Vacation rentals in Chipola River

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Top-rated vacation rentals in Chipola River

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Top 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, 418 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.

Guest favorite
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, 18 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.

Guest favorite
A relaxing outdoor space features four blue chairs arranged around a fire pit, set against a scenic lakeside view. The backdrop showcases a tranquil lake at sunset, with reflections of vibrant orange and purple hues in the water. Tall trees frame the area, enhancing the peaceful atmosphere.
Home in Donalsonville
4.88 out of 5 average rating, 223 reviews

“The Q'whack Shack" on Lake Seminole with Dock

Aptly named, “The Q'Whack Shack,” our quaint lakefront home is the perfect host accommodation for a charming weekend or weeklong reprieve. Ideally situated on the heart of Lake Seminole, The Q’Whack Shack is a water enthusiasts dream hideaway. Enjoy boating, angling, an array of watersports (skiing, tubing, etc.), grade-A bass fishing and duck hunting with convenient private dock access just steps from the back door. Waterfront restaurants and other provisions just a quick boat/car ride away.

Top guest favorite
The view from a large window showcases a vibrant sunset over the bay. Two Adirondack chairs are positioned on a deck outside, framed by palm trees. The tranquil waters reflect hues of orange and pink, creating a serene atmosphere.
Home in Panama City
4.94 out of 5 average rating, 216 reviews

Bay Beach Bungalow waterfront family vacation home

Bring the whole family to your waterfront getaway. Enjoy your own St. Andrews Bay Beach access, including your own dock. Experience over water dining, fishing, sunbathing, Kayaking, or SUP. Watch for birds, turtles and dolphins. Bring your own boat and anchor offshore, or rent a boat from the marina right across the street. This is a great family destination. Trust us with your vacation, relax and enjoy bay views, your own bay beach and space. Absolutely no weddings or parties are allowed.

Top guest favorite
Two blue Adirondack chairs are positioned on a wooden deck overlooking the water. A small table with a potted plant sits between the chairs, providing a comfortable place to relax. The calm bay and dock area can be seen in the background.
Cottage in Panama City
4.94 out of 5 average rating, 154 reviews

Water front bay beach and boat dock stunning views

Take it easy at this unique and tranquil getaway. Duplex is 550 square feet on the water. Fish from your backyard or end of dock. Catch breathtaking sunsets on the back deck. Private boat dock with slips Boat ramp 1/4 away. Kayak and explore East St. Andrews Bay. Location is very quiet and peaceful . Walk the shore to the Tyndal bridge and view wild life. 30 minutes to PCB. 18 miles to Mexico Beach. 3 mile to Tyndal Gate. Complementary kayaks/paddle board. Fishing charter option available!

Guest favorite
An aerial view of a riverside retreat showcases the vibrant orange exterior of the cabin, with spacious decks extending towards the water. Surrounding natural landscape is visible, providing a serene and inviting backdrop. The illuminated cabin reflects warmth during twilight.
Cabin in Altha
4.92 out of 5 average rating, 87 reviews

Breathtaking Luxury Riverside Retreat near Beaches

Experience enchanting nights under the stars and breathtaking views of the clean spring-fed Chipola River. Fish, swim, tube, kayak, snorkel...explore this beautiful Florida river any way you wish! “The World's most Beautiful Beaches" are just one hour away in Panama City, making this double-cabin home a true haven for nature lovers, fishing enthusiasts and beach bums alike. Whether you’re looking for a romantic getaway, family vacay, fishing or girls trip, this private retreat has it all.

Top guest favorite
A rustic studio cottage is set among tall pine trees, featuring a wooden exterior with large windows. A spacious deck is equipped with a pair of wooden chairs, inviting relaxation outdoors. The surrounding landscape displays natural vegetation with a blend of grasses and tree stumps.
Guesthouse in Wewahitchka
5 out of 5 average rating, 110 reviews

The Bunkie on Wetappo Creek

Enjoy a tranquil getaway in this cozy and comfortable studio cottage overlooking the water. Are you working remotely and looking for the perfect retreat space? A couple looking to leave it all behind for a bit and recharge? Come and enjoy the peaceful sounds of happy birds and whispering pines, all while being a short 15 minute drive away from the Gulf of Mexico and its white sand beaches. This private and peaceful space surrounded by Mother Nature invites you to relax and unwind.

Top guest favorite
A serene beach scene features a sandy shoreline gently leading to calm waters. A long wooden pier extends into the bay under a bright blue sky adorned with fluffy white clouds. Lush greenery is visible to the right, enhancing the natural shoreline.
Home in Panama City
4.96 out of 5 average rating, 199 reviews

3BR/2BA Bayfront Home w/prvt. bch. Dog friendly

We are located in the beautiful historic neighborhood of St. Andrews. This is not just a 3BR/2BA house for rent, it was the family home of the current owners . Newly renovated, it feels like a home away from home for guests. The house is fully stocked for comfort & is pet friendly. Private beach, huge bayside yard w/deck, incredible views day and night. Everything you need for supplies, dining, shopping and entertainment is within one to two miles of the house.

Top guest favorite
An outdoor deck area is furnished with colorful chairs, including a red and a blue adirondack chair. A small wooden table is placed between them. Potted plants add greenery, while a grill is partially visible in the foreground. The entrance door is located in the background.
Apartment in Panama City
4.95 out of 5 average rating, 407 reviews

The Pelican's Nest -Perfect Private Spot w/Views

The perfect getaway for vacation or business trip! Cozy efficiency 450 sqft. Queen bed, duel recliner sofa, flat screen TV, kitchenette, counter bar for eating or laptop use, bath w/shower. Antique wall cabinet storage. On 2nd floor w/private entry. Step out your door for bay views & old oaks surrounding you. Grill on your deck. Free paddleboards/kayaks/bicycles/fish off docks. Enjoy our new greenhouse too. Perfect spot for those seeking privacy.

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, 148 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 favorite
A cozy seating area features a dark gray sectional couch paired with a square ottoman. Decorative pillows are arranged on the couch, and a woven basket rests atop the ottoman. Light streams through a nearby window, illuminating the textured rug beneath.
Cabin in Calhoun County
4.98 out of 5 average rating, 45 reviews

Big Daddy and GiGi’s Happy Place

No parties allowed and no more than 4 guests allowed. Charming waterfront barndominium located on the beautiful spring-fed Chipola River in Altha, Florida. From its waterfront location to its outdoor amenities and entertainment options, this cabin is perfect for a truly unforgettable vacation experience. Whether you're seeking relaxation, adventure, or a combination of both, this property has it all.

Guest favorite
Illuminated palm trees frame a serene lakeside setting at night. A covered cabana sits nearby, featuring seating arrangements. Soft lighting gently highlights the landscape, reflecting on the water, while a grassy area offers space for relaxation.
Cabin in Panama City
4.89 out of 5 average rating, 119 reviews

Cabin on Private Beach with Tiki Bar & Cabana

3 Queen beds, 2 bedrooms, queen futon sofa. Lake front, tiki bar with swings, covered cabana. Gated property for privacy. 20 minutes from Panama City Beach. Ten minutes from Ecofina Springs. Stone tiki kitchen with fireplace, open fire Argentine grill and smoker. Beach side cabana with privacy shades, 10 inch mattress, 43 inch smart TV, wood fireplace.

Popular amenities for Chipola River vacation rentals

  1. Airbnb
  2. United States
  3. Florida
  4. Chipola River