Vacation rentals in Enterprise

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Top-rated vacation rentals in Enterprise

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Guest favorite
A covered patio area is highlighted by a comfortable seating arrangement featuring a woven coffee table and four cushioned chairs. Light wood paneling and a brick border complement the space, while a side entrance door adds access to the interior.
Guest suite in Enterprise
4.98 out of 5 average rating, 189 reviews

Downtown Private Suite

Enjoy your own private entrance into the home through the back patio, leading directly into a private living room with an attached master bedroom, bathroom and walk in closet. The home is centrally located near downtown Enterprise. Please note: This is a shared home; however, no living spaces are shared. A locked door separates both sections of the home to ensure complete privacy. Recreational drug use and smoking of any kind are strictly prohibited inside the home and anywhere on the property.

Guest favorite
Home in Enterprise
4.97 out of 5 average rating, 266 reviews

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

Top guest favorite
Home in Enterprise
5 out of 5 average rating, 12 reviews

The Byrd Nest in the Heart of Downtown Enterprise

Welcome to our little home away from home in the heart of Enterprise! Our century-old house blends historic charm with modern comfort and convenience. Just steps from downtown restaurants, shops, pubs, and local attractions, it’s the perfect spot for guests who want to experience everything the Boll Weevil City has to offer. And it's only a short drive to the Fort Rucker gate! Whether you’re visiting for work, family, or a weekend getaway, we’re excited to host you and hope your stay is great.

Top guest favorite
Apartment in Enterprise
4.99 out of 5 average rating, 309 reviews

"The Clubhouse" Pvt Apt w/Mstr BR & 2bed Kids Loft

I spent 2 years custom building this apartment to be used exclusively as an Abnb rental. It was handcrafted using tongue & groove pine milled here in AL. All of the oak/pine used for the trim, cabinet doors, and custom furniture were milled in VA using my stepfather's personal sawmill with lumber harvested both from my property here in AL, and my families property in VA. Even the door/drawer pulls and switch/outlet covers were hand forged in PA by an Amish guy at his home forge in his basement.

Guest favorite
Cottage in Enterprise
4.91 out of 5 average rating, 274 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!

Guest favorite
The exterior of a spacious country home is displayed, featuring a welcoming entrance framed by palm trees and lush greenery. The façade includes large windows and a central front door, with a driveway leading to the garage. A soft lawn surrounds the property.
Home in Enterprise
4.88 out of 5 average rating, 120 reviews

Pet-Friendly 4BR w/ Huge Fenced Yard- Near Rucker

Relax with the whole family at this country home in Enterprise. Enjoy the peaceful ambiance of a spacious backyard filled with charming landscaping and chirping birds! This four-bedroom two bathroom home comes fully equipped with Wi-Fi, a working space, a washer and dryer, a full kitchen, and a spacious backyard. Feel at home in our Country Gardens and enjoy the five-minute drive to downtown Enterprise for shops and restaurants. Also a short 18-minute drive to the FT. Rucker Enterprise gate.

Top guest favorite
Guest suite in Enterprise
4.98 out of 5 average rating, 634 reviews

BEST VALUE - No Cleaning Fee; "Clean & Peaceful"

"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;

Top guest favorite
The townhouse exterior features a brick façade with a garage door and a welcoming front porch. Large windows allow natural light to brighten the entrance, while neatly trimmed bushes frame the pathway leading to the front door.
Townhouse in Enterprise
4.97 out of 5 average rating, 160 reviews

Townhouse -convenient to Ft. Rucker-self check in

This 2 bedroom 2 1/2 bath townhouse is conveniently located 5 minutes from Fort Novosel and just minutes from the shopping areas and restaurants in Enterprise Alabama. It's packed with amenities to include 3 large TVs and High-speed wireless internet. The kitchen has all the necessities; dinnerware, silverware, knives, pots and pans, toaster, Kurig coffee maker, and more. We pride ourselves in hosting a place that we would want to stay in that has comfortable beds, very clean, and safe.

Top guest favorite
The exterior of the home features a well-maintained facade with a spacious driveway. A large attached garage is visible, along with neatly landscaped greenery. The house is set against a backdrop of trees, creating a serene outdoor setting during dusk.
Home in Enterprise
4.92 out of 5 average rating, 62 reviews

Home in the heart of Enterprise

Located in the heart of Enterprise, this home offers a convenient and desirable location just minutes away from Fort Rucker. Why would you pay for a hotel room when you can get a spacious house for almost the same price? With 3 bedrooms and 2 bathrooms, it is the perfect option for TDY individuals, families PCSing, or families attending AIT graduations. All destinations around are less than 10 minutes away. The entire home is exclusively yours to enjoy and relax the most of your time.

Top guest favorite
Home in Enterprise
4.99 out of 5 average rating, 157 reviews

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.

Guest favorite
Home in Enterprise
4.9 out of 5 average rating, 150 reviews

The Short Final-We welcome pets!

This beautiful home has so much to offer for someone looking for aTDY unit or a fully furnished home.. This home sits in a beautiful neighborhood and within walking distance of a peaceful neighborhood pond. Features include a saltwater pool(open year-round), a hot tub, a small garage gym, 3 bedrooms, and 2 baths. Fully stocked coffee bar! Kid & pet friendly .Close to Shell Field so you will see 🚁 Welcome to the home of Ft. Rucker and the sound of freedom!

