Vacation rentals in Headland

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!

Peaceful cabin on the river amazing views & canoes

Enjoy the tranquility of this secluded river home situated on 8 acres. This unique property is directly on the Choctawatchee River with breathtaking views of the water. ⁃Beautiful nature trail on the property with ponds to fish ⁃fish the river from your backyard ⁃two canoes for your use ⁃large back deck is perfect for dining ⁃ camp fire area riverside ⁃ secluded and private -sleeps 8+ -freshwater spring boarders the property and flows into the river. Come and reset at the Magic Treehouse.

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;

Sedona Hideaway 3/2 Dothan, Alabama

1200 Sf of newly renovated comfort space in a quiet area on a cul de sac located in Dothan, Al ..convenient to Flowers Hospital &Southeast Alabama Medical Center, Fort Novasel & the Nuclear Plant. Golfing is at Highlands Golf Club . Shopping is close by and only 90 miles from the beautiful panhandle beaches of Florida. Three bedrooms with one KING & one QUEEN size bed & one FULL. Also enjoy a cozy private back patio with privacy fence. Two parking spots. Wifi, utilities, $ a streaming TV.

Sleeps 10 I Pet-friendly I Mins to Novosel

Located in the Valley Chase subdivision, this home offers a convenient and desirable location just minutes away from FT Novosel. With 3 bedrooms and 2 bathrooms, it is an ideal choice for TDY individuals or families relocating to Enterprise. Not only will you be close to Fort Novosel, but also the John Henderson Family Park. The entire home is exclusively yours to enjoy, and equipped with smart technology and enhanced security measures, allowing you to relax and make the most of your time.

Home in Heart of Headland

Quaint cottage located on the grounds of the beautiful and historical Covington Home that was built in 1902. Headland, AL better known as the “Gem of the Wiregrass” was rated one of the safest cities in AL in 2019 and is a designated Main Street community. The cottage is walking distance to the square where you will find soft music playing as you stroll the streets, picturesque oak trees, stylish boutiques and cuisine to fit any taste pallet. It is less than 10 miles to the Dothan Airport.

Great New Place to Stay for Families!

Newly renovated 2 bedroom 2 bath townhome was designed with love and thoughtfulness to help make your stay the best possible. Located just minutes from the Ft. Rucker gate and even closer to Enterprise shopping and dining. This unit was designed with care, guests will have access to a garage, in-unit laundry, a quaint back yard, 2 SmartTVs, high-speed wireless internet access, and a fully loaded updated kitchen.

The Short Final-We welcome pets!

This beautiful home has so much to offer. Minutes from Ft. Novosel, shopping, dining, outdoor parks, and entertainment. This home sits in a beautiful neighborhood and within walking distance of a peaceful neighborhood pond. Features include a saltwater pool(open year round),hot tub, small garage gym, 3 bedrooms, 2 baths. Fully stocked coffee bar! Kid & pet friendly. Garage parking with extra parking.

River Retreat in Geneva, Alabama

Nestled along the picturesque banks of the Choctawhatchee River, our charming River House in Geneva, Alabama, offers a serene escape from the hustle and bustle of everyday life. Whether you're seeking a peaceful weekend getaway or a longer vacation, this river house promises a rejuvenating experience like no other. Read on to discover what makes this property a hidden gem in the heart of the South.