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, 132 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
An aerial view captures the spacious property set against a backdrop of mature trees and open landscape. The newly remodeled home features a large, dark roof, a garage, and a beautifully constructed outdoor space that includes a regulation-size pickleball court with a blue enclosure.
Home in Cleveland
4.99 out of 5 average rating, 110 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!

Superhost
A rustic cabin is nestled among lush greenery and tall trees, featuring a log exterior and a metallic blue roof. A small porch is visible at the front, surrounded by potted plants, while a wheelbarrow rests nearby in the natural setting.
Guesthouse in Skiatook
4.8 out of 5 average rating, 137 reviews

Cabin in the Osage Woods

This is a lovely cabin in the woods - sitting next to my home.( about 150 feet away) The area could be described as "rustic"- insofar as it IS the Oklahoma Osage Hills- 20 miles via a nice drive into Tulsa. Also about 45 minutes from Pawhuska, Oklahoma, home of the Osage Nation - and the Pioneer Woman, Ree Drummond. The view is overlooking the Osage Hills of Oklahoma. You can be as private as you want, or hike, drive to the lake, kayak. Peaceful and serene. Perfect for rural- loving folks.

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
4.97 out of 5 average rating, 115 reviews

The Overlook @ Keystone Lake

Great getaway location! You are entirely to yourself. Overlook is "attached to main house...but not "in" 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 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, 324 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
4.99 out of 5 average rating, 292 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. ✔ 4 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, 222 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.

Superhost
A bright living space features a vibrant pink sofa paired with a colorfully styled coffee table. An open kitchen is visible in the background, equipped with modern appliances and stylish bar stools. Soft lighting enhances the welcoming atmosphere of the area.
Home in Tulsa
4.91 out of 5 average rating, 124 reviews

Colorful Cottage-Downtown

Cute, Colorful, & Charming 1920s 1 bedroom 1 bath cottage. This tiny home has been update to include modern amenities while preserving the original character from nearly 100 years ago. We are located in the Historic Heights Neighborhood just north of downtown Tulsa. Perfect location for events at the Tulsa Arts District, Cains Ballroom, the BOK center, Cox Event Center, and OneOK Field. Just steps from the neighborhood restaurant Prism Cafe and Origins Coffee Shop!

Top guest favorite
A modern living space features a grey sofa with decorative pillows, a coffee table, and a small dining setup with two chairs. Large windows allow natural light to fill the room, showcasing contemporary decor and wood flooring.
Apartment in Downtown Tulsa
4.94 out of 5 average rating, 681 reviews

Location..Location..Location! Cozy Modern Apt

Newly renovated historic building in downtown Tulsa and close to everything! Walk across the street to the BOK Center, a few blocks from Cox Business Center, Cain’s Ballroom, Drillers Stadium, Brady Theatre, the Performing Arts Center..minutes from the Gathering Place, Utica Square Shopping, Cherry Street and River Parks. Only a 10min drive to the airport and the fairgrounds. All furnishings are West Elm. Washer/dryer inside the unit. Gym access

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, 580 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.

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, 260 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.

Superhost
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
4.85 out of 5 average rating, 176 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.

Popular amenities for Osage vacation rentals

  1. Airbnb
  2. United States
  3. Oklahoma
  4. Osage County
  5. Osage