Vacation Rentals By Owner In Enterprise, AL

Escape to The Pilot's Parlor, a stylish and comfortable 2-bedroom 2.5 bathroom townhouse perfectly set up for your next adventure. Inspired by the Golden Age of Aviation and designed for modern comfort, our home offers a unique and relaxing experience. Just a short drive from the Fort Rucker gates and minutes from the best restaurants and shopping in beautiful Enterprise, come and enjoy your stay with us!

The Pilot's Parlor 2BR/2.5 Bath townhouse 7 min to base

Enterprise, Alabama, United States

Bed

Bath

Sleeps

Exceptional(5)

$199.34

The Woodland Retreat on Crestview is named that because of its peaceful location central to everything you need in Enterprise or on Fort Novosel. A quick 5 minute drive to downtown or the Rucker Blvd gate gets you to where you need to go. Nestled in an established family friendly neighborhood, this home has 3 bedrooms and 2 bathrooms, enough for the whole family/coworkers to spread out. It's the perfect place to recharge as you listen to the wind blowing through the trees in the backyard.

Woodland Retreat 3 BR/2 bath home 5 min to base and downtown

Enterprise, Alabama, United States

Bed

Bath

Sleeps

Exceptional(4)

$141.36

Discover the charm of Enterprise from this 2-bed / 2-bath home. brIt is walking distance to Enterprise State Community College, ESCC Baseball and Softball parks. brWe are across the street from the NEW Soccer fields, Beach Volleyball, and Disc Golf. We are less than 1/2 mile from the NEW Pickle Ball courts.brbrEach bedroom features comfortable queen beds, with two full bathrooms. Large yard - big enough to have your own football/soccer game. brbrTwo-minute drive to the NEW Baker Performing Arts Center. brFour-minute drive to Downtown Enterprise - shopping, dining, festivals. brTen-minute drive to Johnny Henderson Park. brThirteen-minute drive to Fort Rucker. Great TDY location.brbrEnjoy all Enterprise has to offer while staying at our home!brWe are close by if you need anything during your stay.

Baseball and softball fans!!! Two-bedroom near Enterprise State Comm. College.

Enterprise, Alabama, United States

Bed

Bath

Sleeps

Exceptional(2)

$98.03

Welcome! We would love to host you at our comfy two bed one bath apartment in Enterprise. Ideally located in a quiet area in close proximity to shops and restaurants. Also only 5.5 miles (approx 10 mins) from Fort Novosel. brbr Enjoy a large parking lot, two smart TV's, fast internet, a desk with network connected printer, and a full kitchen. We look forward to your visit!

Blissful Bungalow- Near Ft. Novosel and shopping, Quiet, Fast WiFi

Enterprise, Alabama, United States

Bed

Bath

Sleeps

Exceptional(3)

$222.08

Welcome to your charming home nestled under the shade of a magnificent, mature magnolia tree, this delightful house offers the perfect blend of Southern comfort and unbeatable convenience. With just a 5-minute drive to everything Enterprise has to offer (restaurants, entertainment) you'll spend less time commuting and more time enjoying your stay. Whether you're here for military business, visiting loved ones, or exploring the Wiregrass region, this centrally located gem is your ideal retreat.

Southern Magnolia 3BR/2Bath Home 5 min to base

Enterprise, Alabama, United States

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Bath

Sleeps

$197.55

Enjoy your personalized stay with extra added touches at our highly sought after, safe, immaculate and centrally-located 2 bdr 2 1/2 bath townhome. Enterprise’s hidden gem has the most to offer and is peaceful and never crowded!! Furnished 2 story townhome with a one car garage, full size washer and dryer, high speed WIFI with wall-mounted tv’s in every room equipped with ROKU stick (no cable TV). Swimming Pool, Tennis Court, Basketball Court and clubhouse with Gym in complex. Perfect for short-term or long-term assignment. Only a 5 min. drive to Ft Rucker gate(3.2miles).

