Vacation rentals in Jennings

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Top-rated vacation rentals in Jennings

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Top guest favorite

Home in Cleveland

5 out of 5 average rating, 101 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!

Superhost

The Tiny House is nestled along the bank of a tranquil pond, surrounded by lush trees displaying autumn colors. A covered patio provides an inviting space, while a fire pit and grill area are visible nearby. Gravel and natural landscaping create a rustic outdoor setting.

Cabin in Sapulpa

4.77 out of 5 average rating, 142 reviews

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 downtown Tulsa. Experience the best of both worlds thanks to the off-grid atmosphere and high-speed Wifi! One of five cabins on the site, the Tiny House offers lots of opportunities for relaxation in a "tiny" package.

Top guest favorite

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

4.96 out of 5 average rating, 104 reviews

The Overlook @ Keystone Lake

Great getaway location! You will feel entirely to yourself. Room is "attached to house...but not "in" the 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 favorite

The exterior of Sparrow Cottage is shown, featuring a yellow building with green trim. A small flight of stairs leads to the entrance, surrounded by terraced landscaping. A fenced area with flowering plants and decorative elements is visible, alongside a small outdoor seating arrangement.

Guesthouse in Perkins

4.99 out of 5 average rating, 198 reviews

Private Cottage at the Old Station

Enjoy a piece of history while staying in the Old Station guest cottage. Comfy & cozy for two guests, or ideal for a personal retreat, "Sparrow Cottage" includes its own private patio with gas grill as well as a separate fenced sitting area outside with fire pit. Inside is a queen-size bed, a kitchenette (with sink, microwave, and mini-fridge), and a good-size bathroom with walk-in shower. Feel free to walk the grounds and imagine what the Old Station was like in the 1930s, 40s, and 50s.

Top guest favorite

A tranquil view of a cottage situated beside a small private lake, surrounded by lush greenery. The calm water reflects the natural scenery, while trees line the shore. The cottage features a wraparound porch, providing a serene and picturesque setting.

Tiny home in Ochelata

4.99 out of 5 average rating, 319 reviews

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.

Top guest favorite

A comfortable living area features a tan leather sofa with orange accent pillows and a matching chaise lounge. A wooden dining table with four chairs is visible. Light wood paneling and flooring contribute to a cozy, natural ambiance. A ceiling fan above offers airflow.

Cabin in Sperry

4.94 out of 5 average rating, 213 reviews

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.

Top guest favorite

A living area features an eclectic seating arrangement with a patterned armchair and a blue sofa. A coffee table holds a decorative arrangement of flowers. Natural light enters through dual doors, flanked by fabric blinds, creating a relaxed atmosphere.

Home in Bristow

4.99 out of 5 average rating, 107 reviews

Quiet Rt. 66 Guest House

Disconnect and take it easy at this unique, cozy getaway. Just one mile from the original 1920s Route 66, our remote private guest home offers the chance for travelers and city dwellers to recharge. Whether you're looking for a stopover on a Mother Road adventure or to get out of town and see the stars, this is the place for you. A full kitchen, washer/dryer and oversized shower add even more comfort. Perfect for your traveling pups with a fenced yard and dog door.

Guest favorite

An arched stone gateway leads to a charming cottage surrounded by lush green foliage. A pathway of irregular stone pavers winds through the landscape, inviting guests to explore the natural beauty of the property. A rustic stone chimney rises from the cottage, blending harmoniously with the surroundings.

Guesthouse in Tulsa

4.97 out of 5 average rating, 122 reviews

The Curious Little Cottage

This former 19th century stable hand quarters (Built in 1880) has been remodeled into a modern studio. Filled with curious tidbits, mind bending puzzles and unique creations it will provide a wonderful little cozy getaway. Tucked away in the back corner of the property you can enjoy the privacy of a cabin in the middle of town. Curious little cottage is only eight blocks from Tulsa Fairgrounds, minutes away from shopping downtown and the blue dome district.

Guest favorite

A large outdoor patio features a wooden deck surrounded by brick walls. Multiple seating arrangements consist of black chairs and tables, along with a central fire pit, creating a spacious area for gatherings and relaxation.

Place to stay in Stillwater

4.83 out of 5 average rating, 549 reviews

Cozy 2BR Private Farmhouse/Full bath/kit/Patio

Welcome to our Cozy Farmhouse on Main St. centrally located less than a mile from Boone Pickens Stadium. Enjoy Free Parking on Game Day and the Cozy Warmth of a 2 bedroom Farmhouse feel with a Large Outdoor Patio. Enjoy Tailgating with family and friends on game day with on our Large Patio, Grill, and Fire Pit. Also included on our Patio, is a Large 40,000 BTU Propane Gas Fire Pit to keep you warm on the cool Fall Football Games.

Top guest favorite

A cozy wooden hut features a welcoming porch with a wooden deck. A yellow chair is positioned beside the door, surrounded by greenery. Natural light filters through the trees, creating a warm atmosphere outside the hut.

Hut in Sand Springs

4.92 out of 5 average rating, 374 reviews

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.

Guest favorite

The exterior of the Carriage Loft studio is depicted, featuring a private entrance with a modern door and a window nearby. Soft outdoor lighting enhances the entrance, while greenery frames the space, giving a welcoming appearance.

Guesthouse in Tulsa

4.85 out of 5 average rating, 671 reviews

CARRIAGE LOFT -Historic Guesthouse Duplex Downtown

Superhost

A cabin is seen under a twilight sky, showcasing a deck with a hot tub. The horizon is illuminated by soft hues of orange and blue as the sun sets, creating a tranquil atmosphere around the property.

Farm stay in Jennings

4.81 out of 5 average rating, 185 reviews

[Lazy Spring] Star Gazing Sail Hot Tub

Welcome to our farm! Hear birds chirping and unwind in the hot tub. Enjoy the lovely setting of this romantic spot in nature. At night, turn off all lights in the cabin, and you will see the most beautiful and clearest stars, claim your stars in the hot tub or by the fire pit. Start your relaxing day with a self-made breakfast and a cup of tea/ coffee on our outdoor dining table on the deck.