Vacation rentals in Osage

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Top-rated vacation rentals in Osage

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Top 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, 117 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

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

A wooden sign displaying 'Prairie's End' is mounted on two sturdy posts, surrounded by lush greenery. The natural wood finish complements the outdoor setting, inviting guests to enter the 40-acre property.

Home in Osage

4.98 out of 5 average rating, 41 reviews

Prairie's End

Discover your personal haven at "Prairie's End", a 40-acre property offering unparalleled serenity. Imagine waking up surrounded by nature and enjoying peaceful walks through the trails, watch the deer and multitude of wildlife. The open space provides a queen bed, a couch that converts to a bed, a double air mattress on frame found in the bathroom closet and a single roll-away bed. There is also an event center at the same location that is a communal space for guests or booked separately.

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, 271 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 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, 211 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 living area features an eclectic seating arrangement with a patterned armchair and a blue sofa. A coffee table holds a decorative arrangement of flowers. Natural light enters through dual doors, flanked by fabric blinds, creating a relaxed atmosphere.

Home in Bristow

4.99 out of 5 average rating, 107 reviews

Quiet Rt. 66 Guest House

Disconnect and take it easy at this unique, cozy getaway. Just one mile from the original 1920s Route 66, our remote private guest home offers the chance for travelers and city dwellers to recharge. Whether you're looking for a stopover on a Mother Road adventure or to get out of town and see the stars, this is the place for you. A full kitchen, washer/dryer and oversized shower add even more comfort. Perfect for your traveling pups with a fenced yard and dog door.

Guest favorite

A large outdoor patio features a wooden deck surrounded by brick walls. Multiple seating arrangements consist of black chairs and tables, along with a central fire pit, creating a spacious area for gatherings and relaxation.

Place to stay in Stillwater

4.83 out of 5 average rating, 548 reviews

Cozy 2BR Private Farmhouse/Full bath/kit/Patio

Welcome to our Cozy Farmhouse on Main St. centrally located less than a mile from Boone Pickens Stadium. Enjoy Free Parking on Game Day and the Cozy Warmth of a 2 bedroom Farmhouse feel with a Large Outdoor Patio. Enjoy Tailgating with family and friends on game day with on our Large Patio, Grill, and Fire Pit. Also included on our Patio, is a Large 40,000 BTU Propane Gas Fire Pit to keep you warm on the cool Fall Football Games.

Guest favorite

The exterior of the Carriage Loft studio is depicted, featuring a private entrance with a modern door and a window nearby. Soft outdoor lighting enhances the entrance, while greenery frames the space, giving a welcoming appearance.

Guesthouse in Tulsa

4.86 out of 5 average rating, 670 reviews

CARRIAGE LOFT -Historic Guesthouse Duplex Downtown

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.

Guest favorite

A geodesic dome is situated on a wooden deck among trees, showcasing its unique triangular windows. A wooden ladder leads up to the entry, and a small outdoor seating area is visible on the deck. Natural surroundings include leaves and shrubs.

Dome in Sand Springs

4.87 out of 5 average rating, 155 reviews

Geodesic Sunset Dome

This cozy geodesic dome has its own private nook overlooking our second pond. Heating and air are a must in Oklahoma and we got you covered so you are comfortable all year long. You also get access to our beautiful outdoor shower and our unique compost toilet for a truly memorable experience. Included in the dome is a mini fridge, microwave, Kuerig coffee, along with bowls, utensils, and towels.

Top guest favorite

A modern farmhouse is set against a backdrop of lush greenery, featuring a covered porch and large windows. A gravel driveway leads to the entrance, framed by trees that provide shade, with an open field visible in the distance.

Home in Tulsa

4.99 out of 5 average rating, 186 reviews

The Scissortail Farmhouse - LAND, HOT TUB, horses!

Looking for a serene escape in a convenient location? The Scissortail Farmhouse is a new guest home nestled on the edge of a working regenerative farm that supplies produce to many of our best local restaurants. It is minutes from the airport, downtown, and popular Tulsa attractions. We hope you enjoy our little slice of country that is about as close as you can get to the big city!