Holiday houses in Osage

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Top-rated holiday rentals in Osage

Guests agree: these stays are highly rated for location, cleanliness and more.

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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, 129 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 wooden sign displaying 'Prairie's End' is mounted on two sturdy posts, surrounded by lush greenery. The natural wood finish complements the outdoor setting, inviting guests to enter the 40-acre property.
Home in Osage
4.98 out of 5 average rating, 82 reviews

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.

Top Guest favourite
A serene lake scene captures a vibrant sunset reflecting on the water, with silhouettes of trees along the shore. Gentle ripples create a shimmering effect, while varied cloud formations enhance the expansive sky filled with warm hues of orange, pink, and blue.
Place to stay in Cleveland
4.97 out of 5 average rating, 148 reviews

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!”

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, 551 reviews

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!

Guest favourite
The exterior of the home features a welcoming entrance with brick steps leading to a covered porch. A well-maintained lawn surrounds the property, which is accented by lush greenery and residential architecture. A tall antenna is visible, reaching toward a clear sky.
Home in Mannford
4.9 out of 5 average rating, 21 reviews

Old Waterslide Hill

Old Waterslide Hill is truly part of Mannford history. Centrally located in Mannford you're five minutes to New Mannford Ramp, ten minutes to Keystone State Park and right between Tulsa & Stillwater. You will be in the heart of this quiet little community. This cozy hillside home is fully remodeled & offers a spacious open floor plan, gorgeous woodburning granite fireplace and is fully furnished for your every need. Fishermen rest assured we have outdoor receptacles, water & ample parking.

Top Guest favourite
Guesthouse in Mannford
4.94 out of 5 average rating, 32 reviews

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!

Top Guest favourite
Farm stay in Cleveland
4.95 out of 5 average rating, 43 reviews

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.

Guest favourite
Home in Sand Springs
5.0 out of 5 average rating, 5 reviews

Keystone Lake Getaway

Escape to the peace of the countryside in this newly remodeled retreat near Keystone Ancient Forest and Keystone Lake. Surrounded by nature, rolling trees, and frequent deer sightings, this cozy getaway offers the perfect mix of comfort and tranquility. Relax in plush beds after a day of hiking, boating, or exploring the outdoors. Tucked away for privacy, yet located less than two miles from adventure and lake fun. Forget your worries in this spacious and serene space.

Top Guest favourite
Home in Sand Springs
5.0 out of 5 average rating, 24 reviews

The Splendid Sanctuary

Your Splendid Sanctuary awaits in this magical escape to the lake! Enjoy 3 acres of spacious land that ends directly at the shore’s edge. The Sanctuary is perfect for any type of getaway or adventure - laugher, rest & relaxation are yours. Large enough for a big family or just a couples getaway. Direct access to the lake provides for kayaking and camp fires at night. Grab some coffee and walk outside the back door and drop in your fishing pole.

Top Guest favourite
The living area features a charming combination of white cabinetry and soft furnishings, complemented by a stone fireplace and large windows allowing natural light. A dining table is set for six, and decorative floral arrangements add a touch of color throughout the space.
Guesthouse in Jenks
4.96 out of 5 average rating, 102 reviews

The Rose Cottage w/ Gardens & easy access to Tulsa

Charming and tranquil, this quaint Cottage is an enchanted haven where you can leave your cares behind. The Rose Cottage offers a wonderful retreat where you will feel rejuvenated, refreshed and renewed. Located close to restaurants and local attractions including the new Tulsa outlet mall located 1.5 miles away, with a grocery store just down the street. Check out all the amenities and come join us for a peaceful getaway.

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, 276 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
A modern farmhouse is set against a backdrop of lush greenery, featuring a covered porch and large windows. A gravel driveway leads to the entrance, framed by trees that provide shade, with an open field visible in the distance.
Home in Tulsa
4.99 out of 5 average rating, 256 reviews

The Scissortail Farmhouse - LAND, HOT TUB, horses!

Looking for a serene escape in a convenient location? The Scissortail Farmhouse is a home nestled on the edge of a working regenerative farm that supplies produce to many of Tulsa’s best local restaurants. It is minutes from the airport, downtown, the Gathering Place, zoo, and popular Tulsa attractions. We hope you enjoy our little slice of country that is about as close as you can get to the big city!

Popular amenities for Osage holiday rentals

  1. Airbnb
  2. United States
  3. Oklahoma
  4. Osage County
  5. Osage