Vacation rentals in Osceola

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Top-rated vacation rentals in Osceola

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Guest favorite
A view of a spacious basement apartment overlooking a pond, set against a backdrop of green grass and a clear blue sky. A playset is visible beside the water, and a fence encloses a grassy area for added privacy.
Guest suite in Weldon
4.86 out of 5 average rating, 37 reviews

Pond-view Suites

Enjoy the farm atmosphere in Southern Iowa. Bring the whole family to our quiet, spacious, basement apartment overlooking our pond. Relax on the back patio while the kids enjoy the playset and sandbox. Or enjoy a picnic down by the pond with table, fire ring with grille and free firewood. As the sun sets, enjoy the unique night sounds that only come with a pond. Whether you use one bedroom or three, we rent to only one party; the living space and the bathroom is all yours, with private entrance.

Top guest favorite
The exterior of the house is visible, featuring light-colored siding and traditional shutters on the windows. A charming old wagon wheel is positioned in the foreground, alongside a leafy tree. The inviting front steps lead to the entrance of the home.
Home in Indianola
4.99 out of 5 average rating, 192 reviews

The Hen House

The wonderfully remodeled home based on 55 acres overlooking mature trees and a large pond. The house has 3 bedrooms and 1 1/2 baths. Laundry is available to use as well. Kitchen is fully stocked for your cooking enjoyment and a gas grill is offered as well to use. This house is perfect for families, small groups, or business trips. Situated just 20 minutes from Des Moines airport, and 25 minutes from downtown Des Moines, you will be able to experience the quiet and beautiful scenery to enjoy.

Top guest favorite
A tranquil scene along a serene pond features a wooden dock with views of mist rising from the water. A cozy mug and an open notebook rest on a wooden surface nearby, inviting relaxation and reflection in a picturesque natural setting.
Tiny home in Norwalk
4.98 out of 5 average rating, 130 reviews

Private *Fall Oasis* Waterfront Tiny House & Sauna

The true definition of rest & relaxation, this unique tiny house is situated on a three-acre pond suitable for catch and release fishing, kayaking, or stand up paddle boarding. Bring your gear and leave your worries behind. Built with special touches and details including stained glass windows and intricate woodwork, this tiny home boasts warmth throughout. Wake up to bird songs and coffee with the sunrise. After a day of fun, take a soak in the wood-burning sauna and relax by the campfire.

Top guest favorite
A quaint cottage features a covered porch with white rocking chairs and a red chair, surrounded by lush green foliage. The wooden deck is complemented by straw bales and a barbecue grill. The front door is framed by a simple sign, adding charm to the rustic setting.
Farm stay in Lacona
4.89 out of 5 average rating, 75 reviews

Mulberry Cottage Farm-Stay

Take it easy at this unique and tranquil getaway as you enjoy your favorite beverage while rocking on the front porch. Our sunsets are stellar and you will enjoy a pond view and hear the sounds of cattle in the pasture. For a rustic, glamping experience build a fire in the fire pit and have a hot dog roast with s’mores. Your quaint cottage will have farm fresh eggs, sour dough bread and mulberry preserves for breakfast. Enjoy birdwatching, fishing at the pond or help with the farm chores.

Top guest favorite
The exterior of a welcoming house is presented, featuring a covered porch with seating. A large front door is visible, along with a second-floor window above the porch. Lush green grass surrounds the home, framed by trees in the background.
Apartment in Winterset
4.94 out of 5 average rating, 369 reviews

The Suite Iowa Life

THE BEST VALUE IN WINTERSET Don’t spend your money on an impersonal hotel when you can stay at our “home away from home!”! This Suite is located on the main level of our home where we live and work. It is a PRIVATE, FULLY EQUIPPED APARTMENT, UNSHARED SPACE. Separate entrance. Pets allowed. Access to yard and beautiful country views. * NEW MATTRESS * November 2023 Large backyard, grill, fire pit, close to town & centrally located amongst the six bridges. PLEASE READ FULL DESCRIPTION.

Top guest favorite
An outdoor deck is shown with a wrought iron table surrounded by several chairs. A gas grill is situated nearby, while greenery from surrounding trees adds a natural backdrop. The doors leading into the cabin provide access to the interior.
Cabin in Leon
5 out of 5 average rating, 41 reviews

The Hobbit Hut

A-Frame cabin blends rustic charm with cozy comforts, offering a retreat for outdoor enthusiasts or those seeking a peaceful hideaway. Whether you're here for adventure, relaxation, or to reconnect with nature, we offer a one-of-a-kind experience that's both private and comfortable with easy access to Little River Lake and hunting grounds, making it the perfect base camp for your outdoor pursuits. "You can stay home and be comfortable, or you can step outside and have an adventure.

