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Vacation rentals in Osceola

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Osceola

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

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Top guest favorite
The front exterior of the house features a broad staircase leading to a glass-paneled door framed by two large pillars. Multiple windows are visible, allowing natural light to enter, while a well-kept yard surrounds the entrance, contributing to the inviting facade.
Home in Guthrie Center
4.94 out of 5 average rating, 168 reviews

Small Town Mansion

Step into the charm of this beautiful early-1900s Sears & Roebuck home—truly a one-of-a-kind getaway. Located in the heart of Guthrie Center, you’ll be just 15 miles north of I-80 and 8 miles west of Lake Panorama. Enjoy peaceful mornings on the front porch or stretch out and relax in the spacious living room. A large and thoughtfully curated book collection awaits any reading enthusiast. The entire home is yours to settle into, unwind and make your own! Ample parking-double car garage & street.

Guest favorite
A serene lakeside setting is captured at twilight, featuring a glowing campfire surrounded by stones. A wooden picnic table is visible nearby, and a dock extends into the calm water, reflecting soft light from lanterns along the shore.
Tiny home in Norwalk
4.98 out of 5 average rating, 150 reviews

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.

Top guest favorite
Apartment in Winterset
4.94 out of 5 average rating, 393 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
The mid-century modern cottage is set on a lush green landscape, featuring a unique stone and metal exterior. Generous windows provide views of the surrounding nature, while a covered porch offers seating options for relaxation. A large tree stands nearby, enhancing the peaceful setting.
Farm stay in Indianola
5 out of 5 average rating, 101 reviews

Cottage getaway; perfect for some relaxation

Come stay in this lovely mid-century modern cottage located between Norwalk and Indianola and just 30 minutes south of Des Moines, 15 minutes south of the DSM airport. Enjoy a full kitchen with an open layout and large living space, private bedroom with a queen-sized bed, large walk-in closet, and full bath. Coffee, tea, and breakfast pastries included. Beautiful views in every direction; come enjoy some downtime in this relaxing getaway. Check out our IG page! @olio_farm

Top guest favorite
A vintage red Farmall tractor is positioned on a concrete slab, with large black tires prominently displayed. A white barn in the background features a painted American flag. The surrounding area includes grass and distant cylindrical bales of hay under a clear sky.
Barn in Chariton
4.95 out of 5 average rating, 41 reviews

Barndominium with Goats!

Escape to our cozy barndominium nestled among the rolling hills of Southern Iowa, where tranquility meets adventure! Perfect for hunters and fishermen, couples, or solo travelers, this unique getaway offers a slice of rural paradise surrounded by acres of timber and cropland. Perfect for Hunters and Fishermen! Public hunting and fishing nearby. Just down the road from Red Haw State Park and Rathbun Lake and Honey Creek Resort. Inquiry about rights. Goats and chickens nearby :)

Top guest favorite
Home in Afton
4.99 out of 5 average rating, 152 reviews

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.

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, 259 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
The exterior of a galaxy bell tent is softly illuminated by string lights, highlighting its unique shape. The surrounding area features a natural landscape, with trees visible in the background, creating a serene nighttime setting.
Tent in Perry
4.95 out of 5 average rating, 235 reviews

Relaxing galaxy bell tent getaway

Come sleep under the stars in this cozy galaxy bell tent. You can enjoy a good nights sleep in the comfortable King bed and stay comfortable with an air conditioner and heater. There is also a fridge for keeping your food fresh. Soak up nature while you hike the trails around Oak Haven Acres, a 32 acre farm in rural Iowa. For your security we have a trail camera at the beginning of the driveway that won’t intrude on your privacy.

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
4.98 out of 5 average rating, 124 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.

Top guest favorite
Apartment in Stuart
4.97 out of 5 average rating, 171 reviews

The 1894 by Doe A Deer | 2 br, 1 bath apartment

Welcome to The 1894 by Doe A Deer - a newly renovated 2 bedroom spacious apartment located in historic downtown Stuart! Enjoy restaurants, boutiques and coffee just steps from the front door. Relax and enjoy the view from your new favorite small town spot. Perfect for getting ready with your wedding party, families, girls trips, anniversaries & more! We can’t wait to host you!

Top guest favorite
Cabin in Osceola
4.93 out of 5 average rating, 15 reviews

Relaxing pond house nestled in nature

A comfy cozy pond house is waiting for you to kick back and relax . Water,nature , and farm fields surround this peaceful oasis . Catch up on movies, read a book,sip your coffee and watch the geese land on the water , cast your fishing line and watch the bass do a dance, paddle around the pond in the paddle boat, take a walk , you won’t be bored!

Top guest favorite
A front view of the home features a well-maintained entrance with two chairs positioned beside a small porch. A concrete driveway leads to a garage door, while the surrounding landscaping includes a grassy area and decorative elements near the entrance.
Home in Winterset
4.97 out of 5 average rating, 327 reviews

Debbie’s Komfy Diggs Winterset

Whole home, two bedroom, full kitchen, pet friendly and close to beautiful downtown historic Winterset. Home of John Wayne and the Bridges of Madison County. My name is Debbie, I have lived in Winterset for over fifty years. Can keep you informed of coming events and maps of the area. Located 13 miles from Interstate 35 and Interstate 80.

Popular amenities for Osceola vacation rentals

  1. Airbnb
  2. United States
  3. Osceola