Vacation rentals in Headland

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Top-rated vacation rentals in Headland

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Home in Enterprise

4.92 out of 5 average rating, 166 reviews

The LA (Lower Alabama) dream

Welcome to the L.A. dream! An adorable fully remodeled modern home with accommodations for the whole family or multiple families. No shortage of creature comforts with all new memory foam mattresses, high pressure showers, granite countertops, reclining sofas, 70in TV, strong A/C, screened back porch with seating. Kid friendly! With pack n play & high chair. Extra parking on back side of property with ability to accommodate a total of 5 cars. Located 10 mins to Ft Rucker gate, 2 mins to Publix

Guest favorite

Cottage in Enterprise

4.9 out of 5 average rating, 214 reviews

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!

Superhost

Treehouse in Hartford

4.85 out of 5 average rating, 53 reviews

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.

Guest favorite

Guest suite in Enterprise

4.98 out of 5 average rating, 530 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;

Superhost

Townhouse in Dothan

4.79 out of 5 average rating, 171 reviews

Feeling Beachy ~ 3BR/3BA Short & Long Term Stay

This spacious 2 story townhome, over 1,500 sq ft, sleeps 8 and is centrally located in Dothan, AL with multiple parking options. Located 5 minutes from both hospitals, RTJ+DCC golf courses, Westgate Recreation Park & Water World with area shopping and restaurants close by. Keyless entry for self check-in. Newly renovated and fully equipped kitchen, washer/dryer, fast/free wifi and more. Enjoy streaming your favorite movies and shows with our Roku TV. Short term & long term stays are welcome!

Guest favorite

Home in Dothan

5 out of 5 average rating, 7 reviews

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.

Guest favorite

Home in Enterprise

5 out of 5 average rating, 136 reviews

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.

Guest favorite

Tiny home in Headland

4.99 out of 5 average rating, 100 reviews

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.

Guest favorite

Home in Enterprise

4.9 out of 5 average rating, 137 reviews

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.

Guest favorite

Home in Hartford

5 out of 5 average rating, 15 reviews

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.

Guest favorite

Home in Dothan

4.9 out of 5 average rating, 10 reviews

Cozy Spyglass Hideaway 3 BR 2 Bath

Discover serenity at this 3-bed, 2-bath retreat near Flowers Hospital and Highland Oaks Golf Course. Enjoy a spacious living area, fully equipped kitchen, and cozy bedrooms with plush bedding. Relax on the private patio or explore nearby attractions and dining options. Ideal for medical visits or leisure, this home offers comfort and convenience in a quiet neighborhood setting

Guest favorite

Home in Enterprise

4.89 out of 5 average rating, 9 reviews

Briarwood super nice 2BR/2.5 BA townhouse

A very nice 2 BR/2.5 BA townhouse in a quiet neighborhood with community pool. Spacious, newly furnished. Smart 58 inch TV in living room , 43 inch in the master . Full stainless steel kitchen, washer and dryer. Free WiFi, free parking. Close to shopping, restaurants and Fort Novosel Base . Local manager with long experience in hosting. Book with confidence