
Vacation rentals in Osceola
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Top-rated vacation rentals in Osceola
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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.

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.

Effortless Landing near Airport
Welcome to the Effortless Landing! Our super clean and comfy, Boho style retreat. Private keyless entry with off street parking. Enjoy a queen bed, additional pull out queen bed in the couch, great local coffee, & all the amenities like fiber wifi, TV, full kitchen, & laundry. Add that to the wonderful surroundings of the city of Des Moines, in a quiet, centrally located neighborhood. Conveniently located 4 minutes from the Des Moines International Airport, & 7 minutes to Downtown Des Moines!

Charming 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.

The Legacy Stone House
The most unique stay in Winterset! Legacy Stone House AirBnB is a historic residence located one mile east of Winterset, Iowa. Built in 1856 during the Settlement Era of Madison County, it is one of nearly 100 stone houses built during that time in the area. Officially named the William Anzi Nichols House, it is listed on the National Register of Historic Places. Convenient centralized location if visiting Madison County’s six covered bridges and two minutes from grocery, gas and dining.

The Carol Anne-Charming 2bd/2ba Victorian near DT!
This Victorian-era duplex is the perfect mix of Victorian and modern for all the comforts of home. Perfect for quick or extended trips. Location can't be beat: Walking distance to Drake University. Minutes by car to downtown, hospitals, Ingersoll district and proximity to I-235 gets you anywhere in the city. Off street parking/electronic locks make check-in a easy. 2 large bedrooms w/queen beds, 2 bathrooms, kitchen, laundry, closets, and more making it ideal for multiple guests!

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.

Country peace
cabin was built for us to live in while our house was being planned and built. cabin is on 5.9 acres. out door tent area with fire pit. BBQ grill and park style grill with picnic table and yard swing. lots of room for walking and watching deer. Central Air and space for parking . cabin has a storm shelter. We are within 5 miles of one of the covered bridges of Madison county. Other covered bridges are close. Other sites, under ground railway house. John Wayne childhood home.

The Country Oasis
Welcome to your perfect retreat—where comfort, style, and thoughtful details come together. The Country Oasis offers beautifully designed spaces to relax, recharge, and connect. This inviting 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.

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.

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.

Etta’s Place - private 1b/1b - MidCentury Modern
We love our neighborhood and are excited to share it with you! We have partnered with local restaurants, bars, coffee shops, boutiques, & tea shops to offer exclusive discounts to guests of “Etta’s Place.” It’s our hope that this Airbnb allows you to enjoy the wonderful Ingersoll District. Des Moines is a great place to visit, lots of outdoor activities, amazing food, and unique experiences around every corner!
Popular amenities for Osceola vacation rentals
Other great vacation rentals in Osceola

Retro Studio in Historic Building

Cheerful & Cozy Studio - Fully Private Entrance

The Draper-MCM Spacious Ranch minutes to it all

Relaxing pond house nestled in nature

Secret Garden Suite

Squareview Stays - Modern Apartment on The Square

Auspicious Penthouse Studio Elevated King

Bison Ranch Cabin
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