Vacation rentals in Southside

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Southside

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

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.

4.92 out of 5 average rating, 118 reviews

Guest favorite

A hot tub is positioned outside, with its water shimmering under a soft blue light. Large windows display the interior, showcasing a colorful seating area and decorative plants, creating a harmonious connection between indoor and outdoor relaxation spaces.

Home in Clarksville

Elegant Entertainment Home The SPOT + HOT TUB

Top Reasons why you’ll love our home! We’re located in a very safe area just minutes away from many of the main attractions of Clarksville. You’ll reside in a 2,300 sqft house w/ 3 bedrooms furnished with insanely comfortable beds w 2 full bathrooms and 2 full kitchens for your convenience & space. The home sits beautifully on the edge of some of Tennessee's most beautiful trees and is also frequently visited by deer and other harmless wildlife. Grab some coffee and enjoy the morning nature view

4.9 out of 5 average rating, 218 reviews

Superhost

Cabin in White Bluff

Log Cabin Retreat w/ Private Trails and Party Barn

Escape to a secluded log cabin just 32 miles from downtown Nashville. Set on 18 private acres, this whimsical retreat offers the perfect balance of convenience and tranquility -- close enough to the energy of the city, yet far enough to unwind. Ideal for those seeking both adventure and relaxation. Enjoy the private hiking trails, nearby outdoor activities, or spend a night out in Nashville before returning to your peaceful retreat. Rustic, cozy, and full of true character. *Party barn included

5.0 out of 5 average rating, 4 reviews

Top guest favorite

A tranquil sunset sky is displayed with colorful clouds in shades of pink and blue. The tiny house is seen on the right, featuring a porch and a small wooden privacy screen. The surrounding area is lush with green trees and an expansive grassy space.

Home in Southside

Paradise Hill Tiny House

Relax in this calm, stylish space. Come enjoy your stay at our small, quaint, inviting tiny house located in a peaceful country setting. Property is very close to the Historic Southside Market, Historic Collinsville and a short drive to beautiful Charlotte, TN where you can shop their unique variety of farm to table and craft stores. Only 14 miles to Clarksville, TN, 26 miles to Dickson, TN and 42 miles to Nashville! Come relax in the country and soak in the beauty and peacefulness of it all!

4.99 out of 5 average rating, 136 reviews

Top guest favorite

A cozy living room features two soft sofas arranged around a round coffee table. A stone fireplace serves as a focal point, while large windows allow natural light and offer views of the surrounding landscape. A dining table with white chairs completes the inviting space.

Cabin in Pleasant View

Storybook Cabin Near Nashville

Enjoy a secluded retreat at The Feathered Nest, a charming log cabin just 20 minutes shy from Downtown Nashville. Built in 1979 and situated on 15 acres of land, this traditional wood cabin provides a private oasis with sprawling views of green pastures. Surround yourself with the quaint country atmosphere without being too distant from the center of Nashville. Access to grocery stores and lovely local shops are just a 5-minute drive away. A haven for those who are seeking quiet solitude.

5.0 out of 5 average rating, 112 reviews

Top guest favorite

A contemporary living room is highlighted by a large mirror and stylish light fixture. A comfortable gray sofa with colorful throw pillows is positioned near a wooden coffee table. A vibrant area rug complements the hardwood floor, while a flat-screen television is mounted on the wall.

Apartment in Clarksville

2 Bedroom Hidden Gem, Downtown Clarksville

Kick back and relax in this calm, stylish space. This is a charming home nestled in the heart of Clarksville! This cozy Airbnb is the perfect choice for your stay in the vibrant city of Clarksville. As you step inside, you'll be greeted by a warm and inviting atmosphere. The living room is tastefully furnished, providing a comfortable space for relaxation and entertainment. Whether you're visiting for business or pleasure, this is the perfect home away from home. Book your stay today!

4.99 out of 5 average rating, 238 reviews

Top guest favorite

A cozy cabin is nestled among lush greenery, partially obscured by mature trees. A gravel path leads to the entrance, which is flanked by wooden accents. A small outdoor seating area is visible, enhancing the connection to the serene natural surroundings.

