Holiday houses in Osawatomie

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Top-rated holiday rentals in Osawatomie

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

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Top Guest favourite
Home in Fontana
5 out of 5 average rating, 23 reviews

Acres of Life

Take it easy at this unique retreat and tranquil farmhouse getaway. This country escape includes 3 bedrooms, 2 bathrooms, 2 twin sofa beds & loft space. It has a full kitchen, living room, dining room, office & game room. The game room is equipped with a pool table, poker table, pin ball machine, darts, wii & other video games & also includes work out equipment & an infra-red sauna. Tons of movies. Outside, you will find 2 covered decks & a covered patio & covered hot tub. Free farm fresh eggs!

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Guest favourite
A spacious living area showcases a dark sectional sofa paired with a light green armchair. Soft curtains frame the windows, allowing natural light to fill the room. A round coffee table sits on a textured area rug, enhancing the inviting ambiance of the space.
Home in Paola
4.96 out of 5 average rating, 48 reviews

Marie's Place, a cozy house right off the square!

Two bedroom, one bath home with two large living areas, kitchen, laundry room and large front porch. Marie's place is within close walking distance to town square where you can enjoy the fun little shops, antique shopping or even events that take place (craft shows, smoking competitions, car shows, concerts etc.). We are located within walking distance to the Miami County Wine Trolley pick-up spot as well. You can also enjoy golf, fishing, and many other activities within close driving distance.

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Top Guest favourite
Guesthouse in Louisburg
4.96 out of 5 average rating, 155 reviews

Spacious Country Apartment with Modern Amenities

Welcome to Louisburg! Spacious, private entry, 1000 sq. ft. apartment above detached garage within minutes of wineries, antiques & Cider Mill. Set on 15 acres, and 2 miles down a gravel road, you are out of the city and seeing stars, with an amazing 2nd story view. Sleeps up to 6 with separate bedroom with queen bed and low ceiling (62” great for kids!) loft with 2 twins & a double. All wrapped in unique finishes including an amazing shower! Located only 45 minutes from downtown Kansas City!

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Guest favourite
The octagonal cottage is surrounded by a well-manicured lawn and features a stepping stone pathway leading to a patio area. Large windows with shutters offer natural light, and a small air conditioning unit is visible on the side of the structure.
Guesthouse in Eudora
4.89 out of 5 average rating, 257 reviews

Cozy cottage getaway in garden paradise

Get away and relax in a whimsical octagonal cottage surrounded by a lush garden, overlooking a aqua pond and the Wakarusa river. You will have everything you need for a romantic date night or an inspiring place to slow down and reconnect with nature. •1 bedroom open living space with lots of natural light and beautiful views. • Coffee cart with microwave and electric burner and mini frig are provided. • Paddle boat at the lower pond & 2 disc golf nets available for fun. •NO PETS ALLOWED

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Top Guest favourite
An aerial view captures a spacious property surrounded by greenery. A main house, a barn, and additional spaces are visible, with a gravel driveway curving through the lawn. Several vehicles are parked near the entrance, highlighting the expansive outdoor area.
Farm stay in Richmond
4.96 out of 5 average rating, 81 reviews

Rural getaway with incredible views & fishing pond

Relax with the family at this quiet, spacious, 3000 sq ft house on the hill with incredible views of what was called Paradise Valley. Upper level has two bedrooms with king beds, one bath, fully equipped kitchen, dining area, and sunroom/living area. Lower level has two bedrooms, one with queen bed, one with 3 full size beds and bathroom. Separate game room has a pool table, tv, and fridge for entertaining. Property sits on 20 acres with a stocked fishing pond for your enjoyment.

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Top Guest favourite
A welcoming two-story home is surrounded by a manicured lawn, featuring vibrant flower beds. Rocking chairs are positioned on a large front porch with hanging planters. The sun casts gentle shadows across the neatly trimmed grass, enhancing the peaceful outdoor setting.
Home in Cleveland
4.97 out of 5 average rating, 133 reviews

Meadow Brooke Lane

Nested on 3 beautiful acres of fenced land. 4 bedrooms (3 with ensuite), fully equipped kitchen, projector, fire, bbq, plus more! This property is located near multiple event spaces making it ideal for small gatherings or enjoying the countryside. Kids and pets alike with love the vast outdoor space to roam and play. There is a charming train that runs the backside of the property making for a unique and fun backdrop. A fantastic dog friendly brewery is within walking distance.