Top guest favorite
An inviting outdoor deck area features a wooden seating arrangement under a metal roof, adorned with string lights. A spacious couch offers comfort, while a long wooden table complements the rustic charm. Lush greenery and open space are visible in the background.
Cabin in Cumming
4.98 out of 5 average rating, 166 reviews

Iconic Iowa - A 1920 Built Country Cabin

This 1920 Log Cabin sits at the beginning of the Madison County covered bridges Scenic Byway and features 2 rural country acres of space and a wonderfully remodeled home with loads of character and style. Situated just 10 minutes south of the West Glen area of West Des Moines and 25 minutes from downtown Des Moines, you'll experience the quiet and beauty of rural Iowa while being close enough for shopping or to go out for a nice dinner or evening show. This is a great getaway.

Top guest favorite
An outdoor space features a saltwater spa adjacent to a circular seating area with Adirondack chairs gathered around a fire pit. Lush grass surrounds the area, and trees frame the view, creating a peaceful retreat in the countryside.
Home in Afton
4.99 out of 5 average rating, 148 reviews

The Country Oasis

The Country Oasis is the ideal destination for those seeking a serene retreat or a rejuvenating escape. This delightful vacation rental features 2 bedrooms and 2 bathrooms, making it perfect for your next getaway. With modern amenities and comforts such as a hot tub, fireplace, and various gathering spaces both indoors and out, The Country Oasis guarantees a memorable experience with friends and family. Come and enjoy the best of country living in southwest Iowa!

Top guest favorite
A wooden deck is showcased in this image, featuring a gentle incline with steps leading up. Potted flowers and hanging planters add a touch of greenery. Two lamp posts provide soft illumination, enhancing the welcoming entryway to the home.
Home in Leon
4.99 out of 5 average rating, 77 reviews

The Country Escape

Country setting located just 2 miles W of Leon and less than a mile from Little River Lake. This newly remodeled house features a spacious, full kitchen, dining area with a 10 person farmhouse table, living room with 3 full couches , one of which doubles as a queen size bed. There is a smart TV. Bedroom 1 and 2 have a queen bed, bedroom 3 has 2 queen beds. Spacious patio with dining furniture. There is a circle drive to accommodate boat/trailer parking.

Top guest favorite
A spacious living area features large windows allowing natural light to fill the room. Two dark leather sofas and a light-colored couch are arranged around a wooden coffee table. A flat-screen television and a decorative rug enhance the inviting atmosphere.
Loft in Chariton
4.89 out of 5 average rating, 253 reviews

Braden Place

Located on the North side of the Chariton square. Large windows looking towards the courthouse. Light and airy decor. Iron Horse restaurant for lunch or supper along with our friendly Mexican restaurant and The Porch coffee shop, and several more all within walking distance. Vision II movie theater is only 3 blocks away with first-run movies. Southern Iowa charm surrounds you in this pristine historical setting. Be our guest at Braden Place.

Top guest favorite
An outdoor space features two metal chairs positioned under a covered porch. The ceiling fan is visible above, and a small planter hangs on the wall. The entrance is marked by a glass door, leading into the home.
Guesthouse in Chariton
4.97 out of 5 average rating, 61 reviews

Cozy Country Retreat

Kick back and relax in this calm, stylish space in beautiful Southern Iowa. Home of many white tail deer and trophy bucks. Three miles from Stephen’s Forest public hunting, twenty minutes from the Sprint Car Capital of the Word/Knoxville Raceway, thirty five minutes bites from the Pella Tulip Festival, one hour from the Iowa Speedway, the Iowa Balloon Classic and the Iowa State Fairgrounds.

Top guest favorite
A covered outdoor seating area features four wooden Adirondack chairs positioned around a small table. The space is surrounded by greenery and has decorative elements such as hanging planters. Soft lighting can be seen strung above, creating a cozy atmosphere.
Home in Decatur
4.97 out of 5 average rating, 107 reviews

The Cozy Cottage

We are located 2 miles off I 35 in Decatur City. 10 minutes from Graceland College in Lamoni. 10 minutes from Little River Lake and have parking for boats and outdoor outlet available for charging boat batteries. We love cozy uncluttered spaces to rent and our goal for this Airbnb was to create that for our guests. We offer complimentary bottled water, coffee, tea ,snacks and toiletries.

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