Vacation rentals in Osawatomie

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Top-rated vacation rentals in Osawatomie

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

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Guest favorite
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.

Guest favorite
The cabin exterior features a wooden facade, with a welcoming porch equipped with two chairs and a table. A grill is positioned to the side, and a pathway of stones leads to the entrance. Natural greenery surrounds the area, providing a serene atmosphere.
Cabin in Pleasanton
4.94 out of 5 average rating, 147 reviews

D&B Cabin Rentals Cabin #2

Doug and Becky We offer cabins off of 69 highway in Pleasanton, KS, near 2 lakes! We offer nightly, weekly, and monthly rentals. Each cabin is approx 250 Sq ft. Includes TV, Satellite TV, Gigabit Internet, full bath, kitchenette, grill including propane and utensils, (upon request), and a Porch with chairs and table. Community fire pit and picnic tables available. We have both a coffee maker that uses a filter and grounds, and a Keurig for your K-cups. Bring your favorite coffee! Pet Friendly!

Top guest favorite
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!

Top guest favorite
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.

Guest favorite
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
4.92 out of 5 average rating, 175 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.

Top guest favorite
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, 109 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.

Top guest favorite
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, 129 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.

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

Top guest favorite
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, 138 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.

Top guest favorite
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.

Guest favorite
Cabin in LaCygne
4.95 out of 5 average rating, 21 reviews

Inviting Lakefront A-Frame Cabin

Kansas City FIFA World Cup 2026 dates are now open! Enjoy your relaxing stay in this 3 bedroom 2 bathroom cabin. Wake up to the beautiful sunrise, spend all day kayaking, fishing, and playing games. Then grill out and watch the sun set with the whole family. This is the perfect retreat to get away from your daily stress and get back into nature.

Top guest favorite
The exterior of a charming yellow cottage is displayed, featuring a covered front porch and steps leading to the entrance. Lush green grass surrounds the house, and a cluster of white flowers is visible in the foreground, contributing to a serene rural atmosphere.
Cottage in Lawrence
4.95 out of 5 average rating, 142 reviews

Charming country cottage

Quiet country cottage located a short 5 miles (12 minutes) south of Lawrence. Nestled against a hill with a backdrop of trees, this cute 100 year old house has charm as well as privacy. Located on an 80 acre rewilded farm, The Prairie Harbor, guests will enjoy natural surroundings.

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