Quiet and Chic Country Retreat

Enterprise, Alabama, United States

Bed

Bath

Sleeps

$79.94

Escape to The Cabin, a cozy one-bedroom retreat with custom log-cabin siding that brings rustic charm indoors. Enjoy a fully equipped kitchen, modern bathroom, and comfortable bedroom with a vintage secretary desk perfect for work or journaling. Step outside and make use of the nice firepit area or gas grill that is ready for use. Nestled in a peaceful country setting, just minutes from town, this warm and inviting space offers the perfect balance of comfort, convenience, and log cabin charm.brbrAlthough the apartment is on the property with the main house, it is at the far corner of the lot (4 acres). This is not just someone's extra space in their home, it was designed and built for this purpose. I take great pride in ensuring the place is thoroughly cleaned and disinfected between guests. brbrGuests are given their privacy and space, although I am available to answer questions and address any concerns.brbrApartment is accessed with four digit code which will be given to the guest prior to arrival. I am available to help at check in, however guests may arrive after hours and access the apartment on their own...brbrThis is a second story apartment. Although a cargo elevator is provided for your luggage and anything else you don't want to carry up the stairs, guests must be able to negotiate stairs safely. If you have any small children you must take responsibility for their safety.brbr** PLEASE READ BELOW REGARDING CARGO LIFT**brThe cargo lift is provided to move inanimate cargo only. If you use the cargo lift for any other purpose you assume all risk and liability in the event you or your agents or representatives are injured or killed, personal property is damaged, or any damage results to the Landlords property.brbrbrPet Policy-brI get a lot of requests to make an exception to my policy of not allowing pets. Not only do I need to protect my investment, but I need to consider those that may have pet allergies. With all the carpet, and leather couch, this apartment is simply not suited for animals.br br**Security Cameras*brThe parking area and most if not all of the outside common areas are monitored by a security system. Of course, there are absolutely No cameras or microphones inside the apartment.brbr**EV Charging**brA Level 1 -110v 20a outlet is available for a small fee, upon request, for EV charging. Guest is a responsible for providing proper adapter for their vehicle. Guest should make contact with me prior to booking, or at least prior to arrival to ensure availability and access.brbr**Cleanliness note**brIn between guests we wash and dry at High heat ALL bedding. Many VRBO hosts, and most hotels, do not wash bed cover often. They often use big fluffy comforters that look great in pictures but are impractical and difficult to wash. We use fleece blankets that are warm, comfortable, and very easy to wash. We also ALWAYS wash all bathroom floor mats, and ALWAYS clean and disinfect all hard surface floors. I was surprised to discover how many people out there simply sweep in between guests, and only wash bathroom mats when they look dirty. The best indicator of how well a host cleans is the feedback from their guests. If you were to read through all of my feedback, on this and my other properties, you will note there are zero complaints about cleanliness. That is something I take great pride in and work hard to maintain.

The Cabin, cozy apartment in country setting

Enterprise, Alabama, United States

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Bath

Sleeps

$169.27

Relax with the whole family at this peaceful place to stay just minutes to everything you need! Only 5 minutes to base or to downtown Enterprise for shopping or restaurants, you will be in the heart of everything! This 3 bedroom 2.5 bath townhouse has 2 queen beds and 1 twin bed and 2 single foldout ottoman beds with large closets and enough relaxing space for the whole family. A community pool is available from May-Sept and the clubhouse has a small gym to work out in.

Peaceful 3 BR/2.5 bath*5 min to base*pool*

Enterprise, Alabama, United States

Bed

Bath

Sleeps

Exceptional(4)

$99.22

This newly remodeled apartment is ideal for a quick visit to Enterprise or for an extended stay in the area. Conveniently located directly across street from a Publix (grocery store) shopping plaza and just a few minutes away from restaurants, Wal-Mart (1.5 mi), and the military base (8 mi). br br- Easy self-check in & outbr- Comfy beds (king, full, and twin)br- Room darkening curtains for an undisturbed sleepbr- Washer/Dryerbr- Ample free parkingbr- Smart TVs with popular streaming services includedbr- High Speed internetbr- Fully equipped kitchen, ideal for long staysbrbrNo Pets and No Smoking

Enchanting Oasis - Centrally located! Quiet, great TDY spot, family friendly.

