Family-friendly holiday rentals in Oak Grove

4.92 out of 5 average rating, 116 reviews

Cottage in Ashland City

The Little House by the Woods

Hunt, Hike & More! A tranquil retreat with all the comforts of home. Calming colors, lots of natural light. Enjoy Tennessee's natural beauty with a subtle homage to our favorite Gulf Coast beaches. "The Little House by the Woods" is on a ridge surrounded by trees. Across the road is Cheatham Wildlife Management Area with 20,000 acres of hill country with hiking, hunting and birdwatching. You'll have easy access to so many parks, recreation and all that Nashville (30 min. away) has to offer.

An outdoor seating area features a comfortable light-colored sofa adorned with a decorative pillow. A dark tabletop with a circular opening is positioned in the center. Two wooden rocking chairs are visible in the background, set against a brick wall.

4.92 out of 5 average rating, 209 reviews

Historic Downtown cottage FULL of Amenities

Take a break and unwind at this peaceful guest cottage located on historic Greenwood Ave. 1 mile from downtown and APSU, this quaint home is full of amenities and waiting for you! Enjoy cooking in the equipped kitchen,dine in front of the electric fireplace with remote settings. Plenty of games and Roku TV to pass your time. The queen bedroom is ideal for 2 adults while the living room has 2 twin ottoman beds available for kids. Full bath, laundry room, and a desk for the working professional.

The living room features a comfortable tan sectional sofa adorned with blue accent pillows. A wooden coffee table sits at the center, complemented by a decorative plant. Natural light filters through sheer curtains above two windows, enhancing the inviting atmosphere.

4.84 out of 5 average rating, 164 reviews

Happy Hidaway! Pets Welcome~Fenced Yard.

Welcome to our home! Less than 5 minutes from Ft Campbell gate 4, which offers convenience for military personnel. Just 10-mile distance to Austin Peay State University and 4 miles from I-24, our house provides easy access to Kentucky, Alabama, or Georgia. We are walking distance to the casino, and 2.2-mile from Walmart and various dining options. For those looking to explore Nashville, we are just an hour away. Please take note of our pet fee and additional guest fee detailed below.

The living room features a comfortable sofa and loveseat, accented with decorative pillows. A stylish coffee table is centered on a patterned area rug. Light streams through large windows covered with sheer curtains, and wall art complements the welcoming atmosphere.

4.95 out of 5 average rating, 265 reviews

Entire 3BR House close to APSU Ft Campbell &Casino

Entire 3 bedroom house , located just minutes from Austin Peay, Fort Campbell, and the Oak Grove Casino. This home has a beautiful open floor plan with a kitchen, dining area, and living room for everyone to enjoy together. Go out into the spacious backyard which also includes a swing set for the kids! Enjoy this beautiful home and all that it has to offer. ✔3 Comfy Bedrooms ✔Fully Equipped Kitchen ✔Large Backyard ✔Smart TV ✔Washer/Dryer ✔High-Speed Wi-Fi ✔1 car garage & driveway

4.95 out of 5 average rating, 607 reviews

Tiny home in Clarksville

Tiny Town's Tiny Ship

Our tiny ship is a tiny house with a flair for the nautical. Our Tiny Ship is stranded between a few homes and tucked away from sight. She has everything you need as you visit our fair city,. We have a wet bathroom with a 6 gal hot water tank (10 min continuous hot water. And a map to help ye on your travels! ⚓️⚓️ We welcome one pet, but they must be crated when left alone, and a $15 pet fee. Also, it is located on a main road with neighbors, so complete silence is impossible.

The living room features a light blue wall, two comfortable sofas, and a patterned area rug. A coffee table sits center, with a ceiling fan above providing airflow. A window allows natural light, while a dining area is visible through the open doorway.

4.94 out of 5 average rating, 161 reviews

Paw-fect for pet lovers & thrill seekers

Whatever brings you to Oak Grove KY or Clarksville TN and surrounding areas, this renovated three bedroom house is sure to make you feel at home, away from home, in all the right ways. Paw-fect space is perfectly equipped for you to enjoy a home suitable for all groups. Book your next trip with confidence and learn why so many guests have ranked this house the premier place to stay in Oak Grove KY. Message us for more information about discounted extended stays.

The exterior of the house is illuminated by soft lighting along the pathway, enhancing the welcoming entrance. An American flag is displayed, and the covered porch features a welcoming door. The well-maintained lawn is bordered by neatly arranged flowers.

4.84 out of 5 average rating, 161 reviews

Beautiful 3-bedroom house

Cozy and family-friendly 3-bedroom home in Oak Grove, KY. Enjoy high-speed Wi-Fi, air conditioning, a fully equipped kitchen, laundry area, outdoor grill, and everything needed for a comfortable stay. Located less than 10 minutes from Oak Grove Racing & Gaming and Fort Campbell Military Base, 20 minutes from downtown Clarksville, TN, and under 1 hour from Nashville. Perfect for families, business travelers, and long or short stays.

