Holiday houses in Osage County

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Top-rated holiday rentals in Osage County

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

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Top Guest favourite
A spacious regulation-size pickleball court is beautifully illuminated with professional lighting. Adjacent to the court, a basketball hoop is visible. The area is surrounded by a secure fence, and a shaded seating area is located nearby for relaxation.
Home in Cleveland
4.99 out of 5 average rating, 126 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 favourite
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
4.97 out of 5 average rating, 71 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 king couch that converts to a bed, a fold out bed/chair and a double air mattress on frame found in the bathroom cabinet. There is also an event center at the same location that is a communal space for guests or booked separately.

Top Guest favourite
Cabin in Pawhuska
4.92 out of 5 average rating, 546 reviews

The Cabin @ The Lodge at Taylor Ranch

The Lodge at Taylor Ranch is home to two of Oklahoma's premiere disc golf courses, but we offer more than just disc golf! Our rustic, yet cozy cabin sits just above the water! In the winter you can snuggle up next to the fireplace or in the summer you can jump off the dock and go swimming! We are 6 miles away from The Mercantile (10 minute drive). We have hosted many Weddings, Parties, Disc Golf Tournaments, Retreats, Boy Scout Camp-outs, Fishing Derbies, etc! We also have an RV Park as well!

Guest favourite
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
4.81 out of 5 average rating, 149 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 favourite
Place to stay in Cleveland
4.97 out of 5 average rating, 140 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 favourite
Home in Pawhuska
4.99 out of 5 average rating, 315 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 Bedrooms ✔ 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 favourite
A spacious outdoor pavilion features ample seating and a large table, illuminated by string lights. Lush greenery surrounds the area, enhancing the atmosphere for gatherings. Comfortable chairs and sofas invite relaxation, while decorative planters add a touch of charm.
Home in Pawhuska
4.99 out of 5 average rating, 436 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 favourite
Tiny home in Ochelata
4.99 out of 5 average rating, 336 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 favourite
A log home exterior is highlighted, featuring an inviting wooden porch leading to a white door. The natural textures of the log walls are visible, complemented by sunlight casting gentle shadows on the floor. The surrounding landscape is seen in the distance.
Cabin in Sperry
4.94 out of 5 average rating, 231 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 favourite
A modern cabin is shown nestled among sparse trees, with soft light glowing from large windows. The cabin features a simple metal roof and a wooden deck that extends from the structure. A winding path leads through the natural surroundings.
Cabin in Pawhuska
4.98 out of 5 average rating, 152 reviews

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

A modern cabin in town! 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. 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. Perfect for a couples weekend, or a quiet getaway. Queen bed in the loft and a queen Murphy bed in the main room. A wilderness retreat within the city limits!

Guest favourite
Farm stay in Pawhuska
4.95 out of 5 average rating, 274 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 favourite
A spacious interior features a cozy bed draped with soft linens, complemented by a bedside table holding books. A small dining table with black chairs is positioned near large windows, offering views of the surrounding landscape and natural light throughout the space.
Dome in Bartlesville
4.93 out of 5 average rating, 99 reviews

Unique Geodome Escape Secluded Stay n Osage County

Welcome to DomeVista, a modern geodome where cozy comfort meets wide-open skies. Stargaze through the skylight, sip coffee on the deck, or relax by the firepit overlooking the pond. With a king bed, cold AC, and a hot shower, this is glamping elevated. Just minutes from Bartlesville, Woolaroc, Bluestem Falls, and The Pioneer Woman Mercantile, DomeVista is the perfect blend of nature, comfort, and convenience.

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