Holiday rentals in Osage County

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!

Modern Log Cabin with Indoor and outdoor hot tubs

We provide FREE HOMEMADE WAFFLE BATTER FOR OUR WAFFLE MACHINE! 1500 Sq Ft Secluded Cabin newly built on 10 acres. 3 Arcade games Heated fire pit & grill on porch. Spacious shower with "his and her" shower heads and bench for shaving or relaxing. 2-person indoor jacuzzi tub and also outdoor hot tub! Right in front of the Tulsa Botanical Gardens. 7 mins. from downtown and just 3 mins from Osage Casino and Resort. Enjoy ziplining 4mins away at Post Oak Lodge and Resort. Mins to Gilcrease Museum

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!

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, 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!

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.

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.

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!

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.

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.

Cottages on The Prairie, the Ranch House.

Centrally located in historic downtown Pawhuska. Cottage has two bedrooms with king sized beds, dresser and walk in closets. Full bath, living room with vaulted ceiling. Full kitchen with dishes, cooking pans and utensils. Also a coffee bar with different coffees and teas. There’s a large dining table with plenty of room for eating or playing games. Exquisite woodwork and decorated with charm. Outside you’ll find a large pavilion with tables and plenty of seating.

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.

Sunny’s Hut at Three Ponds Community

This cute little hut sits just behind our main house. You get your own private space on the land. 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 amazing compost toilet for a truly unique experience. Included in the hut is a mini fridge, microwave, pour over coffee, along with plates, utensils, and towels.