Holiday rentals in Cypress

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Top-rated holiday rentals in Cypress

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Top 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
4.91 out of 5 average rating, 55 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.

Top 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.
Guest house in Chipley
4.96 out of 5 average rating, 414 reviews

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.

Top guest favourite
A spacious deck offers comfortable seating with woven furniture, including two chairs and a table. The view showcases the tranquil waters of Lake Seminole and the surrounding greenery, framed by trees that provide a natural backdrop.
Home in Donalsonville
4.97 out of 5 average rating, 31 reviews

Lake House Retreat

Nestled on the serene shores of Lake Seminole, this charming lake house offers an idyllic retreat for nature lovers and outdoor enthusiasts. The property boasts stunning waterfront views and direct access to the lake. The house features spacious living areas, modern amenities, and cozy, comfortable bedrooms, ensuring a relaxing stay. A public boat landing is 2 minutes away. Whether for a weekend or longer, this lake house on Lake Seminole promises a perfect blend of tranquility and adventure.

Guest favourite
A hot tub is set on a patio, with water illuminated in soft blue tones. Surrounded by a lush green lawn, it overlooks a serene pond and tall trees. A wooden deck is visible in the background alongside a grill, emphasizing outdoor leisure.
Home in Marianna
4.94 out of 5 average rating, 17 reviews

Merritt's Mill Pond Hideaway

Escape to our peaceful Merritt's Mill Pond Hideaway! Nestled on 2.5 private acres with 300ft of gorgeous waterfront, this rural retreat offers a balance of nature and comfort. Swim, kayak, or snorkel from your dock. Watch wildlife from deer to eagles, then marvel at starry skies so clear you'll spot the Milky Way. Just minutes from Florida Caverns State Park and a short drive to Jackson Blue Springs. A true North Florida gem where family meals and nature's soundtrack create memories that last.

Superhost
Home in Panama City
4.91 out of 5 average rating, 166 reviews

Beautiful 3 bedroom house quite neighborhood

Relax and enjoy your vacation days with your loved ones at this beautifully decorated, freshly remodeled house in a quiet neighborhood at the end of the street. Awake rested & refreshed in our top of the line beds along with ultra soft and comfortable bedding. The cozy & private master bedroom features king size bed with a premier purple mattress as well as a private exit through the master bathroom onto the screened in back patio. The furnished serene patio is also a perfect place to unwind.

Guest favourite
A screened-in back porch offers views of the lake and surrounding nature. The entrance features a wooden door and a welcome mat. Sunlight filters through the screens, casting gentle patterns on the floor. A lawn dotted with trees leads to the water's edge.
Cabin in Donalsonville
4.98 out of 5 average rating, 85 reviews

Fisherman's Lodge

This 3 bed, 3 bath house on Spring Creek at Lake Seminole is perfect for families or large groups of hunters and fisherman. It can comfortably sleep up to 12 people. Located less than a mile from Big Jim's Restaurant and boat ramp. This home has a fully equipped kitchen and two 65-inch TV's with YouTube TV. There is a gas grill outside and a fire pit that is perfect for relaxing evenings. You can dock your boat steps away from the screened in back porch or park it under the carport.

Guest favourite
A spacious bedroom is presented with a large bed adorned with a bright yellow throw. Two bedside lamps flank the bed, and a comfortable seating area includes two chairs. A patterned area rug lies beneath, and a dresser with a mirror is positioned against the wall.
Home in Brinson
4.96 out of 5 average rating, 57 reviews

Roomy, cheerful, 4-bedroom home near Bainbridge.

Bring the whole family to this clean, spacious home in the country. Enjoy the games, books and smart tv in the sunroom. The bathrooms have been updated with new tile in the showers. The small updated kitchen has all of the amenities. Relax while swinging on the back yard swing and grilling. There are 4 bedrooms and 4 full bathrooms. There is plenty of parking available so bring your boats for your hunting or fishing group to Lake Seminole, SpringCreek and the Flint River.

Superhost
A covered porch features a white swing and a charcoal grill, with dark flooring and tiled entry. The outdoor space is surrounded by lush greenery, providing a natural backdrop. Sunlight filters through the open area, enhancing the inviting setting.
Flat in Sneads
5 out of 5 average rating, 6 reviews

Three Rivers Stay 2

Centrally located to the intersection to Florida, Alabama, and Georgia. Close to Dothan, Tallahassee,Florida's beaches, Donalsonville,Bainbridge.Nearby recreational opportunities:Caverns, Merritt's Mill Pond, Chipola River, Chattahoochee River,Lake Seminole,3 Rivers State Park.Great local resaurants and brewery .Free Wifi, Smart TVs in each bedroom and the living room.Well equipped kitchen: Air fryer/toaster, stove,M/W, griddle.Laundry- washer&dryer.Boat parking. Fire pit.

Top guest favourite
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, 147 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 private 1/2 acre equipped with large smart TV's in both the living room and bedroom with Prime video.

Top guest favourite
A comfortable living area showcases a light-colored sofa and an accent chair, arranged around a wooden coffee table. A television is mounted on the wall above a decorative fireplace. In the background, a dining area features a large table surrounded by multiple chairs.
Home in Colquitt
5 out of 5 average rating, 51 reviews

Little City Farmhouse

Keep it simple at this peaceful and centrally-located cottage. Home built in 1910 and recently remodel to create a home the embelishes southern hospitality. Relax on the front porch 3 blocks from the town square and directly across from the new development by the hospital authority. Very quite even during the weekday buzz. Space designed for gatherings and friends.

Superhost
A single-story home is set against a backdrop of lush greenery. A green canoe rests on the grass in the foreground, while the house features a simple exterior with a covered porch. Windows allow for natural light, inviting the outdoors inside.
Cabin in Marianna
4.9 out of 5 average rating, 207 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.

Guest favourite
A cozy den area features a comfortable brown sofa and armchair, with two lamps providing soft lighting. A flat-screen TV is mounted on a rustic wooden wall adorned with a deer head mount. A plush area rug lies on the floor, adding warmth to the space.
Cabin in Greenwood
4.86 out of 5 average rating, 85 reviews

Country’s best, “Sweet Linda Lodge”

Get away from it all when you stay under the stars in this unique country cabin. Sit on any of 3 porches and enjoy the sunrises and sunsets over the tree lines while listening to the birds serenade . Leave the noisy city life and hectic daily schedules to escape to this cozy cabin in the country.

Popular amenities for Cypress holiday rentals

  1. Airbnb
  2. United States
  3. Florida
  4. Jackson County
  5. Cypress