Vacation rentals in Chipley

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Top-rated vacation rentals in Chipley

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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

5 out of 5 average rating, 139 reviews

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

Guest favorite

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

4.91 out of 5 average rating, 45 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 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.

Guesthouse in Chipley

4.95 out of 5 average rating, 371 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 favorite

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, 171 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 favorite

Apartment in Ponce de Leon

4.92 out of 5 average rating, 172 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 favorite

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, 18 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 favorite

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, 109 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 favorite

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

4.85 out of 5 average rating, 26 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.

Top guest favorite

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, 209 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 favorite

A cozy living area showcases a brown sofa, positioned near a light-colored area rug. New kitchen appliances are visible in the background, with ample natural light streaming through a nearby window. A staircase leads to the loft, providing additional sleeping space.

Tiny home in Slocomb

4.97 out of 5 average rating, 152 reviews

Comfortable Tiny House In Wicksburg

Comfortable tiny home in Wicksburg, Alabama offers a loft with a queen size bed. The downstairs has another sleeping area that includes a twin size sleeper sofa. The kitchen is spacious enough to make your favorite meal. There is a scenic view for a peaceful stay, but only about 1 hours drive from places like Panama City Beach Florida. Also, Dothan is 14 miles and Ft Novosol is 12 miles away. We also offer high speed Internet and free, unlimited wifi.

Top guest favorite

A wooden porch swing is suspended from a support beam, positioned to overlook an open field. A vibrant sunset fills the horizon, blending soft hues of pink and orange against a backdrop of trees. The tranquil landscape invites moments of relaxation.

Tiny home in Ashford

4.95 out of 5 average rating, 105 reviews

Barndo“mini”um

Peaceful, private country retreat with beautiful views and friendly cows in the backyard. Enjoy your morning coffee on the porch swing and relax in the ultra-comfy bed after a quiet, restful night. Includes full-sized fridge, microwave, toaster oven, TV, Wi-Fi, and full bathroom. Just 10 minutes from Farley Nuclear Plant and 13 minutes from Southeast Health. Perfect for relaxing stays or quiet work trips. Come enjoy our little slice of paradise!

Superhost

An indoor pool is centered in a spacious room with bright blue walls and large windows, allowing natural light to fill the space. Comfortable seating areas are visible on either side, creating a welcoming setting for relaxation or entertainment.

Guesthouse in Chipley

4.91 out of 5 average rating, 23 reviews

Peaceful Romantic Escape, Pool, Spa, breakfast

Come and enjoy this beautiful, cozy, and tranquil getaway. Suite has 1 queen bed, kitchenette, bathroom with shower, smart tv. So many things to do on the property like enjoy the indoor pool, outdoor hot tub, goldfish pond with sitting area, chicken coop and vegetable garden , outdoor swing, outdoor movie nights, breakfast, and cottage bakery on property. All situated on a beautiful and peaceful country estate. Come and enjoy yourselves!