Entire home

Jenny’s Southland Homestead, LLC

Photo gallery for Jenny’s Southland Homestead, LLC

A spacious living room with a grand piano, a chandelier, and a staircase leading to another level. - Jenny’s Southland Homestead, LLC (Bowling Green)
A pool table with a wooden backdrop, a chandelier, and a window with blinds. - Jenny’s Southland Homestead, LLC (Bowling Green)
A bright hallway with white walls, wooden flooring, wicker chairs, and a bed with a red bedspread. - Jenny’s Southland Homestead, LLC (Bowling Green)
A dining area with a table set for four, a ceiling fan, and a view of the outside. - Jenny’s Southland Homestead, LLC (Bowling Green)
A large, symmetrical building with a central entrance flanked by two wings, each with a brick facade and white trim. - Jenny’s Southland Homestead, LLC (Bowling Green)
Jenny’s Southland Homestead, LLC provides amenities like a playground and laundry facilities.

Reviews

9.8 out of 10
Exceptional

Entire home

5 bedrooms5 bathroomsSleeps 10534 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
  • Outdoor Space

Add dates for prices

About this property

Jenny’s Southland Homestead, LLC

  • Billiards Table | Game Room w/ WFH Desk Space | 11 Mi to Mammoth Cave National Park

    Built in 1914, this historic Victorian house in Bowling Green is the perfect vacation rental for large families. The house boasts 6 Smart TVs, a sitting room/library with 2 glassed-in porches, beautiful farmland views, and more. There’s a piano for the musically inclined, a fully stocked kitchen for the family chef, and 5,750 square feet of space — enough for everyone to spread out.

    -- THE PROPERTY --

    Warren County Short-Term Rental License: WC0021

    SLEEPING ARRANGEMENTS
    - Bedroom 1: 1 king bed
    - Bedroom 2: 1 full bed
    - Bedroom 3: 1 king bed
    - Bedroom 4: 1 king bed
    - Bedroom 5: 1 queen bed
    - Additional Sleeping: 1 pack 'n play

    SHARED OUTDOOR LIVING
    - In-ground seasonal pool (mid-April to mid-Oct)
    - Gazebo & dining area
    - Fire pit

    INDOOR LIVING
    - 6 Smart TVs (living room & bedrooms)
    - Billiards table & game room w/ WFH desk space
    - Washer & dryer
    - Piano
    - Gas fireplace
    - Books & board games
    - Dining table

    KITCHEN
    - Stove/oven, dishwasher, microwave
    - Keurig coffee maker, slow cooker, blender
    - Toaster, hand mixer, ice maker
    - Cooking utensils, pots & pans, spices
    - Dishware & flatware

    ACCESSIBILITY
    - 5 steps to enter, 1st-floor bedroom & shower

    PARKING
    - Shared driveway (6 vehicles)

    ADDT’L ACCOMMODATIONS
    - An additional property is available on-site with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to booking

    -- THE LOCATION --

    - Historic Victorian house w/ beautiful farmland views in Bowling Green
    - 3 miles to Trans Park Bowling Green
    - 11 miles to Mammoth Cave National Park
    - 11 miles to Western Kentucky University & National Corvette Museum
    - 13 miles to Beech Bend Park
    - 18 miles to Barren River Lake
    - 75 miles to Nashville International Airport

    -- REST EASY WITH US --

    Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

    -- POLICIES --

    - No smoking
    - No pets allowed
    - No events, parties, or large gatherings
    - Additional fees and taxes may apply
    - Photo ID may be required upon check-in

    ADDITIONAL INFORMATION
    - Addt'l rental on-site (separate unit) w/ access to shared pool
    - The seasonal pool will open for the season in mid-April and close in mid-October

Property amenities

Pool/Spa

  • Private pool

Internet

  • Available in the house: Internet access

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Microwave
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 4.5 bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table
  • Separate dining area

Entertainment

  • Books
  • Games
  • TV

Outdoor areas

  • Barbecue grill
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near a health/beauty spa
  • Near the marina

Things to do

  • Hunting nearby
  • Motor boating nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher

