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Holiday houses in Olive Branch

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Top-rated holiday rentals in Olive Branch

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

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Top Guest favourite
The cabin's welcoming entrance features a wooden porch supported by sturdy beams. Two rocking chairs sit on the porch, surrounded by greenery and stone accents. A red door and a large window enhance the cabin's rustic charm, while the natural setting invites relaxation.
Cabin in Cobden
4.99 out of 5 average rating, 147 reviews

Pop’s Country Cabin

Pop’s Country Cabin is a small remote cabin that sits 1/2mile off the road above a 5 acre lake on 77 acres of private land. The view from the front porch is amazing! You can sit, unwind, and watch the wildlife with a distant view of Bald Knob Cross. The cabin sits in the heart of Shawnee National Forrest and the Southern IL wine trail. You can enjoy the fire pit while watching the stars, with no distractions from neighbors, traffic, or lights. You can enjoy catch & release fishing from the bank

Top Guest favourite
The exterior of a cozy wooden cabin is displayed, featuring a steeply pitched roof and large front windows. Two comfortable adirondack chairs are positioned nearby on a gravel path, alongside a small fire pit. Lush greenery surrounds the cabin, enhancing its serene setting.
Tiny home in Makanda
4.9 out of 5 average rating, 113 reviews

Pet-Friendly Tiny Cabin* Near Blue Sky*Shawnee

Après Vine Tiny Cabin is your escape to a serene minimalist cabin in Shawnee National Forest! Just 5 min to Blue Sky Vineyard, hiking, zip lines, and I-57, this retreat blends adventure and tranquility. Relax by the fire pit, take in sunsets, rolling pastures, and woodlands. No Wi-Fi or TV ensures a true digital detox. Friendly livestock guardian dogs may greet you. **Pet-Friendly: Bring your furry friend—just add them to your reservation! Perfect for nature lovers seeking a peaceful getaway.

Top Guest favourite
An exterior view of the entrance features a welcoming white door framed by black accents. A small staircase leads up to the door, complemented by a light fixture. A vehicle is parked near the entrance, with a tree and a fenced area visible in the background.
Guest suite in Cape Girardeau
4.98 out of 5 average rating, 168 reviews

MAINSTAY CAPE [downtown]

Nestled in the heart of the Downtown Historic District, this suite is centrally located as a prime destination for any and all travelers alike. With parking available, this space offers a unique & trendy “midwest boho” vibe. ~WALKABLE~ Our studio is 1 block from the bustling Southeast Missouri State University, 1 block from the gorgeous Capaha Park, and 2 blocks from Mercy Hospital. If you are interested in night life, this space is simply a 5-10 minute walk to all DT bars and restaurants.

Top Guest favourite
A spacious living area features large windows allowing natural light to fill the space. A comfortable grey sofa is paired with a unique coffee table, while stylish dining chairs surround a white table. The kitchen area includes modern appliances and cabinetry.
Apartment in Cape Girardeau
4.95 out of 5 average rating, 272 reviews

Brand new 2 bedroom unit right in downtown Cape.

This special place is close to everything, making it easy to plan your visit. Walking distance to restaurants, the river and nightlife. Property includes wifi, full kitchen, laundry, deck and private parking for one. One king bed room and a twin bed room in addition to a roll out twin bed along with a 60 inch smart television. Dog bed and bowls included along with board games! Property is conveniently located across the street from "The Bar" the famous spot from the movie "Gone Girl" .

Guest favourite
The kitchen area features a central island with two sleek stools, complemented by a modern black vent hood. Stainless steel appliances, including a refrigerator and stove, are positioned against a marble countertop. Decorative plants and tableware enhance the stylish design of the space.
Loft in Cape Girardeau
4.93 out of 5 average rating, 110 reviews

Riverwalk Loft 1

If you are looking for something right in the middle of the excitement, book now! This is your place. Our lofts are right in the heart of Downtown. In walking distance to breweries, casinos, and shopping galore.Our building is directly in front of the Mississippi River entrance. Walk around the corner either to get an ice cream for a late night snack. Beds are super comfortable but downtown isn’t the quiet part of town. The train runs periodically. You will have the typical night life noise.

Top Guest favourite
A modern dome structure features large glass panels creating a bright and inviting environment. Surrounded by lush greenery, the architecture harmonizes with nature. A wooden deck with seating is visible in front, offering a space for relaxation and outdoor enjoyment.
Dome in Cobden
5 out of 5 average rating, 127 reviews

The Dome At Blueberry Hill

Escape to The Dome at Blueberry Hill, where comfort meets nature for a truly unforgettable glamping experience. Set on two private acres along the scenic Shawnee Hills Wine Trail and minutes from the charming village of Cobden- you’ll enjoy peaceful seclusion with easy access to local charm. The fully insulated dome offers cozy, climate-controlled comfort year-round. Sip wine under the stars or unwind in style indoors. Make lasting memories at The Dome- your luxury glamping retreat awaits.