Enterprise, Alabama, United States

Bed

Bath

Sleeps

$44.61

This is a small studio apartment in a pole barn built above a wood shop. The pictures are pretty accurate even though they were taken with my phone. The Eagles Nest is perfect for someone just looking for a clean, comfortable and economical place to shower and lay their head at night.brbr I have 4 premium apartments on the other side of the property. This studio is not managed to the same high standards as those, but i take no shortcuts when it comes to functionality, safety and cleanliness.brbrApartment has a queen size pillow top mattress, 55 Roku TV with Spectrum premium cable and multiple streaming apps.br brKitchenette includes a microwave, air fryer, toaster oven, toaster, crock pot, Keurig style coffee maker, single burner, utensils, flatware, dishes, glasses and pot/pan.

The Eagle's Nest. No Frills Private Studio. Clean, cheap, laundry, firepit/grill

Enterprise, Alabama, United States

Bath

Sleeps

$181.06

Picture this: You've just landed in Enterprise, dropped your bags, and within 20 minutes you're floating in the pool (open May thru Sept) with a cold drink in hand — the Alabama sun warming your shoulders and zero plans for the rest of the evening. That's what Novosel's Nest is for. Pull in, park in your private garage, and immediately feel at home. brbr— ABOUT THIS SPACE —brbrThis 2-bedroom, 2.5-bath townhome is designed to feel like your permanent home base in Enterprise — not just a place to sleep. The layout flows naturally from the moment you step inside: open living area anchored by a comfortable couch and flat-screen TV, a fully stocked kitchen with a drip coffee maker ready for your morning routine, and a dining space that fits the whole group. The kitchen has everything you need — pots, pans, silverware, and all the essentials. Mornings are easy here.brbrbrbrUpstairs you'll find two generously sized bedrooms, each thoughtfully set up for real rest. The 2.5 bathrooms mean no waiting and no negotiating. The back patio is the quiet end-of-day spot — a coffee in the morning, a beer in the evening, your choice. And when the Alabama heat calls for it, the community pool is steps away.brbr— LOCATION & WHAT'S NEARBY —brbrYou're in the heart of Enterprise, Alabama — the Wiregrass Region's most connected small city. Fort Rucker is approximately 5–8 minutes away, making this the go-to spot for TDY visits, PCS house-hunting trips, and family visits to stationed soldiers. The famous Boll Weevil Monument is 5 minutes downtown. For food, Tacos Way or Hibachi and a Wing and downtown Enterprise's growing restaurant row are all within 10 minutes. Walmart, Publix, and major grocery options are 5–7 minutes away. For a fun evening, check out Par and Pour Indoor Golf Simulators — one of Enterprise's best group experiences.brbr— WHO THIS HOME IS BEST FOR —brbrThis home is ideal for military families visiting Fort Rucker — whether for TDY, training, a graduation ceremony, or a PCS house-hunting trip. It's also perfect for couples or small groups wanting a comfortable base for exploring the Wiregrass Region, business travelers who need a real home instead of a hotel room, and families looking for an affordable, well-equipped retreat with pool access.brbr— GUEST ACCESS —brbrYou'll have full, private access to the entire townhome. Check-in is at 3:00 PM and check-out is at 11:00 AM. Entry is completely contactless — your door code will be sent before arrival. The YALE smart lock means no keys to worry about or lose. Need anything during your stay Reach out anytime and we'll respond quickly.brbr— PARKING —brbrPark in the private garage or the driveway right out front — both are yours for the duration of your stay. No hunting for street parking, no permits needed.brbr— HOUSE RULES —brbrThis is a strictly smoke-free property. No cigarettes, vapes, cigars, or any smoking of any kind inside the home or on the property. Violation results in a $250 fee plus additional remediation costs — we appreciate your respect for this policy. Quiet hours after 10:00 PM to 8AM.