A living room is presented with a light-colored ceiling fan above. A grey sofa and a chair are arranged around a coffee table, with a patterned rug beneath. A television stands on a low media unit, and large windows are framed by navy curtains, allowing natural light to enter.

4.87 out of 5 average rating, 224 reviews

Spacious | 4BR Boho | Family + Pet Friendly

Bring the whole family to this great place with lots of room for fun. This stylish 4 bedroom / 2.5 bath home is located in the Liberty Park neighborhod of Woodlawn. Just a few miles from Fort Campbell (Gate 10). This quiet, family-oriented community is conveniently close to both Clarksville and nearby recreational hot spots. The home is a full time Air-Bnb that is professionally cleaned and stocked with kitchen and bath essentials.

A spacious living area features a large sectional sofa, a round coffee table, and a wooden TV stand. Natural light enters through large windows, illuminating the soft color palette. A decorative wall art piece and a staircase add to the modern design.

4.89 out of 5 average rating, 114 reviews

Stunning 5 Bed 2.5 Bath

Beautifully renovated 5 bedroom 2.5 bathroom home located in the heart of Clarksville! Close to all of the amenities of Fort Campbell Blvd, Wilma Rudolph Blvd, and Tiny Town Rd. Easily could sleep 10 or more! This home is pet friendly, with stylish furnishings and super comfortable beds. Serene patio space with market lights that backs to trees. Air hockey and foosball table in the garage for your enjoyment!

A spacious living room is filled with natural light from several windows. A long, comfortable sectional couch and a central coffee table offer ample seating. Two wicker chairs are positioned nearby, and a vibrant area rug adds a touch of color to the wood floor.

4.88 out of 5 average rating, 141 reviews

Great for the whole family!

Kick back and relax in this calm, stylish space. With 2 living rooms & an outdoor living area, there will be plenty of space for you to spread out and get comfy. New 65" Smart TV & long comfy couch - perfect for movie nights with the whole group! Local Attractions- 5 miles from Downtown Clarksville (~10min) 15 miles from Fort Campbell (~30min) 45 miles from Downtown Nashville (~45min)

A spacious living area is highlighted by a cozy seating arrangement with a large sofa and throw blanket. Natural light filters through the sheer curtains, illuminating the space. A mounted TV is positioned above a modern fireplace, and a dining table is visible in the background near the kitchen.

4.96 out of 5 average rating, 138 reviews

Beautiful & Airy Retreat with Lots of Character

Welcome to your spacious and airy retreat at Russet Ridge! Nestled in a prime location just minutes from Wilma Rudolph Boulevard, this charming three-bedroom, two-bath home offers the perfect blend of comfort, convenience, and style. Whether you’re in town for a relaxing getaway, a business trip, or just exploring the area, this home provides the ideal setting for any stay.

Tiny home in Hopkinsville

The image captures a serene outdoor sunset view framed by large glass doors. Two modern chairs are positioned on a wooden deck, overlooking a grassy area and trees silhouetted against a vibrant sky filled with shades of orange and purple.

5 out of 5 average rating, 111 reviews

Peaceful, Romantic Getaway in Nature

Enjoy the lovely setting of this romantic spot in nature. Conveniently located less than ten minutes from downtown Hopkinsville in a private area with great views of the outdoors and wildlife. Guests can enjoy our hiking trails during their stay. Handicap accessible: walk-in shower 5x5 ft, all doorways >32 inches, no steps. Well-behaved pets allowed with pre-approval.

Popular amenities for Oak Grove family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.94 out of 5 average rating, 318 reviews

The cabin features a welcoming front porch with wooden railings and steps leading up to a central door with a rustic design. Natural wood elements complement the structure, blending with the surrounding greenery for an inviting appearance.

Cabin in Hopkinsville

1 Bedroom, 1 Bathroom Cozy Cabin with Hot Tub.

A spacious outdoor area is enclosed within a wooden pergola, featuring comfortable seating arranged around a central coffee table. A hot tub is positioned nearby, with textured flooring and greenery suggesting a serene setting for relaxation.

4.86 out of 5 average rating, 236 reviews

Private Yard: Hot Tub/B-Ball Court/X-Box/Fire Pit!

4.94 out of 5 average rating, 392 reviews

A unique structure resembling a boat stands on a grassy hillside, surrounded by trees. A wooden deck encircles the building, featuring round windows along its exterior. The rustic design and red metal roof complement the natural landscape.

Boat in Springfield

Sheet

A cozy living room features a deep brown leather sofa paired with a bright orange chair. Light streams in through large windows, framed by soft white curtains. A wooden coffee table holds decorative items, while wall art depicting butterflies is displayed above the sofa.

4.86 out of 5 average rating, 166 reviews

Eclectic Getaway with Hot tub and Hiking Trails

4.9 out of 5 average rating, 437 reviews

A spacious sleeping area features a large bed adorned with decorative pillows. The headboard is complemented by a green floral wall, while warm lamp lighting creates a calming ambiance. A cozy seating area and an intricately designed cabinet are also visible, adding a touch of charm.

