Enterprise holiday lettings

We found 74 holiday rentals — enter your dates for availability

Discover a selection of 38 homes, 16 apartments and other holiday rentals in Enterprise that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday rentals have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a fireplace. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.

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Choose a holiday rental for your Enterprise getaway

Learn about the unique charm of Enterprise with a stay in a holiday home rental. This city's sightseeing, cafes and local tours draw many visitors. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Enterprise

Are you hoping to discover attractions to visit during your stay? Venture out of your cosy holiday rental and experience everything that Enterprise has to offer. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Tartan Pines Golf Club (1.4 mi / 2.2 km)
  • Silver Wings Golf Course (9.9 mi / 15.9 km)
  • River Oaks Golf Course (19.8 mi / 31.9 km)

Exploring the natural landscape of Enterprise

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Enterprise is a great place to get out in nature. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Beaver Lake (9.4 mi / 15.2 km)
  • Frank Jackson State Park (24.7 mi / 39.7 km)
  • Lake Helen (12.6 mi / 20.3 km)
  • Sam Dale Park (17 mi / 27.3 km)
  • ED Lisenby Lake Complex (17.2 mi / 27.7 km)
  • Constitution Oak (20 mi / 32.3 km)

Transport options to and around Enterprise

Fly into Dothan, AL (DHN-Dothan Regional), the closest airport, located 24 mi (38.6 km) from the city centre.

Frequently asked questions

What is the best area to stay in Enterprise when booking a holiday rental?
When considering a holiday rental in Enterprise, Alabama, the downtown area is an excellent choice. This vibrant neighbourhood offers a charming blend of local shops, restaurants, and cultural attractions, making it an ideal spot for both relaxation and exploration. Among the highlights in downtown Enterprise is the stunning Boll Weevil Monument, a unique tribute to the cotton industry that has become a symbol of the city. Additionally, visitors can enjoy the picturesque parks, such as the Enterprise City Park, which provides lovely walking paths and picnic areas.

Another appealing area to consider is the vicinity around the historic district, where you can find beautifully preserved homes and a rich sense of history. This area is great for those who appreciate architecture and the stories behind the buildings. It is also close to the popular Army Aviation Museum, showcasing a remarkable collection of military aircraft and offering insight into the region's aviation history.

In terms of accommodation, Enterprise has a variety of properties available, suiting different budgets and preferences. Whether you're looking for a cosy cottage or a spacious home, you're likely to find a suitable option in these delightful neighbourhoods that provide easy access to both attractions and local amenities.
How much does it cost to rent a holiday home in Enterprise?
Prices for holiday rentals in Enterprise vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Enterprise to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Enterprise holiday house rentals?
You can find great discounts on house rentals in Enterprise on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Enterprise?
In Enterprise, holiday houses are the most popular type of holiday rental, with approximately 108 available throughout the area. These homes typically offer spacious living arrangements, featuring multiple bedrooms, fully equipped kitchens, and outdoor spaces—ideal for families or groups looking for comfort and convenience. Additionally, there are around 42 apartments, which provide a more compact option for travellers seeking a home base in the city. These apartments generally include essential amenities such as kitchen facilities and cozy living areas. There are also several charming cottages available, adding to the variety of options for a more quaint and rustic experience.
Are there any family house rentals in Enterprise?
In Enterprise, Alabama, there are numerous family-friendly house rentals available—approximately 21 options throughout the area. This charming town is known for its welcoming atmosphere and access to local attractions, making it an excellent choice for families. Many of the properties feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play and explore. Common amenities include Wi-Fi and air conditioning, ensuring a comfortable stay for everyone.

