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

*Winter Getaway* 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
The living area features a green sectional sofa with a coordinating ottoman, alongside a wooden dining table set for two. Warm terracotta walls contrast with decorative wall art. Natural light fills the space, illuminating elegant hardwood flooring and inviting a cozy ambiance.
Apartment in Chariton
4.97 out of 5 average rating, 67 reviews

King Bed, Pet Friendly, Main Floor, Walk Downtown

Welcome to our one-bedroom apartment in the quaint town of Chariton. Perfect for couples, solo adventurers, or business travelers, this cozy space seamlessly blends modern comfort with the timeless charm of a historic building. Located just two blocks from the town's charming historic square, you'll have easy access to local shops, restaurants, and more. Whether you're here to explore or unwind, you’ll love the peaceful vibe of our apartment. Pet-friendly—bring your dog along for a fee. 🐶

Top guest favorite
A private patio area is sheltered by a wooden overhang, featuring a comfortable seating arrangement. Decorative lights hang from the ceiling, and a small wind chime adds a subtle decorative touch. Lush greenery surrounds the space, offering a sense of privacy.
Guest suite in Des Moines
4.98 out of 5 average rating, 606 reviews

Cozy, Private Guest Suite & Backyard Oasis

Enjoy a peaceful stay in our private basement suite. You'll love the tall ceilings, natural light, and watching wildlife in our backyard! Private entrance from the back patio, & off-street parking for 1 car. Includes: 1 bedroom with queen bed, bathroom with shower/tub, full kitchen, living room with futon couch, floor mattress, and pack 'n play. Ask for pet policy before booking. If interested in a blocked date, message me (new job=less weekly availability). 10% discount for educators 🏫❤️.

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, 370 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
Condo in Winterset
5 out of 5 average rating, 25 reviews

Luxury 2 Bed/2 Bath Condo-1 Block to Downtown

Experience luxury in this 2-bedroom, 2-bath condo on Airbnb, designed for relaxation and comfortably sleeping four guests. Highlights include an elegant fireplace for cozy evenings and a fully equipped kitchen for gourmet meals. Nestled in a prime location, this condo promises both comfort and convenience, making it an ideal choice for travelers seeking a blend of luxury and practicality. Enjoy unwinding by the fire or exploring nearby attractions for an unforgettable stay.

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 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, 254 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
A cozy green house with white shutters sits among lush grass and large trees. The front yard includes a small seating area with chairs and a decorative fence, offering a welcoming entryway. The paved walkway leads to the front door, enhancing accessibility.
Cottage in Minburn
4.96 out of 5 average rating, 337 reviews

Kim's Kottage on the RRVT, in Minburn, IA.

This home is perfect for the Cycling Enthusiast, a couple, family or small group of friends. This fully furnished cozy 2 bedroom home is sure to please. Located 1 block from the Raccoon River Valley Bike Trail (75 mile paved loop), 15 minutes from I-80 and 30/40 minutes from the State's Capital City of Des Moines, Minburn is the "Small Town with a Big Heart". There are two City Parks, an outdoor historical roller skating rink & 2 Rest/Bars.

Top guest favorite
A compact living space includes a queen size bed, a sleeper sofa, and a small dining table with two chairs. Natural light is provided by a window, and a ceiling fan contributes to airflow. Warm wood tones and neutral colors create a cozy ambiance.
Guest suite in Grand River
5 out of 5 average rating, 16 reviews

Palmers Hideaway

Our smaller unit is like a hotel room. It has a queen size bed and a sleeper sofa. You have your own small kitchen. A patio in the front that over looks the back yard and the burn pit. The small bathroom has a fabulous shower and plenty of hot water. Stocked with fluffy towels and comfy bedding this place is truly a hideaway. The kitchenette has a microwave, nice slice fridge and plenty of other kitchen utensils and dishes.

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