Vacation rentals in Simpson County

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Top-rated vacation rentals in Simpson County

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

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Guest favorite

A spacious bedroom is furnished with a large bed adorned with a patterned blue and white duvet. Natural light enters through two windows, framed by sheer curtains. A wooden dresser is positioned against one wall, complemented by a standing lamp and small nightstand.

Home in Harrisville

4.96 out of 5 average rating, 53 reviews

Country Retreat

Relax with the whole family at this peaceful place to stay. We offer 45 acres of woods with accessible trails, a perfect get away from the city life. Very beautifull and remote country setting and yet close enough to nearly restuarants, convenient stores and gas station. Spacious three- bedroom two-bathroom with fully equipped kitchen and laundry room. Bring your favorite fishing rods to fish in our pond for bass or bream or take a walk in the woods. Our chickens are ducks are people friendly.

Top guest favorite

Home in Mount Olive

5 out of 5 average rating, 7 reviews

The Magnolia House

Welcome to a slice of small-town Mississippi charm. Stay in a 125 year old historic Craftsman home on a peaceful Main Street boulevard, offering a spacious & unique blend of historic character and modern comfort. Start your mornings or end your evenings relaxing/dining on the expansive front porch or enjoying the Fire Pit. Inside, you’ll find period details blended with functional living area. Unwind after a long day with a luxurious soak in the vintage claw-footed tub.

Top guest favorite

A wooden staircase leads to a treehouse entrance, surrounded by lush ferns and tall trees. A welcome mat with a cheerful message is positioned at the base of the steps, and a sign labeled 'Owl Nest' is visible next to the door.

Treehouse in Mount Olive

4.99 out of 5 average rating, 135 reviews

A True Treehouse- Owls Nest @Pines and Pillows

Escape to our enchanting treehouse experience nestled in the heart of Mississippi's countryside. Experience rustic vibes among the treetops with cozy accommodations, breathtaking views, and comforting amenities. Perfect for romantic getaways or adventurous retreats, our unique rental offers a serene escape with a touch of whimsical charm. Book your stay now for an unforgettable experience in nature's embrace.

Guest favorite

Home in Magee

4.83 out of 5 average rating, 6 reviews

Raywood Manor

Enjoy this spacious home on 5 acres, featuring two inviting living rooms, a large family room, and plenty of comfortable spaces to relax and sleep. Have fun with the pool table and foosball table, or unwind on the full walk-around deck overlooking the fenced backyard. Located right in the middle of town, you’re within walking distance to Walmart while still enjoying peaceful, open surroundings.

A well-designed kitchen features wood paneling and a spacious island with a white marble countertop. Natural light fills the room through large windows. A green plant wall adds a touch of nature, while wooden dining chairs surround the island, creating a welcoming space for gatherings.

Cabin in Mendenhall

4.54 out of 5 average rating, 82 reviews

Hot Tub Vibes* Unlimited Wi-Fi *Rustic Cabin Reset

Escape to a cozy cabin in Mendenhall, MS with a hot tub & fireplace! Perfect for couples, families, and last-minute getaways. Fast WiFi + kitchen for extended stays. Weddings must be pre-approved — contact host for pricing & approval!