Holiday rentals in Osage

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!

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.

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.

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!”

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!

Cozy Home Near Keystone Lake| 2BR |Family Friendly

Rustic 2BR guesthouse just 5 min from Keystone Lake! Perfect for families, couples, or friends seeking lake fun. Full kitchen, cozy gathering space, and private outdoor yard with pup-friendly amenities. Explore Keystone Lake just moments away! Enjoy fishing, boating, or scenic lake days. Ideal weekend escapes, a quick getaway, or tranquil stays near the water. Enjoy a full kitchen with essentials, includes Wi-Fi, laundry, coffee setup. Only a short 30 minutes from downtown Tulsa!

DillyRanch - A small Homestead Property

Enjoy the sounds of nature when you stay in this unique place. The sounds of nature start at about 5am with the Roosters waking up.....and possibly waking you up. Once the sun comes up the ducks will chime in. The Bunny's usually don't talk much, however the dog may bark and the cat's might start a fight. Located about 20 min outside of Tulsa and about 5 min away from Keystone Lake this one acre property is surrounded by trees and it feels like being far away from civilization.

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!

The Tiny House - Cabin with Ponds on 40 Acres

The Tiny House at R&R Retreat is a rustic getaway situated on 40 private acres with 3 ponds (covering a combined 10+ acres!), lots of trails, wildlife, and tons of natural beauty, all conveniently located 5 minutes from downtown Sapulpa (and historic Route 66!) and 25 minutes from Tulsa. One of five creative cabins custom-built on the site by our family, the Tiny House provides big relaxation in a one-of-a-kind "tiny" package.

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.

The Nest - Luxury Cottage in Charming Locale

Each cottage has an open, spacious floor plan that includes a king-size bed, a fully equipped kitchen, with a Keurig coffee maker, a luxurious bathroom with large walk-in shower and stand alone bathtub, a comfy sofa with pull out bed and a cozy gas fireplace. The cottages are located just off Lover’s Lane. Take a stroll, check out a fishing pole and head over to the pond, or take our canoe out for a spin.

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.