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 Hodge Lodge - Cabin with Ponds on 40 acres

This hilltop hideaway is perched 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 downtown Tulsa. Experience the best of both worlds thanks to the off-grid atmosphere and high-speed Wifi! One of five cabins on the property, the Hodge Lodge offers ample comfort, quirkiness, and opportunity to soak up the serene surroundings!

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!”

Pickleball | Hot Tub + Fire Pit | Downtown

Tucked in a quiet historic neighborhood, this guesthouse is your cozy retreat near Downtown Tulsa. Walking distance to vibrant local restaurants and shops on Cherry Street and The Gathering Place, America's #1 free park. After work or play, unwind in your private backyard - hot tub bubbling, firepit crackling, string lights overhead. Steps from lighted pickleball and tennis courts and walking trails, it’s perfect for couples, traveling nurses, or remote professionals to relax and recharge.

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!

Downtown Cottage by River Parks, Gathering Place

Detached cottage in historic downtown Tulsa neighborhood. Full kitchen, bed, desk, television room, shower, fenced patio with water feature, seating. One block from River Parks' cycling/walking trails, 3 parks; six blocks to The Gathering Place, walking distance to restaurants, bars, coffee shops. 1+ miles to BOK Center, downtown attractions & arts districts. Close to Route 66! Cozy and private retreat with patio, fenced area for pups and exceptional amenities!!

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!

Perfectly Located Cozy Apt Downtown, Gym Access

Newly renovated historic building in downtown Tulsa and close to everything! Walk across the street to the BOK Center, a few blocks from Cox Business Center, Cain’s Ballroom, Drillers Stadium, Brady Theatre, the Performing Arts Center..minutes from the Gathering Place, Utica Square Shopping, Cherry Street and River Parks. Only a 10min drive to the airport and the fairgrounds. All furnishings are West Elm. Washer/dryer inside the unit. Gym access

Cottage in the Country

Forget your worries in this spacious and serene space. Wide open spaces for kids and dogs to run! Quaint little country spot. 80 acres to take a walk, feed the goats, and enjoy yourself in a very laidback setting! This space is a guest house located directly behind a main residence. However the owner will respect your privacy and will not bother you. You have free access to walk, roam, hit golf balls and let your pets run.

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.

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.