Holiday rentals in Greenwood

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

4.95 out of 5 average rating, 340 reviews

Guest house in Chipley

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.

5 out of 5 average rating, 145 reviews

Peaceful & Beautiful Lake Cabin, Boat House/Dock

Located on beautiful Lake Seminole, a short distance from the hosts main house. Includes use of boat house & dock (you'll need your own boat). 2 boat landings within a mile. Across the lake from Lake Seminole State Park. Within 2 miles of gas station, Dollar General & restaurant. 45min to FL ST Caverns. Free wifi. Full Kitchen is equipped with dishes, pots pans, full size oven/range, refrigerator, microwave, coffee maker. Large flat screen TV, screened in porch and back deck near fire pit

Superhost

4.88 out of 5 average rating, 208 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.

Guest suite in Enterprise

4.98 out of 5 average rating, 559 reviews

BEST VALUE - No Cleaning Fee

"Relaxing, calm, quiet, peaceful"--all used to describe the 1,200 sq. feet of guest space attached to our home--Read a complete description under "The Space." The private guest suite includes a family room, two bedrooms and bath on our micro-farm just 4 minutes from Fort Rucker and Enterprise. Southern hospitality at its best--Read our reviews! Ammenities include personal-size fridge, coffee, microwave, pool table, WiFi, TV, DVD, Wii, games and toys; laundry room; Handicap/ADA accessible;

4.93 out of 5 average rating, 144 reviews

Home in Dothan

Twin Pines | Luxury Getaway

Welcome to Dothan's Gem! A beautifully designed dream home! Bringing the whole family? Working remotely? Rest assured, you'll have high speed internet no matter what, with speeds up to 500mbps! While there's plenty of privacy, this location makes it easy for you to get around You are only: 4 mins to Flower's Hospital 5 mins to Westgate Recreation Park 5 mins to Forever Wild Trails 10 mins to the heart of Downtown Dothan 1.5 hrs to PCB & surrounded by Dothan's best restaurants!

4.98 out of 5 average rating, 187 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.

4.99 out of 5 average rating, 195 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.

4.91 out of 5 average rating, 450 reviews

Flat in Dothan

Claire’s Cottage with privacy gate

Everything you need in a quaint, modern space located on 7 secluded acres with a privacy gate only minutes from the Ross Clark Circle and downtown, Wi-Fi, Smart TV with YouTube TV subscription included (over 70 channels), brand new fridge, spacious rooms. Washer and dryer available. We allow pets on a case by case basis and charge a one time $10 fee per pet upon guests arrival. We also offer EV level 2 charging (40 amp) for a flat $10 fee.

5 out of 5 average rating, 10 reviews

Home in Greenwood

The Willis House

Come forget about your worries at this peaceful 6 acre historic property built in 1917. The huge oak trees surround this property making it a built in canopy. This keeps the house cooler in the summer. Sit or walk around the 4500 square feet of porches and catch a breeze or sit and have quite time. The home has been recently remodeled and set to current fire code standards. The house has a lot of room to roam full upstairs and downstairs.

4.99 out of 5 average rating, 127 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.

Superhost

Cabin in Marianna

4.92 out of 5 average rating, 193 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.

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Greenwood holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Greenwood

4.96 out of 5 average rating, 54 reviews

Home in Pansey

Quiet, updated, Semi Country Home Outage friendly.

JenniferRating, 5 stars1 month ago

2nd time we have reserved David's place for a long term stay, will definitely stay again.

Superhost

Tiny home in Marianna

4.6 out of 5 average rating, 5 reviews

The Mockingbird Tiny Home

GregorioRating, 5 stars5 months ago

beutiful placer awsome People thank you

5 out of 5 average rating, 6 reviews

Farm stay in Ashford

Cozy Catalina RV Home

SoteraRating, 5 stars12 months ago

Stayed 2 weeks and was a great stay both weeks. very clean and close to my job. Very cheap and worth every bit of money. Sue was very friendly and if I needed anything, she was there to help with all my needs.

5 out of 5 average rating, 13 reviews

Terry’s Air B&B

SamanthaRating, 5 stars1 week ago

Wonderful place! Would definitely recommend and come back if in the area. Felt like home. Super small town. Hardly any civilization. Husband and I kept walking over to Sonny's supermarket. :) this was my mom's first Airbnb and she had an awesome experience. If you struggle with sleeping in silence, bring a fan or something that makes noise. I have a sound machine but when the ac kicked off I still heard everything. And it does get a little warm when the ac kicked off (if you need air always blowing on you like me) Otherwise, this was an awesome stay. Thank you so much!

4.97 out of 5 average rating, 35 reviews

Cabin in Donalsonville

Paradise Cabin

ElizabethRating, 5 stars2 months ago

Very responsive & easy to deal with.

4.95 out of 5 average rating, 55 reviews

Cottage in Bainbridge

Seminole Hideaway Cottage

DrewRating, 5 stars2 months ago

Spent a week here for a fishing trip. Steve greeted me with some fishing info while Sandra made sure everything was exactly what I needed. They gave full access to their boat doc and lift. Privacy is no issue here while you feel you can call for help or info at anytime. This is the place to be if you want easy access fishing. Or even just a calm relaxing time by the water. Step outside at night and listen to all the critters sing! These two have a great thing going.