General

  • Unit size: 5,750 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 18

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

About the neighborhood

Oakland is home to this vacation home. National Corvette Museum and Historic Railpark and Train Station are cultural highlights, and some of the area's landmarks include Eloise B Houchens Center and Riverview at Hobson Grove. Looking to enjoy an event or a game while in town? See what's happening at Beech Bend Park or NCM Motorsports Park. Motor boating offers a great chance to get out on the surrounding water, or you can seek out an adventure with hunting nearby. Visit our Oakland travel guide
View more Vacation Homes in Oakland
Map
Bowling Green, KY

What's nearby

  • A red vintage car on display with a Mobilgas sign in the background.
    National Corvette Museum
    12 min drive - 15.9 km
  • Ephram White Park
    8 min drive - 8.3 km
  • NCM Motorsports Park
    13 min drive - 17.9 km
  • Bowling Green Ballpark
    16 min drive - 21.1 km
  • Southern Kentucky Performing Arts Center
    16 min drive - 20.8 km

Restaurants

  • Grammie's Home Cookin'
  • McDonald's
  • Wendy's
    14 min drive
  • Popeyes Louisiana Kitchen
    7 min drive
  • Wendy's

Frequently asked questions

Is Jenny’s Southland Homestead, LLC pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Jenny’s Southland Homestead, LLC?

Check-in begins at 4:00 PM.

What time is check-out at Jenny’s Southland Homestead, LLC?

Check-out is at 10:00 AM.

Where is Jenny’s Southland Homestead, LLC located?

Situated in Oakland, this vacation home is within 9 mi (15 km) of Ephram White Park, National Corvette Museum, and NCM Motorsports Park. Mammoth Cave National Park and Green River are also within 12 mi (20 km).

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Jenny’s Southland Homestead, LLC Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 25 out of 29 reviews
Rating 8 - Good. 4 out of 29 reviews
Rating 6 - Okay. 0 out of 29 reviews
Rating 4 - Poor. 0 out of 29 reviews
Rating 2 - Terrible. 0 out of 29 reviews

9.8

Cleanliness

9.8

Location

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful home

The home was impressive. We enjoyed being there and having plenty of room for a large family. Loved the pool as well.
Stayed 2 nights in Jul 2024
From a partner site

10/10 Excellent

huge house close to mammoth caves

Large, rambling historic house. Fit our party of 8 without any issues. Would recommend for a mammoth cave national park visit!
Stayed 2 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing and Relaxing

Everyone in our group loved this house! There is something special about Victorian style houses. This was a great place for a mini reunion. The kitchen had the cookware we needed for preparing our meals. I hope we can stay again.
Stayed 2 nights in Oct 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Vacation 2024

—Mammoth Cave Historic Tour —Pontoon Rental at Barren River State Park —Hanging out at the inground pool at our mansion home for our stay! —Dinners and games around the massive dining room table. —Lovely space, more bedrooms than 9 of us needed, responsive host, grill outs, beautifully decorated old home that we called “The Plantation”
Stayed 4 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Historical home in Bowling Green

We enjoyed our stay in this lovely home. It was just as described and suited our 8 person family gathering perfectly. The grandchildren loved the pool during the hot July days. It is the perfect location for a Bowling Green-Mammoth Cave adventure. Our hosts were wonderful and answered every question very quickly. We would highly recommend this house!
Stayed 4 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Grooms family

We stayed with our extended family for our son’s wedding. Wonderful historic home with plenty of room for everyone. We had 10 adults and had room for more. And everyone had a bed ( no fold outs ). Great experience.
Stayed 3 nights in Feb 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location

Beautiful Historic Home

We loved this house. It was very well put together and the location was perfect- plenty of space to enjoy the grounds and still close to food and the caves. Only downside was the pool was not open. I really wish that was made known before booking as that was a big reason why we booked this house. The host was very kind and accommodating. Thank you for a great stay!
Stayed 4 nights in Mar 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome Southern Estate

This was a beautiful historic home on an expansive property. Plenty of room for ten adults and beautifully decorated. Nice welcome gifts were on site at check in, all amenities provided, communication with owner was prompt and service was exceptional. Our adult kids enjoyed the pool, we had 2 beautiful sunsets and crystal clear starry skies at night. It was hot outside, but AC worked well, even though this is a historic renovated home. We would stay here again in a heartbeat. Well worth the fee for our 3 day stay.
Stayed 3 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Delightful

A charming and palacial home with luxurious bedding and beds. The original fixtures are well maintained and create an old world charm to the house. The expansive yard is great for family games of tag, football, soccer, etc. The house was aesthetically decorated for Christmas, with a tree in every bedroom. I highly recommend staying.
Stayed 4 nights in Dec 2023
From a partner site