Top Guest favourite
A red barn with a peaked roof is set against a lush green landscape, reflecting softly in a calm pond nearby. Tall grasses frame the water’s edge, while trees provide a natural backdrop under a partly cloudy sky.
Cabin in Dongola
5 out of 5 average rating, 103 reviews

Charming Cabin Overlooking 5 Acre Lake

This cozy, newly remodeled, and inviting cabin offers you a relaxing, serene, and tranquil setting. During your stay you will see nature at its finest. Enjoy a drink on the large deck overlooking the picturesque landscape as well as the lake. If you enjoy fishing then this stocked lake is the place for you. Feel free to fish on the bank or the dock. This cabin is part of the original homestead that was established in 1855 by Valentine Kimber. Located close to wine trails and interstate 57.

Top Guest favourite
The custom-built treehouse is elevated on stilts, surrounded by greenery. A spacious deck features a railing, offering access to the entrance. Steps lead to the ground below, while large glass doors enhance the connection to nature.
Treehouse in Cape Girardeau
4.99 out of 5 average rating, 171 reviews

Twisted Sassafras Treehouse

A custom-built treehouse located on 10 acres with a water view that you can take in from the hot tub on the deck! It is nestled high in the trees and is the perfect romantic getaway for two! Feel like you are away from it all without being away from it all! This treehouse is located on a county road just minutes from Cape Girardeau. Enjoy catch and release fishing on site, local wineries, shopping in historic downtown Cape Girardeau, local restaurants, gambling, historical sites & more!

Top Guest favourite
A cozy sitting area is surrounded by wooden walls, featuring a large window that offers views of the forest. A red chair stands next to a small side table, while a gray couch is positioned against the wall. Decorative art pieces adorn the space.
Tiny home in Cobden
4.95 out of 5 average rating, 120 reviews

Tiny House of Paul - Center For Lost Arts

Perfect if you're working or spending time exploring Southern Illinois. Great discount for longer stays. Tiny House of Paul house has a cozy & spacious feel. A large west-facing window looks out onto the forest. Windows in the loft open to tree tops & stars. Private inside. Centrally located on the property of Center For Lost Arts near Cobden, Illinois. Wander the trails at the end of a work day, or relax on the deck after hiking or exploring. Enjoy your time in Southernmost Illinois.

Guest favourite
A spacious roof deck is highlighted, featuring a wooden surface and metal railing. Two woven chairs and a small table are positioned to allow for relaxing moments while enjoying expansive views of the river and surrounding greenery.
Apartment in Cape Girardeau
4.96 out of 5 average rating, 158 reviews

Downtown Penthouse w/ Amazing River View!

AMAZING RIVERVIEW Plus Close to Downtown Cape? Our Airbnb is the best place to be! Relax in our Roof Deck after going around downtown and ENJOY THE VIEW. Located in a safe and quiet neighborhood plus it is WALKING DISTANCE from everything! It features a roof deck with (by far) the best view in Cape, enough space for six to sleep (two queen beds and two couches), one off street parking spot and a building with secure entry. Plus we just live across the street if you need anything.

Top Guest favourite
A modern farmhouse is depicted at sunset, featuring a welcoming entrance with a covered porch. A stone pathway leads to the front door, bordered by a grassy lawn that extends to fields and trees in the background.
Barn in Cape Girardeau
4.94 out of 5 average rating, 229 reviews

Under the Stars - Farmhouse

Enjoy the tranquility of this modern farmhouse charmer! Custom built minutes from downtown Cape. Relax outside around the fire pit, roast marshmallows and watch the sunset. Finish the night with a long soak in the hot tub. Start the morning on the front porch rocking chairs and take in a sunrise. Open concept, fully equipped kitchen, 3 Bd. including King master/full bath, 2 Queens with full guest bath. Near Trail of Tears and walking distance to classic dive bar/burger joint

Top Guest favourite
A cozy living space features exposed brick walls complemented by a patterned area rug. Two armchairs provide comfortable seating, one in a checked pattern and the other a textured fabric. A window is adorned with sheer and geometric-patterned curtains, allowing natural light to illuminate the room.
Guesthouse in Cape Girardeau
4.94 out of 5 average rating, 550 reviews

Downtown Guesthouse- Romantic Getaway

The guesthouse seamlessly blends modern amenities with historic charm in a cozy, compact space. The antique claw foot tub/shower combo offers a charming, yet snug, spot for a relaxing soak—true to its historic roots, the bathroom could be best described as a quaint water closet. After a day of exploring unwind in the patio. Play a favorite record, and savor your coffee while daydreaming about new experiences. Despite its small size, it provides all the modern comforts you need.

Popular amenities for Olive Branch holiday rentals