Rucker's Retreat 2 BR Townhouse *Pool* 5 min to Fort Rucker

Enterprise, Alabama, United States

Bed

Bath

Sleeps

Exceptional(5)

$139.2

Work, TDY, graduations, traveling nurse, visiting family, or just passing through...enjoy the peace and comfort of our cozy stand-alone farmhouse, no sharing of walls or crowded streets for parking. Relax on our deck and listen to the birds while you start your day or unwind after a busy day. At night enjoy the fire pit where you can sit and relax. We are 1/2 mile from Freedom Dr. and less than three miles from the Enterprise Gate which is open 24/7 to Fort Rucker. This is the perfect location, literally a 5-10 minute drive to whatever your needs may be. Our farmhouse has been in our family since 1943. It is safe, cozy, private, peaceful, and recently renovated. Once surrounded by farming land, there are still remnants of the farming past nearby. Although a smaller home, our home is more spacious than you'd expect, there are only two bedrooms which will sleep four people very comfortably and one bathroom with a shower/tub combination. The living room area is spacious and includes a large television for viewing live TV, movies on demand or whatever your streaming desires may be. There's a full kitchen with numerous amenities. The kitchen is open to the dining area which has a large table with six chairs. A coffee bar provides a Keurig Duo for whatever your hot beverage preference may be. There's a room in the center of the home which has a desk for working from and bookshelves filled with books, puzzles, cards and board games. Our laundry room is spacious and will allow you to pack less and have clean clothes when you return home or to your next destination! There's a front porch to relax on and you'll definitely hear birds chirping, and if you're up early enough, you might hear the neighbor's roosters crowing. The location is very close to all the airfields, easy access to both the Daleville Gate and the Enterprise Gate. It's very convenient to the aviation museum, which is a must see and it's only 30 minutes from the Dothan Regional Airport if you're flying into town. We're even close to the beaches, only 1 1/2 hour from Panama City Beach, the world's most beautiful beaches. Our farmhouse could be your home away from home. We hope you'll enjoy what our place in Enterprise has to offer. It's located on a paved county road on over an acre of land.

Country House

Location, Location, Location!! Cozy Farmhouse Very Close to Ft. Rucker

Enterprise, Alabama, United States

Bed

Bath

Sleeps

Exceptional(3)

$211.87

Located in the heart of Enterprise, welcome to our cozy modern home!! This home sits on the top of a hill which creates its cozy and peaceful setting. The 3 bedroom 2 bathroom home has desks in the master and 1 guest bedroom to allow travelling professionals or small families a place to work and rest! All new furnishings purchased in January 2025, this home is modern yet relaxing! Enjoy a home cooked meal or sit on the patio and BBQ, this home has it all!

Cozy Modern Home- 3BR/2 Bath 5 min to base

Enterprise, Alabama, United States

Bed

Bath

Sleeps

Exceptional(7)

$199.12

Casa Linda on JasminebrbrYour Home Away From Home in EnterprisebrbrWelcome to Casa Linda on Jasmine, a charming retreat thoughtfully designed to blend luxury and comfort in the heart of Enterprise, Alabama. This beautifully appointed 3-bedroom, 2-bathroom home offers the perfect escape for families, military personnel visiting Fort Rucker, or groups of friends seeking a relaxing and memorable stay.brbrAccommodationsbrbrCasa Linda comfortably sleeps up to 6 guests with premium bedding configurations:brbr1 King Bed in the master bedroombrbr2 Queen Beds in the additional bedroomsbrbrEach of the two bathrooms is equipped with modern amenities, including bathtubs and hair dryers, ensuring your comfort and convenience throughout your stay.brbrPrime LocationbrIdeally situated near downtown Enterprise, Casa Linda places you within easy reach of:brbrThe city's finest dining establishmentsbrbrLocal shopping destinationsbrbrPopular attractions and entertainmentbrbrFort Rucker - just a short drive away, making this the perfect choice for military families visiting loved onesbrbrWhat Makes Casa Linda SpecialbrbrEvery detail of this charming home has been carefully considered to create a cozy, elegant space where you'll truly feel at home. The thoughtful design combines modern luxury with warm, inviting touches that make your stay comfortable and memorable.brbrPerfect ForbrMilitary families visiting Fort RuckerbrbrSmall groups and gatheringsbrbrFriends traveling togetherbrbrAnyone seeking a peaceful retreat with easy access to Enterprise's amenitiesbrbrBook Casa Linda on Jasmine today and discover your home away from home in Enterprise, Alabama!

