Holiday rentals in Southside

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Top-rated holiday rentals in Southside

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Guest favourite
The living and dining area features a comfortable couch, a dining table set for four, and a decorative rug. Natural light is provided by sliding glass doors leading to a balcony. Soft blue and neutral tones create a calming ambiance.
Apartment in Clarksville
4.89 out of 5 average rating, 143 reviews

The Lofts of Downtown (540 N 2nd St, #211)

The Lofts of Downtown, Hosted by Byers & Harvey. Our stylish condos are perfect for travelers looking for a convenient and comfortable place to stay. Take a walk to Shelby Trio and sightsee on their rooftop bar. Enjoy our spacious living area with a full kitchen and comfortable sleeping accommodations. Enjoy high-speed internet for working remote or stream your favorite shows. Whether you're here for a weekend getaway or a long-term stay, we have everything you'll need for a memorable experience

Top guest favourite
A studio loft features charming brick walls and bright windows that allow natural light to fill the space. A spacious bed is positioned beside a comfortable sectional sofa. A media console and decorative accents enhance the cozy atmosphere, creating a welcoming environment.
Loft in Clarksville
4.97 out of 5 average rating, 183 reviews

A cozy studio apartment downtown Clarksville

The allée des fraises loft is a studio loft inspired by my stay in Paris and London, located on the second floor of an historic 1890’s building. The charming brick walls and rustic aesthetics add character to this bright space. Perfect for a couple’s getaway or a solo traveler in town for work. Walking distance to coffee shops, restaurants, local cafes, boutiques, breweries and more. Near Austin Peay State University, Fort Campbell and less than hour from Nashville. A parking pass is provided.

Guest favourite
A cozy sleeping area is present with a spacious bed adorned with soft, white sheets and a patterned blanket. A small bedside table holds two glasses and a decorative antler. A decorative pillow adds a touch of warmth, while a plant sits next to a cup on the table.
Guest suite in Madison
4.96 out of 5 average rating, 263 reviews

Luxe jetted tub, fire pit, king bed! •The Firefly•

Only 11 miles to Broadway, and 10-15 minutes to the Opry and East Nashville! Get away from the city buzz in our quiet neighborhood without compromising proximity to downtown. This basement studio features a full kitchen, jetted spa tub, KING bed, and a patio with outdoor seating and a fire pit. Please note that this is the downstairs of our home and there are stairs up to a locked door which we have put a curtain over. We do have a baby and a dog upstairs, so minor overhead noise is possible!

Superhost
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.
Home in Clarksville
4.92 out of 5 average rating, 185 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.

Top guest favourite
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
4.99 out of 5 average rating, 111 reviews

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!

Top guest favourite
The front exterior of the home features a welcoming covered porch with a bench and decorative pillows. A flag is displayed prominently beside the entrance, and colorful rose bushes line the walkway, which leads to the door. The siding is light-colored, complemented by dark shutters.
Home in Clarksville
4.92 out of 5 average rating, 369 reviews

Fort Campbell Retreat w/ Tesla Charger

3 bedrooms and 1.5 bathrooms. Master has king size bed, walk-in closet and own half bath. Spare room has double bed and walk-in closet. Minutes from Fort Campbell, Downtown Clarksville and Governor's Square Mall. 45 Min from Nashville Airport. Neighborhood Walmart Marketplace within walking distance. Brand new washer, dryer and refrigerator. High-speed Wi-Fi, big screen TVs w/ Roku and Nespresso coffee. Relaxing patio deck backing up to a woodland paradise! 50amp Tesla Wall Charger.

Top guest favourite
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.
Flat in Clarksville
4.99 out of 5 average rating, 193 reviews

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!

Top guest favourite
A spacious living area features comfortable seating arrangements with a gray sofa and a patterned blue armchair. Large windows provide views of the river, while light wood flooring enhances the airy atmosphere. Two ceiling fans help maintain a comfortable environment.
Home in Ashland City
4.91 out of 5 average rating, 160 reviews

Spacious 4-BR Tranquil Waterfront Retreat

Forget your worries in this spacious and serene space situated directly on the Cumberland river. This exquisitely designed and remodeled home offers sophistication and elegance while providing the ability to relax and unwind from the bustling city. Plenty of space for the entire family to enjoy some quality time together. Located close enough to Nashville that you can still enjoy a night out in the city or stay local and enjoy dinner at the marina or drinks at the local distillery.

Top guest favourite
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
4.95 out of 5 average rating, 376 reviews

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.

Top guest favourite
The exterior of a townhouse-style condo is shown, featuring a well-maintained entryway with a porch. Lush green shrubs border the walkway, which leads to the front doors. The roofline is varied, and the windows provide natural light to the inside.
Home in Clarksville
4.94 out of 5 average rating, 100 reviews

The Winery

Enjoy a stylish winery-inspired experience at this centrally located condo! Full sized sectional to cozy up on and watch TV, a full kitchen to make you feel at home and complimentary coffee bar! Two bedrooms with comfy queen beds and full bathrooms attached to each. Nice sitting areas in front and in back to relax on. Close to shopping, dining, I-24 and Tennova. Minutes to Beachaven Winery, 5 minutes to the mall, 20 minutes to downtown Clarksville and 50 minutes to Nashville!

Guest favourite
Flat in Clarksville
4.9 out of 5 average rating, 131 reviews

Serene private new construction walk out apartment

Beautiful 1 bed 1 bath apartment tucked into the woods in Cumberland Heights. Enjoy a private getaway but still convenient access to all that Clarksville has to offer. Close to Austin Peay State University, 10 minutes from downtown and 30 minutes from Fort Campbell. The Space: Comfortable queen bed with full bath (shower only-no tub). Private entrance to walkout basement apartment. No access to main house from apartment. Full kitchen with coffee provided.

Top guest favourite
The exterior of a charming cabin showcases dark wood siding and large windows adorned with stained glass. A spacious wooden deck wraps around the structure, providing access to multiple outdoor areas. Lush greenery surrounds the property, enhancing the secluded atmosphere.
Treehouse in Kingston Springs
4.94 out of 5 average rating, 162 reviews

The Treehouse Cabin

Beautiful, secluded property 20 minutes from downtown Nashville. Feels like a treehouse! Guests have access to entire property. The apartment has a kitchen, bed, bathroom, and fireplace. There is a large living room with a sitting area, pub table, big screened TV, and couches. To top it all off, guests have a screened-in gazebo with a gas fire pit. You can not beat the serenity or the views! Only 5 minutes to local stores & restaurants.

Popular amenities for Southside holiday rentals

  1. Airbnb
  2. United States
  3. Tennessee
  4. Montgomery County
  5. Southside