rentals

  • 5 Average rating

    Chipley stays are highly rated by guests—averaging 5 out of 5!

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