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Superhost
Home in Rantoul
5 out of 5 average rating, 4 reviews

Rantoul Wilderness Ranch On 440 Acres With Hot Tub

🌾 440 private acres in peaceful Rantoul countryside 🛏 4 bedrooms: 2 queen suites + 2 bunk-style queen rooms (sleeps 14) 🚿 4 ensuite bathrooms + additional full bath ♨️ Hot tub overlooking open Kansas fields 🎱 Game room with pool table, poker table & karaoke 🛶 Private fishing pond with kayaks & life jackets 🔥 Covered patio with fireplace & seating for 20 🍳 Fully equipped kitchen with large island 🥾 Private hiking trails & outdoor games 🚗 On-site parking + keyless entry

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Guest favourite
A cozy living area is showcased with a plush sofa adorned with red cushions, paired with two armchairs. A warm stone fireplace serves as a focal point. Natural light filters through large windows, complemented by vibrant red curtains and decorative pendant lights above.
Apartment in Ottawa
4.89 out of 5 average rating, 278 reviews

The Sherbet Suite

The sherbet suite. This is a mid mod Paradise. Find woods with orange accents adore this beautiful little apartment. Everything is new and comfortable. One block to downtown Ottawa, lots of antique shopping and dinning. Worlds oldest still running movie theater is one block way. Enjoy a beer and bbq in the same block at Not Lost Brewery. In the morning the best little coffee shop in the state is also just one block to the north, Mug Shot Coffee. Look for it in the alley.

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Guest favourite
Home in LaCygne
4.9 out of 5 average rating, 48 reviews

Lake House Getaway, 1 hour from KC!

Enjoy classic lakefront living at this spacious family-friendly lake house in Tanglewood Lakes, LaCygne, KS. Designed to sleep up to 10 guests comfortably, this home is ideal for family vacations, friend getaways, and longer summer stays. With direct lake access, a private dock, and a firepit, it’s the perfect Kansas lake escape for relaxing days and memorable nights. Water conservation is key at our house as it’s on holding tanks. Reach out with any questions.

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Top Guest favourite
A cozy bedroom showcases a black metal bed frame with white linens and decorative pillows. Exposed wooden beams highlight the ceiling. A small dresser and a potted plant are positioned beside the bed, and natural light filters through sheer curtains on the window.
Barn in Iola
4.97 out of 5 average rating, 140 reviews

Prairie Barn Cabin - Iola, KS

Prairie Barn Cabin is a rustic 120+ year old barn featuring exposed beams and modern farmhouse charm. The cabin comfortably sleeps 4 with 2 bedrooms featuring queen sized beds, the bedrooms are accessed by stairs and are connected by an open walk way featuring the exposed beams. The fully stocked kitchen is ready for a meal, and there is a laundry area for use. Watch the native wildlife in the wooded area surrounding the cabin just 3 miles north of Iola, KS.

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Top Guest favourite
An open concept living area showcases wooden ceilings and a blend of modern and rustic decor. A dining table for six is positioned near large windows, while a cozy seating area features a gray sofa and an entertainment unit with a television. A spiral staircase leads to the lofted areas.
Cottage in Paola
4.97 out of 5 average rating, 146 reviews

Cozy Historic Schoolhouse w/ Hot Tub + Views

✨Historic Charm Meets Modern Comfort on the Kansas Prairie✨ Vickers Schoolhouse at Crimson Ridge Flower Farm ★★★★★ “Truly a treasure! So cozy and quaint!” Looking for a peaceful countryside escape that feels a world away—but is still close to everything? Whether you’re planning a romantic getaway or a girls’ weekend full of laughter and relaxation, this beautifully restored 130+ year-old schoolhouse offers the perfect mix of nostalgia, charm, and comfort.

LocationFamilyLong stay

Guest favourite
An open living area features a queen bed covered with a textured blanket, complemented by natural wood accents. A small kitchenette and dining area are visible in the background, along with a loft accessed by a wooden ladder, creating additional sleeping space.
Tiny home in Mound City
4.91 out of 5 average rating, 45 reviews

Studio style tiny home

This cozy tiny home offers, one open living area with queen bed, one bathroom, and a loft with additional full bed (better suited for children, but adults can use). Centrally located in Mound City, but in a quiet setting overlooking 4 additional lots. The vaulted ceilings, natural light, and neutral color scheme, leaves you feeling refreshed. Come enjoy historic Mound City and the surrounding area.

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Popular amenities for Osawatomie holiday rentals