Vacation rentals in Calhoun County

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Top-rated vacation rentals in Calhoun County

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

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Guest favorite

Guesthouse in Chipley

4.96 out of 5 average rating, 186 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, two twin bunk beds, and a queen size sleeper sofa, all of which can accommodate a total of 6 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 guests.

Jan 18 – 25

R1,560 ZAR per night

Guest favorite

Cottage in Marianna

5.0 out of 5 average rating, 85 reviews

Quiet, cozy 1 bdrm cottage near Caverns & Bear Paw

No cleaning fees! Peaceful and quiet golf cart friendly location yet the I-10, 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, & Panama City within 1 hour. Modern cottage on a 1/2 acre is equipped with large TV's in both the living room and bedroom w/ HBO, Prime, Hulu. The living room has a pull out couch with a mattress topper for extra comfort on request

Jul 28 – Aug 4

R2,376 ZAR per night

Guest favorite

Home in Marianna

5.0 out of 5 average rating, 24 reviews

Lake House near Marianna & Panama City FL

Enjoy a beautiful, serene, restful atmosphere inside & out at this fully equipped lake front home. Amenities include a fully equipped home with linens, towels, kitchen equipment, washer, dryer, a private dock reaching into deep water, kayaks and water toys for your enjoyment. Perfect for family or a group of friends. Excellent fishing & swimming. No gas motors allowed, allowing the spring fed lake to stay pollutant free. RV hook ups & dump station with plenty of parking also available for fee.

Jul 24 – 31

R3,869 ZAR per night

Guest favorite

Home in Donalsonville

4.98 out of 5 average rating, 129 reviews

The R & R Lake House on Lake Seminole

Fish, Hunt, Grill, or Chill with direct access to the big lake in just 8 minutes by boat.. Lake Seminole contains 37,500 acres of water, and a shoreline of 376 miles. Bass-Masters annual event attracts anglers from all 50 states. The fish include largemouth bass, crappie, chain pickerel, catfish, striped bass and others. Home is nicely decorated with a lake theme. Awesome Sunsets and views of the lake from the screened-in porch, backyard, 80ft dock, and boat house.

Aug 12 – 19

R2,831 ZAR per night

Guest favorite

Guesthouse in Port St. Joe

4.96 out of 5 average rating, 246 reviews

Carriage House on the Beach

This is a roomy 500 square foot (46 m2) bright and airy studio with full bath. The beach is just a half-mile away; an easy walk or a very short drive. Attached to a seldom-used two-car garage, it is super quiet, completely private, and very clean. Your hosts are a retired couple who live on-site in a detached residence. English and German spoken. Pets (one dog only) welcome with prior coordination. Late check in is NOT available; we will meet you at the door.

Jul 5 – 12

R2,058 ZAR per night

Guest favorite

Guest suite in Panama City

4.95 out of 5 average rating, 208 reviews

Mother-in-law studio near St. Andrews

This is a newly remodeled studio apartment in Panama City. It is less then 1 mile to the restaurants in St. Andrews and is 20 mins away from Panama City Beach. It has a queen size bed, 1 bathroom and a small kitchen; great for two people. Everything in the apartment is brand new. It also has a covered patio with furniture for lounging. This is a small and cozy place but has great access to all the activities in the area. Wifi with Amazon Prime is included.

Aug 13 – 20

R1,799 ZAR per night

Guest favorite

Guesthouse in Panama City

4.99 out of 5 average rating, 107 reviews

Ivy Palms Retreat Pool House-Low Cleaning Fee!

This is the perfect little affordable getaway spot! It is a very quiet retreat that is close to downtown Panama City, Historic St. Andrews, and only a short drive to the beach! The best of all worlds!! Has it's own parking space and private entrance. Perfect for a couple as it only has one queen size murphy bed with use of the pool, hot tub, & outdoor kitchen! We prefer no children or pets for liability reasons since the pool itself is not fenced.

Aug 30 – Sep 6

R2,808 ZAR per night

Guest favorite

Tiny home in Marianna

4.9 out of 5 average rating, 393 reviews

Live Simply Entire Tiny House/Shed conversion

***Extra Care Taken To Protect You!**** Live Simply- This 12 x 24 Tiny House/shed conversion is a perfectly private, quaint little space for your business traveling needs or your weekend getaways offering A/C, heat, refrigerator, microwave, small kitchenette for meal prep with a hot plate and microwave. Two comfy recliners to relax and have some popcorn while watching your Netflix, Prime or Hulu favorites. Also available for longer stays, just ask!

Jul 30 – Aug 6

R1,820 ZAR per night

Guest favorite

Home in Marianna

4.93 out of 5 average rating, 44 reviews

"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.

Nov 28 – Dec 5

R2,407 ZAR per night

Guest favorite

Home in Altha

4.99 out of 5 average rating, 82 reviews

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.

Feb 24 – Mar 3

R2,959 ZAR per night

Guest favorite

Guest suite in Panama City

4.8 out of 5 average rating, 178 reviews

1 bed1 bath studio apartment 4 miles from beach!

1 bedroom 1 bathroom studio apartment 4 miles from beach! Very safe and quiet neighborhood . Great for 1-2 guest only! Living area, kitchen , tv and wifi provided! Own private entrance and single car driveway. Great rental for business travelers and vacationers! Cheap, clean and safe ! Absolutely smoke free unit !! No smoking inside unit !

Jun 26 – Jul 3

R1,872 ZAR per night

Guest favorite

Cabin in Marianna

4.93 out of 5 average rating, 169 reviews

A beautiful place

Located on the Chipola River in historic Marianna, Fl. 2 canoes available for your use. Large deck you can fish from. Dock on the river for swimming or launching canoes. Home of the World famous Florida Caverns State Park. Also one of Florida's biggest blue holes "Blue Springs". Only 1 hour from Panama City Beach.

Jul 7 – 14

R2,924 ZAR per night