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Holiday houses in Headland

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Top-rated holiday rentals in Headland

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Townhouse in Dothan

4.79 out of 5 average rating, 168 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 favourite

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 favourite

Tiny home in Headland

4.99 out of 5 average rating, 90 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 favourite

Cottage in Blakely

4.97 out of 5 average rating, 38 reviews

Cottage in the Woods that Sleeps 10

Raven’s Rest is nestled on 3 wooded acres in Cedar Springs, Georgia, a stone’s throw from the historic town of Blakely and the majestic Chattahoochee River. This newly renovated 2-bedroom, 1-bunkroom, 1-bath, 1-outdoor shower, cottage comfortably sleeps 10 people. We cater to weekend hunter and outage worker groups, as well as families and executives. With few lodging options in our area, Raven’s Rest is a versatile property that can accommodate many different lodging needs.

Guest favourite

Townhouse in Enterprise

5 out of 5 average rating, 53 reviews

J&Y Family 3BR/2.5BA / LuxuryTownhouse

We know how important it is to feel comfortable & relaxed when you arrive back from a long day of sightseeing. This idea is what inspired us. We want to provide a place to recharge, relax and enjoy. All the modern appliances, smart Technology and security with thermostat and Exterior security camaras on property. Your family will be close to everything: Downtown, Shopping,Restaurants and 4 miles to Fort Rucker.

Townhouse in Enterprise

4.8 out of 5 average rating, 40 reviews

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.

Guest favourite

Home in Enterprise

4.85 out of 5 average rating, 33 reviews

Spacious Townhome Retreat - Mins to Ft Novosel

Welcome to the Retreat on Baldwin! This 2 bedroom 2 1/2 bath townhome is the perfect place to call home while visiting Enterprise. Centrally located - only 5 minutes from Fort Novosel and close to all the great restaurants and shopping Enterprise has to offer. Located in a quiet neighborhood right of Rucker Blvd. The community swimming pool and exercise room is right across the street - no need to drive!

Guest favourite

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 favourite

Tiny home in Slocomb

4.98 out of 5 average rating, 133 reviews

Comfortable Tiny House In Wicksburg

Comfortable tiny home in Wicksburg, Alabama offers a loft with a queen size bed. The downstairs has another sleeping area that includes a twin size sleeper sofa. The spacious kitchen has new appliances. There is a scenic view for a peaceful stay, but only about 1 hours drive from places like Panama City Beach Florida. Also, Dothan is 14 miles and Ft Rucker is 12 miles away.

Guest favourite

Home in Dothan

4.94 out of 5 average rating, 36 reviews

Southside Shanty

Outside the hustle & bustle of traffic, yet still close to everything! We are located: • 3 miles from James Oates Park • 4.5 miles from Southeast Health • 5.5 miles from ACOM • 8 miles from Flowers Hospital • 8 miles from Westgate Park/Tennis/BMX • 6.5 miles from Wiregrass Public Safety Center • 5 miles from center of town/courthouse • 28 miles from Fort Novosel

Guest favourite

Home in Enterprise

4.88 out of 5 average rating, 8 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

Guest favourite

Apartment in Enterprise

4.95 out of 5 average rating, 76 reviews

Very clean, spacious w/ a beautiful view

Located in a nice neighborhood, just outside Novesol gate in Enterprise. 6 minutes from Daleville, 25 minutes from Dothan, and 20 minutes from Ozark also 90 minutes from the beach. Please do not book if you want to party. This is a quiet neighborhood,thanks!

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Free parking on premises

Air conditioning

Other great holiday rentals in Headland

Guest favourite

Home in Enterprise

4.99 out of 5 average rating, 71 reviews

Lovely Residential Ranch Home with KING bed

Guest favourite

Home in Columbia

4.85 out of 5 average rating, 13 reviews

Mayberry on Main

Guest favourite

Home in Columbia

4.96 out of 5 average rating, 23 reviews

Green Acres Farmhouse

Guest favourite

Tiny home in Ashford

4.94 out of 5 average rating, 67 reviews

Barndo“mini”um

Guest favourite

Barn in Slocomb

4.89 out of 5 average rating, 47 reviews

Zeke’s House: Bed & Barn Bliss

Guest favourite

Home in Headland

4.81 out of 5 average rating, 21 reviews

Gazebo House

Guest favourite

Home in Dothan

5 out of 5 average rating, 13 reviews

Hannah's Cottage

Guest favourite

Cottage in Dothan

4.99 out of 5 average rating, 173 reviews

Juju’s Pond House on Smith Pond

Destinations to explore