Vacation rentals in Jennings

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Top-rated vacation rentals in Jennings

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Top guest favorite
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, 134 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 favorite
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, 89 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.

Guest favorite
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
4.92 out of 5 average rating, 25 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 favorite
The single-story brick home features a spacious front yard with two mature trees. A well-maintained driveway leads to dual garages on the left side. Large windows with decorative treatments allow natural light to illuminate the welcoming entryway beneath a hipped roof.
Home in Mannford
5.0 out of 5 average rating, 15 reviews

Welcome to Keystone Sunrise

Enjoy fishing, boating, hiking, or just relaxing on the back patio that adjoins the corps land. Located in a small quiet neighborhood with lake access by golf cart or a short walk out the back door. A full service marina, floating restaurant, and boat ramp one mile away. The home has a split floor plan with private on suites for both guest bedrooms, a flex room for gaming/kids play or can sleep 2 guests with an air bed, and a spacious well equipped kitchen with a large dining table.

Guest favorite
Cabin in Cushing
4.85 out of 5 average rating, 27 reviews

New Country Cabin Fenced Yard

Country living in a secluded spot- newly built with custom cowboy/rustic features. Shaded fenced back yard, 3 bedrooms-2 full baths- one with walk in shower, one with shower/tub combo (huge tub) Twin Bunk beds, 2 Queen beds, Sofa recliners & 2 electric recliners, Parking in front. Covered front porch, Washer/Dryer, Salt Water filtration system, ceiling fans, 2 mini splits for heat and air. About 7 minutes from town on a gravel road. Access to television in all 3 bedrooms, and free Wifi.

Guest favorite
Guesthouse in Mannford
4.91 out of 5 average rating, 35 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 favorite
Farm stay in Cleveland
4.96 out of 5 average rating, 47 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.

Superhost
A rustic wooden cabin is showcased with a large covered front porch. The structure is surrounded by greenery, and outdoor seating is visible on the porch. The landscape is expansive, with a lawn in front that provides clear views of the cabin's inviting exterior.
Cabin in Cleveland
4.8 out of 5 average rating, 54 reviews

Lakersweekend Getaway 1/2 mile Appalachia Bay Area

1/2 mile to Appalachia Bay with boat ramp & ATV access. 5.5 miles to Keystone State park, 9.5 miles to Jellystone park. Plenty of parking for boats & ATV trailers. 2 bedrooms 1 with King Bed, 2nd bedroom Queen Bed. Bunk beds, futon, 2 loveseats with sleepers for extra guests in common living areas. 1 large shower room, 2 half bathrooms, fully stocked kitchen & dining. Full covered front porch with view of lake. Fire pit,charcoal grill, and swing set, corn hole game.

Guest favorite
A cozy living area features a black leather couch and a woven chair, complemented by a wooden coffee table. A decorative macramé hangs on the wall above, while a flat-screen TV is mounted nearby. Natural light illuminates the space, enhancing the inviting atmosphere.
Guesthouse in Mannford
4.95 out of 5 average rating, 38 reviews

Get-a-way guest house

This newly renovated Guesthouse is conveniently located just minutes from Keystone Lake. Formerly used as a tanning salon/boutique, now fit for a comfortable stay. Two queen bedrooms, one twin bedroom, and one pull out couch with linens and comforter in living area. Make some memories at this unique stay, set up for a couples get-a-way, a lake vacay, or a fun ladies/gents weekend. Featuring a Far Infrared sauna for complete relaxation. NOW OPEN FOR BOOKING!

Top guest favorite
Home in Cushing
4.93 out of 5 average rating, 14 reviews

Tatanka Run

Skip the hotel and enjoy more space for less! This remodeled 3-bedroom, 1-bath home is perfect for families, work trips, and weekend getaways. Relax in the cozy living room, cook in the updated kitchen, and enjoy the convenience of laundry and a versatile garage for parking or extra seating. Located less than a mile from downtown Cushing, 30 minutes from Stillwater, and about an hour from Tulsa and Oklahoma City. Your home away from home awaits!

Top guest favorite
Dome in Sand Springs
4.88 out of 5 average rating, 243 reviews

Geodesic Sunset Dome at Three Ponds Community

This cozy geodesic dome has its own private nook overlooking our second pond. 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 unique compost toilet for a truly memorable experience. Included in the dome is a mini fridge, microwave, Kuerig coffee, along with bowls, utensils, and towels.

Guest favorite
A charming outdoor view of a renovated house is framed by lush greenery and mulch. A gravel pathway leads to the entrance, while potted plants and seating areas enhance the inviting exterior. An American flag is displayed neatly by the front door.
Home in Blackburn
5.0 out of 5 average rating, 45 reviews

The Marlow Place Guest House

Come unplug and relax at this unique and tranquil getaway. Nestled in the woods on this historic property in a small little village in Green Country, it's the perfect place for refreshment and quality time away. Our little house is beautifully renovated and a great spot for viewing our resident fox, birds and deer or cozying up to read a good book.

Popular amenities for Jennings vacation rentals