
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.

Cape Charm: 3 BR Close to SEMO & Mercy! CLEAN!
Cape Charm is a "charming" 3 BR home in a safe, quiet neighborhood perfectly located next to SEMO, Mercy Hospital, Capaha Park & the historic district - all less than a 7 minute walk! Feel at home in a magnificently cute 3 bedroom home (w/king bed), fully equipped kitchen, living room, dining room, bathroom, & sun room. Free, fast WIFI, a smart TV in the living room & bedroom. It's centrally located to everything! We are experienced hosts with highly rated listings in Florida and Missouri.

Beautiful Historic Boulevard District Apartment
This beautiful, private upstairs apartment is located on a favorite street in Cape Girardeau’s Historic Boulevard District. It is walking distance to SEMO University, Capaha Park, and the downtown riverfront. Recently remodeled for laundry, spacious rooms offer private bedroom spaces and a cozy den for watching movies or reading. The kitchen is fully equipped with amenities. This quiet neighborhood setting even has a front porch swing and sitting area where you can enjoy your morning coffee.

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" .

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.

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.

RiverSide Barn Suite on the Mississippi River.
The barn suite is a beautiful 2 bedroom apartment overlooking the Mississippi River and housed in a unique barn with its own separate entrance. The deck views are spectacular and takes sitting and relaxing to a new level. Our wine place “The RiverHouse “ is within walking distance with the best worldwide wines and menu in the area. www.theriverhousewineplace.com We are 12 minutes from Cape Girardeau and serviced by Lyft & Car-Go. You May contact us by text or call and available at any time.

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!

Shawnee Hiking!Hot tub!Fire Pit!Wine Trail!
WELCOME TO LUXURY GLAMPING ON THE SHAWNEE WINE TRAIL OF BEAUTIFUL SOUTHERN ILLINOIS. You will be resting in an authentic oak timber cabin, built on the historical "Trail of Tears" in Union County - Anna, Illinois. This lodging offers the rustic appeal, a taste of Native America with the comforts of contemporary amenities including an outdoor hot tub all year long! *If you do not find your desired date available, be sure and check our twin cabin listing at AdamsRock Cabins, Cabin #2.

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

Cobden Retreat in the Woods
Eva’s Roost Retreat Cabin is located at Center For Lost Arts near Cobden, Illinois. Uniquely crafted rustic, zen-style cottage, designed to be close to the earth & nature. Extensive, curtainless windows facing the forest & pond allow for private views: sunrise, moonrise, forest & wildlife. Yoga mat, guitar & some art supplies. Personal outdoor space with firepit & comfy adirondack chairs. Entrance to wandering trails right outside your back door. Perfect place to retreat and renew.

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.

Updated Farmhouse w/ King Suite
Cozy updated farmhouse near the Southern Illinois Wine Trail and Shawnee National Forest. This warm and comfortable home blends minimalist style with rustic charm and features a King Suite, family-friendly amenities, and a peaceful, rural feel—yet it's just minutes from town. Only 24 minutes from SIU Carbondale, it’s perfect for campus visits, hunters visiting during the season, wine trail adventures, or a weekend close to nature!
Popular amenities for Olive Branch holiday rentals
Other great holiday rentals in Olive Branch

Large living space, 4 bedroom, outdoor fire pit

Historic home in Anna Jonesboro. Shawnee Forest.

The Brick Home

Enchanted Mermaid A-Frame | Creek | Pet Friendly

Edgewood Retreat

Dad's Place

Modern Cabin · Hot Tub & Shawnee Forest Access

The Cabin at Timber Creek
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