Holiday houses in Osage County

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Top-rated holiday rentals in Osage County

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Top Guest favourite
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, 134 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 rustic cabin nestled among trees and colorful foliage, situated near a calm body of water. An outdoor seating area features wooden chairs, while natural stone borders the landscape. The atmosphere suggests a peaceful retreat away from urban life.
Cabin in Pawhuska
4.92 out of 5 average rating, 557 reviews

The Cabin @ 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!

Top Guest favourite
The exterior of a large farmhouse is shown at dusk, featuring a wraparound porch with porch lights illuminating the space. The white siding contrasts with dark window frames, while landscaped bushes enhance the front yard. A wide driveway leads to the building.
Home in Pawhuska
4.99 out of 5 average rating, 400 reviews

The Farmhouse Relatively Near the Prairie

The perfect place for group retreats, family reunions, and especially girl's weekends. This large farmhouse boasts all the modern conveniences and special touches but retains it's 1920's historic charm. It has all the room needed for you to enjoy a great time together in the common areas: Living, dining, full kitchen, wrap around porch and covered outdoor living space with silo fireplace. Up to 10 Guests can then retreat to 5 bedrooms each with en-suite bathrooms and separate heat and air.

Top Guest favourite
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, 332 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!

Guest favourite
A charming farmhouse exterior is showcased, featuring a large wrap-around porch. Flower baskets hang from the porch posts, complemented by a flagpole displaying the American flag. A spacious lawn surrounds the house, offering a welcoming outdoor space.
Home in Pawhuska
4.82 out of 5 average rating, 267 reviews

The Flamingo's Nest near Pioneer Woman Mercantile

This beautiful 2,800 sq ft farmhouse is great for large groups, or is great for a romantic get a way for two. It's located only a few short blocks from The Pioneer Woman's Mercantile in a great neighborhood. Play a game of pool, a game of foosball, soak in the master tub, or relax around the fire pit on the wrap around porch. Your vehicles will stay safe under covered parking. This home is where Ree’s film crew stays while filming the Pioneer Woman. You won't be disappointed in this rental.

Superhost
The exterior of a charming mid-century farmhouse is displayed, featuring light blue siding and decorative gables. An American flag is situated on the front porch, which is accessed by a curved staircase. Large windows create an inviting atmosphere while greenery frames the structure.
Home in Pawhuska
4.81 out of 5 average rating, 353 reviews

*Farmhouse Cottage* Pet Friendly Near The Merc*

Escape to Osage county where the sky goes on forever and the locals treat you like family. This mid-century Farmhouse has been newly updated with a light and airy farmhouse vibe and finished off with all of the modern luxuries. Rest from a long day of exploring the Osage prairie and sip some wine in the tranquil living area or play some board games on the oversized bunkhouse table. With all of the amenities of home, you are sure to want to return to our little piece of the heartland.

Superhost
A charming cottage features a wraparound porch supported by white columns. Comfortable seating arrangements are visible, surrounded by lush greenery and flower beds. The well-maintained lawn adds to the inviting exterior of the home.
Home in Pawhuska
4.93 out of 5 average rating, 345 reviews

ROSE COTTAGE 🌹🏡

Enjoy a getaway to the quaint and cozy ‘Rose Cottage’ where scenes from “Killers of the Flower Moon” 🎥 have recently been filmed!! 100 year old charming home w/incredible wraparound porch, walking distance to Pioneer Woman’s Mercantile! Ample indoor/outdoor spaces, this beautiful retreat is the perfect place in Pawhuska! Time seems to stand still here, almost like a grandmother’s home. This isn’t a modernized house. Our cute town boasts museums, eateries, shopping, Tallgrass prairie, etc!

Top Guest favourite
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, 454 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.

Superhost
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, 164 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
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
4.95 out of 5 average rating, 283 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
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, 278 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.

Top Guest favourite
Dome in Sand Springs
4.88 out of 5 average rating, 243 reviews

Geodesic Sunset Dome at Three Ponds Community

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 County holiday rentals