Casa Linda on Jasmine

Enterprise, Alabama, United States

Bed

Bath

Sleeps

$169.84

Welcome to Southeast Alabama Daydreaming. As you walk into this 3 bedroom 2.5 bathroom townhouse minutes from downtown Enterprise and Ft Rucker, you will be reminded of childhood days gazing into the sky looking for clouds that looked like your favorite animal. We provide all the modern conveniences to make your stay effortless. High-speed Wi-Fi, a fully equipped kitchen, soft linens and comfortable furnishings mean you can relax without a worry.

Alabama Daydreaming 3BD/2.5 bath *5 min to base*pool

Enterprise, Alabama, United States

Bed

Bath

Sleeps

$217.92

Welcome to Winterberry, a stylish and comfortable retreat in Enterprise, AL. Perfect for families and military stays, this home sits in a quiet neighborhood just minutes from downtown, the base, restaurants, shopping, and the golf course. Whether you’re here for work, relocation, or a relaxing getaway, Winterberry is the perfect place to feel at home. Planning a longer stay Message us about extended‑stay discounts.

Winterberry- Manor 3BR King+Queen 85TV Base

Enterprise, Alabama, United States

Bed

Bath

Sleeps

Exceptional(6)

$153.28

Welcome to Chillin' at Foxchase. This home is conveniently located right outside Ft. Rucker (Enterprise Gate) and minutes from Downtown, and Boll Weevil Circle . lt's also only about an hour and half away from the world's most beautiful beaches, the Gulf of Mexico. With 2 bedrooms and 2.5 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.brThe spacebr⁘ Open concept living space.br⁘ Minutes away from FT Rucker via Enterprise gate.br⁘ Downtown restaurants and shopping destinations located just a short distance away.br⁘ Keyless entry and self-check-in.br⁘ Stay connected with complimentary Wi-Fi.br⁘ Security with Nest outdoor cameras, thermostat, and doorbell camera. (1 backyard, 1 driveway and a doorbell camera)br⁘ Log in to your favorite streaming services during your stay via the TV's ROKU guest mode.br⁘ Spacious comfy couch, perfect to relax and unwind.br⁘ Fully kitchen equipped with all necessary appliances and cookware.br⁘ Essential toiletries to include, 100% Vegan, Cruelty-Free, Paraben & Sulfate-Free Shampoo, Conditioner, Hand Soap, Lotion, and cotton towels.br⁘ Park your vehicles in the driveway with space for up to 4 vehicles (2 in driveway and 2 in the street)br⁘ Gather around the dining room table for enjoyable meals.br⁘ Dedicated office space outfitted with a adjustable desk.br⁘ Covered patio area for outdoor relaxation.br⁘ Garage is not available to guest.brbrGuest accessbrEnjoy complete access of the entire home, featuring 2 bedrooms and 2.5 full bathrooms. The sleeping arrangements include 1 Cal-king bed, 2 queen beds.brOther things to notebrChillin' at Foxchase, located in “Foxchase” subdivision. We enjoyed this quiet and relaxing neighborhood, and hope you do also. The neighborhood has a STRICT 20MPH speed limit, please respect it as its a family friendly neighborhood with family's taking walks with pets to kids playing in the streets.brbrwill collect your funds upon booking and release them to the host 24 hours after their scheduled check-in time. If you are active duty, we can provide a zero balance receipt after your reservation to assist with lodging reimbursement.brbrState, county, and city taxes are assessed/remitted as well as an active license is required to have this great unit available for your stay.brbrThe front door has an easy-to-use keypad and a Ring doorbell for security along with 1 camera in the backyard, 1 camera in the driveway (ALL 3 CAMERAS ARE WORKING & RECORDING)

