Holiday houses in Osawatomie

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Top-rated holiday rentals in Osawatomie

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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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Guest favourite
Home in Fontana
5.0 out of 5 average rating, 24 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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Top Guest favourite
An open-plan dining and living area features a long dining table with black chairs. Off to the side, a cozy seating arrangement includes a sectional sofa and a coffee table. Natural light floods through large windows, and warm wood paneling creates a comfortable ambiance.
Loft in Louisburg
4.97 out of 5 average rating, 75 reviews

Modern Loft w/ Brick Walls, Pool Table + Sleeps 12

You are going to LOVE the Lowman Loft - a beautifully refurbished historic building right in the center of Louisburg, Kansas. Only straight highway 40 miles from Kansas City. The loft is 3,000 sq ft. Open dining, living and kitchen areas and four private bedrooms. A perfect option for your friends, families, or workmates, the loft is located in a beautiful neighborhood surrounded by antique shops, local wineries, and wedding venues that you can explore. A short drive to Overland Park or Olathe.

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Top Guest favourite
Home in Ottawa
5.0 out of 5 average rating, 30 reviews

University Cottage

Bring the whole family, including pets, to this thoughtfully remodeled home. Located across from Ottawa University, this 4 bedroom 2 bath house comes with a delightful sun-room, an extra living space, and a large fenced back yard. Home is located approximately 1.5 miles from the Franklin County Fairgrounds (Celebration Hall), a half mile from the Prairie Spirit Rail Trail, and mile from downtown Ottawa and Ottawa Municipal Auditorium. KU-30 min MCI-75 min KC/Kauffman/Arrowhead Stadium-1hr

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Top Guest favourite
Guesthouse in Louisburg
4.96 out of 5 average rating, 158 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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Top Guest favourite
The image features a modern cabin with wooden exterior, surrounded by lush greenery. A solar-heated swimming pool reflects the serene sky, with inviting lounge chairs positioned on a wooden deck nearby. Natural light highlights the architecture, enhancing the connection with the outdoor environment.
Cabin in Pleasanton
4.93 out of 5 average rating, 29 reviews

Luxe lake cabin 1hr to Kansas City w pool+hot tub

Welcome to the Butterfly Pods, by PodHopping, where eco-conscious living meets modern comfort in our Passivhaus-standard cabins. We generate our own power, manage our own water, and work with nature’s rhythms. It’s a chance to slow down and reconnect with the earth, and your loved ones. Lounge in a hammock, swim, soak in the hot tub, kayak on the lake, and gather around the fire. Come experience off-grid living and leave refreshed, with a greater appreciation for the resources we all share.

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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, 82 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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Guest favourite
A modern living area features a blue velvet sectional sofa adorned with bright yellow pillows. A golden armchair complements the space. Natural light filters through the blinds, highlighting a decorative area rug. A small Christmas tree stands nearby, adding a festive touch.
Apartment in Ottawa
4.91 out of 5 average rating, 176 reviews

Peacock Place

Peacock Place. This is a mid mod Paradise. Find woods with gold, yellow and blue accents adorn 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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Top Guest favourite
Two sets of glass doors open to the indoor swim spa, framed by textured turquoise walls. A cozy seating area with a hanging chair and a small table is positioned nearby, along with greenery that adds a touch of nature to the space. Robes hang accessible on hooks.
Home in Eudora
4.97 out of 5 average rating, 117 reviews

The Cottage: Luxurious Getaway!

Escape to luxury at this private cottage with indoor 17-ft swim/spa, sauna, and steam shower. Sleeps up to 10 with beds, air mattresses, and convertible furniture. Enjoy a fenced patio, fire pit, robes, slippers, face masks, Nespresso, and more. Perfect for a romantic getaway, group stay, or small event (max 15). Includes kitchen, lounge areas, smart tech, and walkable access to downtown Eudora. No pets. Quiet hours 10p–8a. Swim at your own risk. Property is not child-proof.

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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, 142 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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Guest favourite
Home in La Cygne
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
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.

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