10/10 Excellent

Great Historic Home and Great Hosts

I felt like a kid visiting their grandparents house, in the best possible way. Everyone loved the house! The house has been maintained so well and upholds the integrity of the historic style. The treats in the fridge were such a sweet and special surprise that everyone enjoyed. The hosts were prompt with communication and very friendly. The pool was fun for the kids. It was so peaceful sitting on the porch in the morning drinking my coffee. AC works very well in the heat of the summer for an older house! I would highly recommend staying here, you won't be disappointed!
From a partner site

10/10 Excellent

Beautiful Historic House

This home was exactly as we expected. Historic and beautiful with amazing furniture. It was easy to access and our host kept in touch with notifications. The master bedroom is beautiful with so much space. The only thing I would keep in mind is the bathrooms are old as expected and there is a strict limitation on the amount of visitors. This should not be an issues because it is communicated upfront. The kitchen is updated with new appliances and well stocked with everything you need and coffee. We would definitely stay there again if we visit the bowling green area. And if you have a wedding at Tayvin Gardens this is the perfect place as it is only 10 minutes away.
Stayed 2 nights in Oct 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Getaway

If you are looking for an exquisite getaway with the feel of a small Biltmore Estate, you've found the perfect location in this beautiful private mansion. The huge front porch with massive columns beckons you to a luxurious experience as soon as you arrive. Welcome to a relaxing stay complete with billiards, an inground pool, gorgeous chandeliers, and 5 stunning bedrooms, 3 with on suites. The host left several upscale unexpected surprises for us and was absolutely wonderful and extremely responsive when we had questions Bring your family for an unforgettable getaway where you can step back in time while still enjoying all the amenities of today. You will enjoy laughter around the firepit, special time together around the colossal dining room table, and fresh air together on the farm. This is a phenomenal place to reconnect and close to many attractions that Bowling Green has to offer, including lakes, caves, and other activities. If you're thinking about booking a stay here, you should do it now. We are grateful we had this amazing experience and all ten of us would have stayed forever if we could.
Stayed 3 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful farm setting just outside of downtown Bowling Green. The house has a lot of character in a good way. Plenty of parking.
Stayed 7 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
A really memorable property!
Stayed 3 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lisa was amazing and very helpful! Great stay and we loved the home!!
Stayed 3 nights in Aug 2025
From a partner site

10/10 Excellent

Had a wonderful experience

This house was awesome. Stayed in the pink room and it was beautiful to see the sunrise from our window. Thank you to the hosts for our lovely stay. Hope to return. I forgot to sign the guest book.
From a partner site

10/10 Excellent

The best home

We loved this house so much! The gorgeous rooms and history made it the perfect stay for my family. We also loved the pool. We can’t wait to stay here again
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house is great for large parties!! So many rooms. Large spacious living areas and bedrooms! It’s an old Victoria home with lots of character, so some of the doors stick a little, locks may not work, and not all plugs work (although there are a TON of plugs everywhere so there was plenty)! Used for a family wedding weekend house and with it being only 6 min from wedding site, it couldn’t be more perfect. And the pool was a great energy release for the little kids!! Will be returning when we come to visit for the holidays :-)
Stayed 4 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family vacation in Kentucky

We loved our stay. The house and property were beautiful. Having the inground pool was a plus. There was plenty of room for our family to have their own space and to enjoy the outdoors and pool.
Stayed 4 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Vacation

Great historical house, peaceful location, easy access to everything. Had a great stay with the kids and grandkids
Stayed 4 nights in Apr 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place for an extended weekend

Had an extended weekend with a group of 8 friends and everything was great
Stayed 4 nights in Jun 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Friends get-away

Fabulous place to gather with friends. So spacious and beautifully decorated.
Stayed 3 nights in Mar 2024
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Thanksgiving away

Beautiful home felt like a museum and host where very easy to communicate with any concerns during our stay
Stayed 6 nights in Nov 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing

Unbelievably geourgous home. Our stay was wonderful
Stayed 4 nights in Sep 2023
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice place

Beautiful house, but needs some minor repairs. A little farther from places than we thought, but pretty central between Mammoth caves and Bowling Green.
Stayed 4 nights in Jul 2024