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Holiday houses in Osceola

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Top-rated holiday rentals in Osceola

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

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Top Guest favourite
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, 196 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 favourite
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
4.99 out of 5 average rating, 139 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 favourite
A cozy living area features a plush sofa alongside two armchairs positioned around a low table. Soft lighting from a nearby lamp creates a relaxed ambiance. Decorative elements, including a bookshelf and a neatly arranged rug, enhance the inviting atmosphere.
Cabin in Pella
4.96 out of 5 average rating, 173 reviews

The Prayer Cabin

The Prayer Cabin is located at Lake Red Rock outside of Pella, IA. The cabin Is an Earthen/Berm home located on a 1 acre lot in a quiet & clean neighborhood. The lot boasts a wooded valley with many birds and squirrels to watch. The Prayer Cabin was recently remodeled with a brand new kitchen and bathroom. Our first guests asked us if Chip and Joanna were the creators of the design. 💚 Navy Blue cabinets, Tons of white shiplap and open shelving. Peaceful. A place of respite and relaxation.

Top Guest favourite
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, 374 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 favourite
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, 48 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 favourite
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, 149 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 favourite
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, 224 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 favourite
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, 115 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 favourite
A light-filled kitchen features open shelving adorned with colorful glassware and decorative items. A modern refrigerator and pink microwave complement the white cabinetry. A central island with bar stools offers seating, while a floral arrangement adds a touch of charm.
Apartment in Stuart
4.99 out of 5 average rating, 158 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!

Guest favourite
A group of bison stands in a grassy field, with several individuals facing the camera. The landscape is open, showcasing a natural pasture environment under a cloudy sky. The bison exhibit their characteristic large build and thick fur.
Farm stay in New Virginia
4.9 out of 5 average rating, 63 reviews

Bison Ranch Cabin

Stay on a BISON FARM! At the Tatanka Ranch you will experience the beauty of the countryside with breathtaking views of the majestic bison. Enjoy a fully equipt kitchen to cook and dine-in. There is Wifi available. The patio looks out onto the timber and bison farm. There are no steps to enter the AirBnB and the doorways are wide. Easy access. Flex space for office.

Top Guest favourite
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, 314 reviews

Debbie's Komfy Diggs Winter Set

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.

Guest favourite
A dining area features a sleek, high-top table surrounded by four matching stools. Natural light filters through two large windows, framed by dark curtains. A contemporary light fixture hangs above, complementing the space's neutral color palette and enhancing the overall atmosphere.
Home in Osceola
4.88 out of 5 average rating, 33 reviews

Downtown Cottage.

Keep it simple at this peaceful and centrally-located place. It’s an older home that has been remodeled to sleep 4-5 people. It has 3 beds; Queen,Full,and Twin;as well as a hideaway in a couch. Has all your basic amenities. It’s within walking distance of the downtown square that has some unique restaurants as well as Fareway Grocery.

Popular amenities for Osceola holiday rentals

  1. Airbnb
  2. United States
  3. Osceola