Holiday rentals in Samson

Beautiful and Spacious 3 BR/2BA with KING bed

Our "Home Sweet Home" is a beautiful full residential 3 BR/2 full BA home in a quiet family-oriented neighborhood. Master BR: 1 King bed, BR has jacuzzi tub 2nd BR: 1 Queen bed 3rd BR: 2 Twin beds Living room: Comfortable sofa and optional rollaway bed if needed, 55" Smart TV with all the streaming apps, kid games Kitchen: Fully Stocked Coffee Bar, cookware, double oven, microwave, dishwasher, plates, glasses, wine glasses and more. Garage: 2 car private Entry Way: Keyless Entry Pet Friendly

Location · Family · Layout

Come Chill at our Cute 2 bedroom Cottage

Enjoy yourself in this completely renovated and remodeled cottage located in the heart of Enterprise, AL. This space has been designed with the guest in mind. We offer full kitchen, laundry, high speed fiber optic internet, and all new furnishings in this modern take of an original WWII era home. We aim to please and, although new to Airbnb, we have hosted over 1000 - 5 Star trips on other P2P platforms. You'll love coming back to the Come Chill cottage. New Pickleball Courts 3 min away!

Value · Family · Kitchen

Whispering Woods

Come enjoy Serenity and Nature Three Bedrooms and two full baths, living and dinning room, functional kitchen. Plenty of room to stretch out, relax and enjoy. Yard space to Bar-B-Cue or just watch the stars. 17 miles from the magnificent Ponce De Leon Springs and a short 13 mile drive to The Vortex Springs, 25 miles from stunning Cypress Springs and approximately 35 miles to the shores of Santa Rosa Beach, Seaside, or Grayton Beach State Park. Divers, Springs and nature enthusiasts Welcome!

Location · Kitchen · Accuracy

Relax at the Ridge | 4BR/3BA

Welcome to Relax at the Ridge. This home is conveniently located right outside Ft. Rucker (Faulkner Gate) and minutes from Downtown, and Johnny Henderson Park. lt is also only about an hour and half away from the world's most beautiful beaches, the Gulf of Mexico. With 4 bedrooms and 3 bathrooms, it has plenty of room for families visiting Enterprise. The entire home is exclusively yours to enjoy. Equipped with smart technology and enhanced security measures, this could be your perfect stay.

Family · Value · Amenities

Legacy House in Opp/Andalusia/Elba/Florala

Legacy House is a restored 3-bedroom, 2-bath home in Opp, Alabama, featuring vintage furnishings that honor its 1930s roots. Relax on the cozy front porch, cook in the fully stocked kitchen, and enjoy washer/dryer access and wifi. Close to shops, dining, and outdoor activities, it offers comfort, charm, and convenience. Operated by survivors of domestic violence and human trafficking, your visit helps provide job training and employment opportunities. Book now and support a lasting legacy!

Location · Family · Parks

Experience Historical Charm at ‘The White House’

Experience Historical Charm at The White House. Sleeps 9 guests, four bedrooms, 5 beds, and 2 couches. Plan a day trip to Panama City Beach, Florida, or to local Springs or State Parks. Check out our Guidebook. Enjoy small town charm away from the hustle. Relax on the front porch at the founding Historic cornerstone of Samson. Kids can play hide and seek outside away from their screens on the 2-acre lot. Gather around the fire pit and roast s’mores. A short walk to restaurants downtown.

Value · Family · Comfort

Stay Awhile | Peaceful Small-Town Escape

Welcome to your home away from home! Nestled in the heart of Geneva Alabama, our charming short-term rental offers the perfect blend of comfort, style, and convenience. Geneva is home to Robert Fowler Park AKA "The Junction" where the Choctawhatchee River and Pea river join. We are only 2.6 miles from the park. We have plenty of parking if you want to bring your boat. 11 miles to Samson 34 miles to Dothan 23 miles to Enterprise 27 miles to Ft. Rucker 60 miles to Florida beaches

Family · Location · Indoor spaces

Perfect for Big Families, Sleeps 14, Fort Rucker A

Located in one of Enterprise, AL's finest neighborhoods, Cotton Creek, this 4 bedroom home offers an exceptional stay. With 3 King beds, 4 Full beds, 2 queen sleeper sofas, and 2 baths, it's ideal for larger families on a PCS or visiting Enterprise. Just minutes away from Fort Rucker, John Henderson Family Park, and the Enterprise Country Club. Enjoy the convenience of smart technology and security throughout the entire home, allowing you to unwind and make the most of your time.

Family · Value · Pets

Casa Linda | Spacious & Beautiful | 2 King Beds

Welcome to Casa Linda on Jasmine — a beautiful, spacious 3-bedroom home featuring 2 King beds + 2 Full beds, perfect for families, groups, military stays, and extended visits. Enjoy a comfortable, stylish home just minutes from downtown Enterprise, restaurants, shopping, the golf course, and a short drive to Fort Novosel. Planning an extended stay? Ask about our monthly discounts. Dates unavailable? Message us — we may have another beautiful home available nearby.

Family · Location · Quiet

Boothe Pond Cabin on East Fork Creek

Beautiful pond cabin on a secluded dirt road along the popular route to 30A beaches. Fishing available from shore and the property includes a small boat launch, fire pit, porch swing, rocking chairs, grill, and picnic tables. A full kitchen and cabin amenities in a picturesque setting. This is a great place for family to get away or to stop by and rest while traveling south the the beaches. Bedroom 1 has queen size bed and bedroom 2 has full size bed.

Value · Location · Accuracy

The Cove on Juniper

The Cove on Juniper Take a break and unwind at this peaceful oasis lakefront property. This cozy retreat offers a perfect blend of tranquility and adventure, making it an ideal getaway for families, friends , or solo travelers. Enjoy stunning sunsets from our lakefront fire pit. Paddle the lake in one of our two canoes or fish from our backyard dock. If you're in the mood for exploration, take a drive and discover the many springs in the panhandle.

Location · Value · Kitchen

Haven of Rest

Come relax with your family to this city of two rivers where dwells Alabama's oldest and largest live oak tree. Called the Constitution Oak, it is said to be over 300 years old and was alive at the signing of our nation's constitution. Situated in the midst of Geneva, and only 70 miles from the beach, this two bedroom one bath house will give you that Alabama spirit and allow you and your family to enjoy a little get away in the south.

Value · Family · Grill