Chillin' at Foxchase 2BR/2.5BA

Enterprise, Alabama, United States

Bed

Bath

Sleeps

Exceptional(54)

$262.26

This home is conveniently nestled in the Valley Chase subdivision in Enterprise, AL. just minutes from Fort Rucker, John Henderson Family Park, and the Enterprise Country Club. brbr- Open-concept living space filled with modern decorbr- Minutes to FT Rucker via Faulkner and Enterprise gatesbr- Minutes to popular restaurants and shopping downtownbr- Keyless + Self Check-in br- Free Wifi br- Two exterior security cameras one in the front door doorbell and the second on the left corner of garage overlooking the driveway. br- 4 SmartTV able to to log in to all popular apps Netflix, HBO etc…( with personal account) br- Ultimate streaming trio Disney+, ESPN+, and Hulu provided for all our guests br-Beds include Purple and Tempurpedic-quality mattressesbr- Cozy couches to relax or nap br- Full kitchen w/Microwave oven br- All kitchen appliances and cookware perfect for a relaxing meal br- The Bathrooms include essential toiletries and plush cotton towels.br- Driveway + Garage parking br- Dining room w/ seating + additional barstool sitting in kitchen bar br- Dedicated Office space for business travelers.br-Covered patiobr- Weber Spirit E-210 Black 2-Burner Liquid Propane Gas Grill

Sleeps 10 I Pet-friendly I Mins to FT Rucker

Enterprise, Alabama, United States

Bed

Bath

Sleeps

$260.14

Bring the whole family to this great place with lots of room for fun. Home features Fully equipped kitchen with cook wear and spices if you enjoy home cooked meals. Has game room with foosball table, air hockey table, and paceman arcade games. Every bathroom is stocked with shampoo, soap, and toothbrush/ toothpaste. Minutes away from Fort Rucker, shopping centers, and restaurants with a 1h 45m drive to Panama City beach. Perfect for large families, small groups or peaceful getaway.

Large spacious Home

Enterprise, Alabama, United States

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Bath

Sleeps

Most popular vacation rentals in Enterprise

$98.03

Blissful Bungalow- Near Ft. Novosel and shopping, Quiet, Fast WiFi

Enterprise, Alabama, United States

Bed

Bath

Sleeps

$141.55

Pet Friendly/ Minutes from Fort Novosel w/Pool Access

Enterprise, Alabama, United States

Bed

Bath

Sleeps

$141.36

Baseball and softball fans!!! Two-bedroom near Enterprise State Comm. College.

Enterprise, Alabama, United States

Bed

Bath

Sleeps

$139.20

Country House

Location, Location, Location!! Cozy Farmhouse Very Close to Ft. Rucker

Enterprise, Alabama, United States

Bed

Bath

Sleeps

$125.34

Something Simple, a great place to relax

Enterprise, Alabama, United States

Bed

Bath

Sleeps

$119.87

Boll Weevil Cottage

Enterprise, Alabama, United States

Bed

Bath

Sleeps

$114.57

Matriarch Manor-Chic Comfort Near Base + Pool Access

Enterprise, Alabama, United States

Bed

Bath

Sleeps

$84.23

\"The Lodge\"- APT w/Loft Bedroom, Walnut Bar, Quiet Setting, Covered Parking

Enterprise, Alabama, United States

Bed

Bath

Sleeps

$78.85

\"The Sanctuary\" -Custom built Apartment, 1 BR, Covered Deck, Country Setting.

Enterprise, Alabama, United States

Bed

Bath

Sleeps

$79.94