Guest favorite
Townhouse in Enterprise
4.93 out of 5 average rating, 152 reviews

Modern 3BR Townhome Retreat - Close to Ft Rucker

Be our guest! Enjoy this 3 Bedroom, 2 1/2 bath townhouse conveniently located in the heart of Enterprise. You will be 9 minutes from Downtown Enterprise, 5 minutes from the Ft. Rucker Enterprise gate, 12 minutes from Boll Weevil Circle and only a 30 minute drive to Dothan. The home also includes a spacious backyard, one car garage and 2 driveways. Whether you’re here for a visit, in town for graduation, or PCS, our home is perfect for you.

Popular amenities for Enterprise vacation rentals

When is the best time to visit Enterprise?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$19,247 GYDG$18,829 GYDG$18,829 GYDG$17,783 GYDG$19,038 GYDG$19,666 GYDG$19,875 GYDG$18,829 GYDG$19,038 GYDG$18,829 GYDG$19,247 GYDG$19,247 GYD
Avg. temp9°C11°C15°C19°C23°C27°C28°C28°C25°C20°C14°C10°C

Frequently Asked Questions

  • What are the best places to stay in Enterprise?

    Explore stays around downtown Enterprise for easy access to restaurants, shops, and local culture. The neighborhoods near Main Street are often recommended for their proximity to popular attractions and community events.

  • What are the best things to do in Enterprise with kids?

    Families can explore city parks with playgrounds, participate in interactive museum exhibits, or visit locally rooted markets. Enterprise also has community centers that frequently suggest craft and activity sessions for children.

  • What are some of the best things to do in Enterprise?

    Explore the Boll Weevil Monument, take a stroll through local parks, and join seasonal events that celebrate the town’s agricultural heritage. Visiting area museums or browsing shops along Main Street are frequently suggested activities.

  • How is the weather in Enterprise?

    Enterprise has mild winters, ranging from 37–60°F (3–15°C), and warm, humid summers near 72–94°F (22–34°C). Spring and autumn often bring comfortable temperatures and lower rainfall, making these seasons popular for outdoor activities.

  • When is the best time to visit Enterprise?

    Spring and autumn are often recommended, with comfortable temperatures and fewer rainy days. Late spring is a favorite for seasonal festivals, while summer brings outdoor celebrations and lively community events.

  • What are the best places to visit in Enterprise?

    The Boll Weevil Monument is a frequently suggested landmark, and the local history museum has exhibits highlighting the region’s story. Parks around town and the historic downtown are popular for exploring local shops and dining.

  • What are some hiking trails in Enterprise?

    Enterprise has walking trails within city parks that feature shaded paths and picnic spots. For more wooded routes, explore nearby nature areas that offer gentle hikes suitable for most visitors.

  • What are some family activities we can do in Enterprise?

    Families can enjoy picnics at city parks, interactive experiences at local museums, or participate in community-led events like craft fairs and farmers markets. Seasonal activities such as outdoor movie nights are also frequently suggested.

  • What are some of the best day trip ideas from Enterprise?

    Explore nature reserves around Enterprise, visit nearby towns with historic sites, or discover regional museums and art centers. Outdoor enthusiasts can find lakes for fishing, hiking, or boating near the area.

  • Are there any pet friendly accommodations available in Enterprise?

    Enterprise has pet friendly accommodations, especially in neighborhoods close to parks and open spaces. Many stays welcome pets, making it easier to explore the area with animal companions.

  • What are some local tips for visiting Enterprise?

    Locals often suggest starting your day with a stroll through downtown, checking out community events, and visiting local markets for fresh produce. Lightweight clothing is practical during warmer months, and exploring historical landmarks provides context on the town’s roots.

  • What is Enterprise known for?

    Enterprise is known for the Boll Weevil Monument, representing its agricultural history and resilience. The community has a tradition of celebrating its heritage through festivals, markets, and regional food.

  • What are the best hidden gems to explore in Enterprise?

    Local art galleries and smaller museums often highlight creative works and regional stories. Quiet parks and community-led shops around historic downtown offer a glimpse into Enterprise’s distinct culture.

  • What are the best foods to try in Enterprise?

    Explore locally rooted flavors like Southern-style barbecue, fried catfish, and homemade pies. Many restaurants and markets have dishes inspired by regional farming traditions and seasonal produce.

  • What should I bring for a trip to Enterprise?

    Bring lightweight clothing for humid summers, a light jacket for cooler evenings, and sturdy shoes for walking downtown or exploring parks. A reusable water bottle and sun protection are practical additions for outdoor activities.

  • What is the nightlife in Enterprise like?

    Enterprise has lively venues with live music, casual bars, and community events held around the historic downtown. Local restaurants host evening gatherings, often with seasonal menus and entertainment.

  • What are the most popular events or festivals in Enterprise?

    The Boll Weevil Festival, often held in late fall, celebrates agricultural heritage with live music and food. Community fairs and seasonal farmers markets are frequently suggested, creating festive atmospheres throughout the year.

  • Are there family friendly vacation rentals in Enterprise?

    Many vacation rentals in Enterprise are family friendly, especially those near parks, community centers, and downtown. These accommodations typically have home-style amenities and easy access to area attractions.

Quick stats about vacation rentals in Enterprise

  • Total vacation rentals

    Explore 100 vacation rentals in Enterprise

  • Nightly prices starting at

    Enterprise vacation rentals start at G$8,368 GYD per night before taxes and fees

  • Verified guest reviews

    Over 6,020 verified reviews to help you choose

  • Family-friendly vacation rentals

    90 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    100 of Enterprise vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Enterprise rentals

  • 4.9 Average rating

    Enterprise stays are highly rated by guests—averaging 4.9 out of 5!

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