Barn in Clarksville

Tiny Barn on a Farm Hot Tub 45 min to Nashville

4.98 out of 5 average rating, 295 reviews

A serene lakeside dock is visible, surrounded by mist and tranquil waters. Two wooden chairs and a small table are placed on the deck, offering a peaceful spot to relax and appreciate the natural beauty. Lush vegetation borders the lake, enhancing the secluded atmosphere.

Guest suite in Nashville

Lake House Retreat

4.97 out of 5 average rating, 242 reviews

A two-story white manor features large windows and a welcoming front porch, surrounded by manicured shrubs and a grassy lawn. The structure is set against a backdrop of wooded hills, conveying a sense of privacy and tranquility.

Home in Joelton

White Oaks Inn Country manor in rural neighborhood

4.97 out of 5 average rating, 153 reviews

The treehouse is illuminated by soft outdoor lights, highlighting its wooden structure and welcoming design. A gently curving walkway leads to the entrance, surrounded by tall trees and a glimpse of Lake Malone visible in the background.

Treehouse in Lewisburg

Treehouse with HOT TUB!(Lake Malone)

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 108 reviews

A cozy living space features a stone fireplace with a flat-screen television mounted above. A light-colored armchair and a decorative pouf complement the room's soft neutral palette. Natural light enters through large windows dressed with sheer curtains, enhancing the inviting ambiance.

Home in Elkton

Elkton Family House

4.9 out of 5 average rating, 29 reviews

Little Sorrento

4.96 out of 5 average rating, 25 reviews

Home in Hopkinsville

Cozy quaint cottage 3 bedrooms

A single-family home is depicted with a brick facade and a neatly maintained lawn. The entrance features a set of stairs leading up to the front door, flanked by two large windows. A two-car garage is visible on the right side.

4.68 out of 5 average rating, 22 reviews

The Rosy Outlook

The front of the farmhouse features a spacious porch with rocking chairs, surrounded by greenery. The white siding contrasts with the dark roof, while large trees provide shade. A gently sloping yard leads toward an open space, creating a peaceful outdoor environment.

4.97 out of 5 average rating, 70 reviews

The Boxwood

A dining area features a round wooden table surrounded by four black chairs. A decorative wall greeting is visible, along with large windows allowing natural light. A television is positioned next to the table, and a standing snack dispenser adds a functional touch.

4.96 out of 5 average rating, 111 reviews

Renovated 2bed 1bath! Near Ft. Campbell

Apartment in Hopkinsville

A two-story brick apartment building is positioned on a grassy lot, surrounded by trees. The facade features multiple windows with dark shutters and a central entrance highlighted by a blue door. Clear blue skies create a bright backdrop for the exterior.

4.9 out of 5 average rating, 31 reviews

Apt 3 - Furnished 2 bdr 2nd floor Apartment

A single-story home is presented, featuring a light brown exterior and a dark brown garage door. A well-maintained lawn with green grass is visible in the front yard, accompanied by a few small shrubs. A welcoming entrance is marked by a wooden door and decorative sidelights.

5 out of 5 average rating, 29 reviews

The Gate 4 Getaway

Family-friendly home rentals with a pool

A modern kitchen features dark cabinetry complemented by light granite countertops. Stainless steel appliances, including a refrigerator and microwave, are visible. Two pendant lights hang above the kitchen island, and a sink is positioned between the counter space. A decorative sign is displayed on the backsplash.

4.89 out of 5 average rating, 110 reviews

Beautiful Townhome with Pool

5 out of 5 average rating, 30 reviews

Rally Point Inn: pool, gym, hot tub, arcade

A comfortable living room area is featured, with two light-colored sofas adorned with various patterned throw pillows. A square ottoman is positioned in the center, while a decorative area rug adds texture to the floor. A wall-mounted artwork enhances the space.

4.99 out of 5 average rating, 87 reviews

Rustic Retreat

4.98 out of 5 average rating, 90 reviews

A welcoming living area features a purple sofa and a light-colored armchair, positioned on a multi-colored area rug. A simple bookshelf stands in the corner, while a small table holds a potted plant. The grey mountain mural adds depth to the room.

Townhouse in Clarksville

Blue Ridge Townhome

5 out of 5 average rating, 3 reviews

Condo in Clarksville

Cottage w/ Community Pool (0.8 Miles from Winery)

4.98 out of 5 average rating, 112 reviews

An outdoor fire pit area is framed by a wooden structure with string lights overhead, casting a warm glow. Two swings hang from the structure, while the surrounding green space adds to the inviting atmosphere. The home is visible in the background.

Home in Cheatham County

Solitude of Music City- Heated Pool-HotTub-FirePit

4.97 out of 5 average rating, 178 reviews

A two-story brick home is showcased against a clear blue sky. The exterior features evenly spaced windows with dark shutters and a welcoming front staircase leading to the entrance. Lush green grass surrounds the house, enhancing its inviting curb appeal.

Home in Nashville

Home Away from Home (w/Theater Room, Pool & Spa)

A bright living area is displayed with a comfortable orange sofa and an accent chair. A wooden coffee table sits in the center, complemented by a decorative rug. Natural light enters through windows, highlighting a piece of art featuring a cow on the wall.