Visitors can enjoy nearby points of interest, such as the charming downtown area with its unique shops and restaurants, as well as the Enterprise State Community College, which often hosts events. The local parks, like the picturesque Johnny Henderson Park, offer playgrounds and picnic areas, great for family outings.
Can I rent a holiday home with a pool or hot tub in Enterprise?
In Enterprise, Alabama, there are several holiday homes available for rent that feature pools and hot tubs, providing a great way to relax during your stay. The area offers a mix of charming neighbourhoods, where you can find properties that cater to various group sizes, great for families or friends. Many of these rentals come equipped with amenities such as private pools, outdoor patios for lounging, and fully equipped kitchens, ideal for enjoying home-cooked meals. Some may also include additional features like barbecues and spacious gardens, enhancing your outdoor experience.
Can I find long-stay holiday rentals in Enterprise?
A long-stay holiday rental in Enterprise is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Enterprise?
In Enterprise, Alabama, there are several pet-friendly house rentals available, with around twenty options to choose from. Many of these holiday homes are equipped with essential amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces, superb for families or groups travelling with pets.

The area has an inviting space for pet owners, with local parks like the Enterprise State Park, which features walking trails and open spaces where pets can enjoy the outdoors. Additionally, the nearby Johnny Henderson Park provides further opportunities for leisurely strolls and picnics, making it a great spot for pets and their owners to relax together.
Are there any remote work holiday rentals in Enterprise?
In Enterprise, Alabama, there are plenty of options for remote work holiday rentals, with approximately 138 available. The town offers a selection of properties that cater to those seeking a work-friendly environment. Many of these rentals come equipped with essential amenities such as free Wi-Fi, ensuring a reliable internet connection for work tasks.

Travellers can expect various types of accommodations, ranging from cosy apartments to spacious homes that often feature dedicated workspaces or comfortable areas for setting up a laptop. Additionally, properties typically include amenities like fully equipped kitchens for cooking meals and relaxing living spaces, allowing for a balanced work-life experience during your stay.

The town itself is known for its friendly atmosphere and is conveniently located near local parks and recreational areas, providing opportunities for outdoor breaks and relaxation after a day's work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Enterprise holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Enterprise with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Enterprise?
In Enterprise, popular holiday rentals typically include a variety of amenities to enhance the stay. Most properties come equipped with kitchens, allowing guests to prepare their own meals, while onsite parking is commonly available for convenience. Many rentals feature decks or patios, providing outdoor spaces to relax or enjoy meals al fresco. Additionally, coffee and tea makers are standard in most accommodations, suiting those who appreciate a warm beverage at any time. Some properties also permit pets, making it easier for travellers to bring their furry companions along.
When is the best time to visit Enterprise for a holiday rental?
The best time to visit Enterprise for a holiday rental is during the peak season from May to July. This period is particularly vibrant, as visitors flock to the area to experience the warm Southern hospitality and partake in outdoor activities. With temperatures typically ranging from the mid-20s to low 30s Celsius, the sunny weather is superb for exploring local parks, enjoying the scenic views, and engaging in fun-filled family activities.

July stands out as the most popular month, where you can mingle with fellow travellers and immerse yourself in the lively option of community events and festivals. Notable attractions include the beautiful gardens and historical sites that Enterprise has to offer, all within a comfortable distance for easy sightseeing.

For those seeking a more budget-friendly option, consider visiting in November. This quieter month provides a wonderful opportunity to enjoy the charm of Enterprise without the hustle and bustle of peak tourist season. You can take leisurely strolls through the local parks and appreciate the beauty of the autumn foliage.
How early should I book a Enterprise holiday rental?
Book your Enterprise holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Enterprise?
In Enterprise, Alabama, visitors can explore several top attractions that reflect the town's charm and history. The Boll Weevil Monument, located in the heart of downtown, is a unique tribute to the cotton industry and is a symbol of the town's resilience. Nearby, the Enterprise State Community College features beautiful grounds and offers cultural events throughout the year.

For outdoor enthusiasts, the Little Choctawhatchee River provides opportunities for fishing, kayaking, and leisurely walks along its banks. The city is also home to the Army Aviation Museum, showcasing the rich history of Army aviation and featuring various aircraft exhibits, making it a fascinating stop for history buffs.

Additionally, visitors can enjoy the local parks, such as the gorgeous Johnny Henderson Park, which has walking trails, picnic areas, and playgrounds, ideal for families looking to relax outdoors.
Can I change or cancel my Enterprise home rental booking on Vrbo?
To find Enterprise holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Enterprise holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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