Cabin in Chapmansboro

White Duck

Keep it simple at this peaceful and centrally-located cabin minutes from Interstate 24. Twenty minutes from Clarksville, APSU and nearby Fort Campbell KY to the north and thirty minutes from downtown Nashville and all it has to offer to the south. The quiet woodsy setting and comfortable interior of White Duck provide a restful transition from a day of sightseeing or an exciting football or hockey game. **There is a $50 pet fee** Please include your pet during the booking process.

4.96 out of 5 average rating, 450 reviews

Top guest favorite

A charming treehouse is nestled among tall trees, featuring earthy wooden tones and a rustic design. Soft outdoor lighting creates a cozy ambiance, while a path made of stones leads to the entrance. The treehouse is elevated, providing a unique vantage point into the surrounding nature.

Treehouse in Greenbrier

Nashville Luxury Dream Treehouse +Spa

This beautifully designed and luxurious treehouse sits on a ridge overlooking our creek. With only a 25min drive to downtown Nashville, Grand Ole Opry, you are tucked away amidst the towering hardwoods-away from the city noise. With careful attention to detail, the treehouse decor and design is meticulously curated to create an atmosphere of rest and beauty. This space is ideal for a couple, but can sleep four (twin beds in the loft). Parties are not permitted on the premises.

4.97 out of 5 average rating, 352 reviews

Top guest favorite

A single-story brick home is positioned on a gently sloping lawn, surrounded by greenery. A concrete pathway leads to the front entrance, flanked by small shrubs. Large windows provide ample natural light, contributing to a welcoming appearance from the peaceful neighborhood.

Home in Clarksville

Henrietta House: Quiet Comfort with Fenced Yard

Henrietta House is a recently renovated home on a quiet, leafy street in an established neighborhood. Perfect for families or anyone looking for a fun and relaxing getaway, the home has a full kitchen and a fenced back yard. We are a 15 minute drive to APSU and downtown Clarksville; 5 minutes from Exit 11 on I-24, 5 minutes to Publix and Walmart, 30-40 minutes to Ft. Campbell, 45 minutes to downtown Nashville. Driveway or garage parking. Dogs welcome. No added-on cleaning fee.

4.98 out of 5 average rating, 129 reviews

Top guest favorite

The Bridge House is seen suspended over a serene creek, framed by lush greenery. A calm water surface reflects the building and surrounding foliage. A gray dog stands on a rock in the foreground, appearing to enjoy the natural setting.

Place to stay in Ashland City

Bridge House over Blue Springs Creek

Magical in all seasons! Soothe your soul with an unforgettable escape, surrounded by nature and suspended twenty feet above a babbling brook! Listen to the rushing water and the bamboo whispering in the breeze, take in a sunset, or wade in the creek below. We hope you’ll enjoy this unique covered bridge conversion, expanding from bank to bank with a 50-foot front deck. Breakfast provided the first day includes fresh fruit, a half dozen eggs, and muffins, coffee and tea.

4.97 out of 5 average rating, 436 reviews

Guest favorite

The outdoor space features a well-lit area with a hot tub, a wooden deck, and a swing set. Surrounding greenery adds to the natural setting, while a cozy structure is visible to the right, and a spacious lawn extends to the horizon under a colorful sky.

Barn in Pleasant View

*Private 2 Acres!* | Hot Tub | 20 Min to Nash!

Imagine sipping your wine in the hot tub as the sun sets over the rustic Tennessee Tobacco barn on the horizon. Imagine enjoying 2 acres of the country all to yourself, then popping in your car and hitting Broadway in 25 min. Imagine having a private retreat to enjoy quality time with your significant other just outside the city. If you want a retreat that is convenient to the city, the Guest Barn is for you!

4.96 out of 5 average rating, 100 reviews

Guest favorite

Home in Clarksville

The Horse Haven at Liberty Star Farms

The Horse Haven | 3BR Family Retreat w/ Fire Pit & Kids Play Area Hosted by Byers & Harvey, this rustic 3-bedroom, 2-bath getaway features an open-concept layout, spacious living areas, and family-friendly amenities. Enjoy the outdoor fire pit, children’s play structure, and dedicated play area—perfect for families, group stays, and relaxing retreats. Comfortable, inviting, and designed for connection.

5.0 out of 5 average rating, 8 reviews