Vacation rentals in Osage County

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Top-rated vacation rentals in Osage County

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Guest favorite

A scenic aerial view showcases lush green fields and dense wooded areas surrounding a winding river. The landscape displays varied textures and tones, with a light blue sky above, hinting at the peaceful rural setting close to the modern cabin.

Cabin in Pawhuska

4.98 out of 5 average rating, 118 reviews

Bridgewater Cabin (Modern/private/in city limits!)

A modern cabin in town! Whether you are looking to relax on the 320sf deck by the house, or walk just a few steps down a wooded path to the platform overlooking Bird Creek. Lots of wildlife can be seen. This is the only residence on 4.2 wooded acres, and feels like you’re miles from town. Located 3 minutes drive from downtown Pawhuska. Perfect for a couples weekend, yoga or artist getaway. Queen bed in the loft and a queen Murphy bed in the main room. A wilderness retreat within the city limits!

Top guest favorite

Home in Cleveland

4.99 out of 5 average rating, 102 reviews

Skyline Paradise | Pickleball & Bball |Keystone Lk

Luxury Retreat with Tournament-Grade Pickleball Court Experience this stunning hilltop oasis near Keystone Lake, featuring a brand-new (2025) regulation-size pickleball court with pro lighting, a basketball area, & endless entertainment—cornhole, jumbo Jenga, arcade games, air hockey, foosball & more! • 3,200 sq. ft. on 3.5 acres • Stocked kitchen • 30 min to downtown Tulsa • Three-level deck with breathtaking views • Dog-friendly (3 under 80 lbs, $125 fee) Book now for the ultimate retreat!

Top guest favorite

A serene lake scene captures a vibrant sunset reflecting on the water, with silhouettes of trees along the shore. Gentle ripples create a shimmering effect, while varied cloud formations enhance the expansive sky filled with warm hues of orange, pink, and blue.

Place to stay in Cleveland

4.96 out of 5 average rating, 104 reviews

The Overlook @ Keystone Lake

Great getaway location! You will feel entirely to yourself. Room is "attached to house...but not "in" the main house. Private entrance, no shared spaces. Very private & tranquil space! Relax in a country setting with "to die for" panoramic views from 90 feet above the water. Wildlife galore, including Bald Eagles. A perfect couples escape, girl’s weekend or some individual solitude ! Covered/enclosed hot tub room with great views. Adults Only! (18+) Check out our “extra amenities.”

Top guest favorite

The front view of the cabin showcases its rustic charm, framed by vibrant yellow leaves in autumn. The cabin features large windows, inviting natural light inside. A second-floor balcony overlooks the scenic wooded surroundings, creating a harmonious blend with nature.

Guesthouse in Bartlesville

4.92 out of 5 average rating, 195 reviews

Cabin in the Woods, 10 minutes to Bartlesville

Our guest cabin is set on 20 wooded acres in the Osage Hills at the end of a private gravel road. It feels completely isolated, but it's only 10 minutes to downtown Bartlesville, 20 minutes to Pioneer Woman's Merc, and an hour to Tulsa. There is a full kitchen, living area, and full bath on the ground floor, with a queen and twin bed on the 2nd floor. There is no TV to interfere with the quiet, although WiFi keeps you connected. We live in the main house and are always available if needed.

Top guest favorite

A newly constructed white cottage showcases a bold red door and is framed by a white picket fence. The front yard features neatly trimmed grass and vibrant flower beds. Nearby trees provide shade, enhancing the welcoming exterior.

Home in Pawhuska

4.99 out of 5 average rating, 386 reviews

Cottages on The Prairie, the Farmhouse

The Farmhouse is one of 4 cottages that are newly constructed in Pawhuska. Living room with vaulted ceiling, full kitchen with dishes, pots and pans and utensils. Coffee bar with various coffees and teas, sweeteners and creamers. There is a large dining table with plenty of room for eating or playing games. Special touches with exquisite woodwork and decorated with charm. Outside is a large pavilion with tables and plenty of seating. These cottages are one street over from the Mercantile.

Top guest favorite

A tranquil view of a cottage situated beside a small private lake, surrounded by lush greenery. The calm water reflects the natural scenery, while trees line the shore. The cottage features a wraparound porch, providing a serene and picturesque setting.

Tiny home in Ochelata

4.99 out of 5 average rating, 319 reviews

Private cottage on small lake.

Only 35-40 minutes away from Pawhuska & 15 from Woolaroc, this cottage sits on a small private lake in a gated 65 acre private estate. There are more friendly animals than people at this estate; 29 goats, 8 mini donkeys, 4 horses and more! With a queen sized bed & a small bunk room w/ twin bunks it will comfortably sleep 2 adults & 2 small people. The cottage has a small kitchen w/ a refrigerator, 2 burner stove, microwave, toaster oven, toaster, dishes, etc. A firepit and grill outside.

