Holiday houses in Chipley

5 out of 5 average rating, 137 reviews

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

5 out of 5 average rating, 5 reviews

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!

4.91 out of 5 average rating, 32 reviews

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

Apartment in Ponce de Leon

4.93 out of 5 average rating, 152 reviews

Backyard Bungalow

Bring the whole family to this great place with lots of room to spread out. 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. This Airbnb is behind our home, where we live.

5 out of 5 average rating, 113 reviews

Townhouse in Dothan

Special Rates For Summer! Chadwick Townhouse

Experience the best of Dothan in this stylishly renovated townhome. Perfectly situated for adventure, you're just moments from championship golf at RJT and DCC, thrilling water fun at Water World, exciting games at the Westgate Baseball and Tennis Complex, the serene beauty of Forever Wild trails, and conveniently close to both area hospitals. Unwind in comfort with a fully equipped kitchen, perfect for whipping up delicious meals and stay connected with blazing-fast Wi-Fi.

4.99 out of 5 average rating, 194 reviews

Cottage in Dothan

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.

4.95 out of 5 average rating, 103 reviews

Condo in Long Beach

BeachFront - Ocean View -Majestic Beach Resort 809

Majestic Beach Resort Tower 1, Studio, 8th Floor! Welcome to your Gulf-Front paradise! With outdoor and indoor pools, hot tubs, and 650 ft. of shoreline! So much to enjoy, all within the resort! Starbucks, H2O Bar & Grill, Market & Gift Shop, a movie theater and so much more! This studio condo sleeps 3. King size bed with new memory foam mattress. Single rollaway cot bed. Smart TV, Wi-Fi, fully equipped kitchen, private balcony overlooking the Gulf of Mexico!

5 out of 5 average rating, 4 reviews

Guesthouse in Chipley

Romantic Country Escape Pool Hot Tub 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, 2 fire pits, 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!

5 out of 5 average rating, 22 reviews

Home in Chipley

Making Memories Lucas Lake

The sun seems to shine brighter on this lovely lakefront home! Ideal for family nature retreats. Enjoy boating, water sports, fishing and kayaking on this 480 acre spring fed lake with 2 boat landings and private dock. Relax on the large deck with dining, lounging and grilling areas; overlooking the spacious back yard with firepit and plenty of room for outdoor games and beautiful lake views.

4.94 out of 5 average rating, 124 reviews

Home in Marianna

"The Marianna"- Cute Cottage in Historic Downtown

Our cottage is centrally located in downtown Marianna. You will be walking distance to restaurants and shopping. The cottage is uniquely decorated and has all of the amenities you need. There is a large front porch and also a back yard area for enjoying your morning coffee or afternoon sunset. Smart TV's are in the living room and both bedrooms. The bedroom both have queen beds.

4.98 out of 5 average rating, 144 reviews

Tiny home in Slocomb

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 spacious kitchen has new appliances. 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.

4.99 out of 5 average rating, 126 reviews

Home in Altha

Wandering Waters Cabin

FISH-HUNT-BIKE-SWIM-KAYAK-GLAMP Come stay on the beautiful Chipola River in the Florida Panhandle. This inviting cabin overlooks the river with a spacious dock that can be used for a variety of water activities. The house is centrally located approximately one hour from Tallahassee, Dothan, and Panama City Beach-the World's Most Beautiful Beaches.

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Other great holiday rentals in Chipley

5 out of 5 average rating, 10 reviews

Tiny home in Marianna

The Big Bend Tiny Home

CarolinaRating, 5 stars2 months ago

The tiny home was amazing! Great decor, free of clutter and everything you need. Plenty of space and easy to find

4.73 out of 5 average rating, 112 reviews

Cottage in Bainbridge

Cozy, modern 2 bedroom, 2 bath cottage

CarrieRating, 5 stars3 weeks ago

Absolutely a great stay. We had everything we needed. The house was well stocked for a weekend stay. We loved the screened in patio even tho it was very hot out, there was always a nice breeze and no nats. The lake and the neighborhood were nice extras.

5 out of 5 average rating, 48 reviews

Home in Dothan

Daniel Digs - 3/2 In Super Location

JustinRating, 5 stars1 week ago

Our SECOND STAY at Daniel's Digs was just as pleasant as the first! When in Dothan, this will be our go-to AirBNB! Great hospitality and a really inviting house!

4.88 out of 5 average rating, 51 reviews

Cabin in Altha

Breathtaking Luxury Riverside Retreat. Sleeps 10.

UltraRating, 5 stars2 weeks ago

I took my kids to stay at Amber's place for my son's graduation celebration trip, ranging in age from 7-23 and we all had an amazing time, as our trip was drawing to an end we even added an extra night with no problem at all, the beds were very comfy, the water stayed very hot even between all of us taking showers the entire visit, we used the local boat ramp to bring our own boat and easily tied it off at the houses dock. Kitchen had everything we needed for our stay! The ice maker on the refrigerator did not work, and I'm not including that in this review as a negative. just an informative so you know to bring your own ice, it did not effect our trip in any way at all, we just got bagged ice! We enjoyed our time together here so much, I can not thank Amber enough for sharing her home with myself, my family and others to experience the beauty tucked away in Altha!

4.78 out of 5 average rating, 69 reviews

Home in Marianna

Fielder's Choice - 1940s Brick Home Full of Fun

ThomasRating, 5 stars1 week ago

Very nice home, nice kitchen, very nice relaxing back deck with hot tub, walkable to movie theater, restaurants.

4.95 out of 5 average rating, 38 reviews

Apartment in Panama City

Oasis by the Bay. 10 miles from Panama City Beach

MadilynRating, 5 stars5 days ago

This place was great! Very cozy and I have to say the best parts were the shower and AC Units 😂 I know it sounds crazy but it felt so nice after a long day in the sun to come in to a nice cool house! Appliances were very nice and up to date

5 out of 5 average rating, 80 reviews

Home in Marianna

Millstone on the Millpond-6 miles of Springs

TracyRating, 5 stars2 weeks ago

We highly recommend the Millstone on the Millpond! The house itself was amazing and perfect for our family of 4 trip. Kerri was very responsive to any questions and even checked on us to ensure we were good and didn't need anything. It was the perfect getaway for our family to celebrate our son’s 16th birthday. We enjoyed fishing from the pier and using the kayaks to explore the Millpond. Thank you so much for allowing us to enjoy your beautiful home!