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!

The Archer - Cozy Home

Kick back and relax in this calm, stylish, non-smoking space. Easy access to I-244; close to downtown, fairgrounds, Cherry Street, Brookside, The Gathering, Brady District and Tulsa University. Great for weekend or short stay work engagements, campus visits, concerts, sporting events or the fairgrounds. Off street, private parking provided. No smoking, pets, gatherings/parties. Property complies with local licensing requirements. City of Tulsa Short Term Rental License Number: STR21-00223

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.

An Artist's Cozy Log Cabin Minutes From Downtown.

Spend the night in a very Private, Cozy, Eclectic and Historically Imfamous Log Cabin, surrounded by an artist couple's one acre garden. Right by Downtown Tulsa! Located in Historic Owen Park Neighborhood. One of the oldest neighborhoods in Tulsa. Very close to The B.O.K. Arena, Tulsa Ball Park, Cain's Ballroom, Tulsa's Arts District, many restaurants, and the Tulsa Gathering Place. This Cozy cabin is perfect for a couple wanting a relaxing weekend and also a wonderful writer's retreat!

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!”

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!

French Woods Quarters

Our guesthouse has a very warm, peaceful decor to parallel the nature around it. You will likely see many deer and other wildlife from the huge covered back porch while enjoying a meal cooked in your full kitchen. You will also have access to an attached single-car garage where there is also a washer and dryer available for your use. The pool is left open year round. Whether you need a place to get away and relax or place to call home while you're traveling for work, this is your place!

4016 Loft — Entire Modern Suite

Perfect for relatives visiting family! Designed to offer top tier comfort, in a safe & quiet neighborhood, so you can relax in style. Recently remodeled at 350 sq ft, the Loft perfectly accommodates single travelers, couples, & pets who can play in the shared fully fenced backyard! Remote work here is a breeze! Take use of high speed wi-fi, large built-in desk, & kitchenette stocked with coffee! Plus! Up your relaxation to the next level by reserving the HotTub amenity at $20/night!!

Scandinavian-Inspired Urban Farm with Sauna

Talo is a Finnish-style farmhouse bursting with creatively designed spaces and surrounded by a working urban farm. Unique amenities include a six-person barrel sauna, outdoor claw-foot tub, and a Solo Stove fire pit. It's also a 30-minute drive to Pawhuska and the Pioneer Woman's Mercantile, Tall Grass Prairie National Preserve, and the Osage Nation Museum. Talo is only minutes from downtown Bartlesville, home to Frank Lloyd Wright’s Price Tower and many great restaurant options.

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.

Backyard Bungalow

Historic carriage house converted into a tiny guest home, complete with everything needed for your stay. Full kitchen, washer and dryer, updated bathroom, quality mattress and entertainment center in a cozy space right next to downtown entertainment district. The historic Owen Park neighborhood is conveniently located within minutes of night life, restaurants, business, Gathering Place and Tulsa River Parks. The guest house is located at the back of a family home.

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.