Top guest favorite

A charming farmhouse is framed by a picket fence, set against a backdrop of lush greenery. The exterior features a mix of large windows and cozy porches, illuminating the inviting structure amid a serene landscape.

Home in Pawhuska

5 out of 5 average rating, 273 reviews

StrikeAxe Estate Cottage | Pawhuska’s Historic Gem

Welcome to StrikeAxe! This fully restored 1920s French farmhouse rests on several acres of scenic land, promising a unique getaway immersed in Pawhuska’s beautiful historic charm just a mile from downtown. It provides a lavish base for an unforgettable visit to The Pioneer Woman’s Mercantile with your girlfriends. ✔ 5 Comfortable Brs ✔ Stylish Living Area ✔ Chef’s Grade Kitchen ✔ Private Outdoors (Dining, Gazebo, Fire Pit) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more below!

Top guest favorite

A rustic cabin features a stone façade and a weathered metal roof. A covered porch with wooden support beams provides an inviting entryway. Green shrubs and a stone pathway lead to the entrance, surrounded by trees reflecting the colors of sunset.

Ranch in Osage County

4.96 out of 5 average rating, 125 reviews

The Cabins on Birch Creek - Guest House

Quite and Cozy. Just 10 miles to the Pioneer Woman Merchantile and 18 miles to the Tall Grass Prairie Preserve The Cabins on Birch Creek offer water front access to Birch Creek and a tributary. Spring garden with wild and domestic flowers, a swinging bridge to stroll across and lots of opportunity to see wildlife and domestic animals. This property has a kitchenette, stylish and spacious bathroom, and magnificent outlook from the bedroom. Enjoy coffee on the porch as the sun rises.

Top guest favorite

A comfortable living area features a tan leather sofa with orange accent pillows and a matching chaise lounge. A wooden dining table with four chairs is visible. Light wood paneling and flooring contribute to a cozy, natural ambiance. A ceiling fan above offers airflow.

Cabin in Sperry

4.94 out of 5 average rating, 213 reviews

Gunker Ranch / Log Home

Beautiful, genuine true Log Home in the Osage Oklahoma Hills. Quiet, peaceful area with gorgeous sunrises and sunsets! Surrounded by horses, cattle, goats, and many other type farm animals. Excellent roads to cycle on and take leisurely, relaxing drives. Friendly people who enjoy life in the country - just like you will when you arrive! It is a destination of peace and relaxation. Only 15 minutes north of Downtown Tulsa. Easy drive to any part of Tulsa or Osage County.

Top guest favorite

A renovated Craftsman home is showcased from the front, featuring a symmetrical facade with a dark blue exterior and white trim. Lush greenery surrounds the property, with flower beds adding touches of color. A wide staircase leads to the inviting porch, providing a sense of welcome.

Home in Pawhuska

4.98 out of 5 average rating, 174 reviews

The Oilman’s Daughter On 7th Street

FEATURED IN THE PIONEER WOMAN MAGAZINE Our SECOND LOCATION in Pawhuska is on 12th Street. Resting on a corner lot, blocks from The Pioneer Woman Mercantile, a wonderfully renovated 1925 Craftsman home. You will find luxury throughout, with four bedrooms, three and a half baths. Relax in a rocking chair on the front porch, or in the privacy of the backyard with a fire pit and gas grill. Enjoy the charm of the 1900s & luxury of today.

Top guest favorite

A historic cabin, constructed from native sandstone, is surrounded by lush, green grass and trees. The structure features large windows that reflect the evening light, with a gentle glow emanating from within. A white fence lines the property, enhancing the rural setting.

Farm stay in Pawhuska

4.96 out of 5 average rating, 252 reviews

The Cabin on The Coy T Ranch

Built in 1900, the cabin made of native sandstone sits atop one of the rolling Osage hills. It's fully renovated with hardwood floors, granite counter tops, soaker tub, & views out every window! The cabin faces west and the most beautiful sunsets are the evening's entertainment. Guests will enjoy the privacy of being surrounded by ranch land as far as they can see, yet still partake of the town life just 5 miles away.

Top guest favorite

The exterior of a newly remodeled guest house is shown, featuring a rustic red wooden facade with white trim. A welcoming white door is positioned at the front, and a small wooden deck is visible. The surrounding landscape includes open fields and a bright sky.

Guesthouse in Pawhuska

4.95 out of 5 average rating, 246 reviews

Lemmons Lemman - A Charming Country Getaway

Our recently remodeled guest house is nestled in the heart of Osage County countryside, all while being located less than 10 minutes from downtown Pawhuska. Artfully decorated, it features locally handmade furniture along with beautiful woodwork. Guests can enjoy a relaxing evening by the fire pit, receive a peaceful night's rest, and wake up, enjoying a cup of coffee while overlooking the landscape.