Holiday houses in Jennings

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Top-rated holiday rentals in Jennings

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

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Top Guest favourite
The front view of the farmhouse features a green metal roof and a spacious porch with seating. The porch is enclosed by wooden railings and includes a small table. Lush greenery surrounds the house, enhancing its countryside charm.
Farm stay in Cushing
4.98 out of 5 average rating, 52 reviews

The Farmhouse Lovely 2 bedroom Fishing available

Relax with the whole family at this peaceful place to stay. Country living with abundant wildlife and catch and release watershed lake (no swimming). Plenty of wildlife photo opportunities. 11 miles north of Route 66 And 4 miles from Stroud Lake. 48 min. from Stillwater and Okla. State University, about an hour from Okla. City and Tulsa. Covered parking. No Smoking, Vaping, or marijuana use in the house. Want to craft? I have 2 Cricut machines and cartridges. I’m sorry we no longer allow pets.

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Guest favourite
Cabin in Sand Springs
5 out of 5 average rating, 11 reviews

Cabin in the Springs~Waterfront Access•Grand Deck

Cabin in the Springs is a peaceful 2BR retreat with pond views, a huge wraparound deck, and rocking chairs for slow mornings and quiet evenings. Fish the pond, watch the birds, and truly unplug. The king suite offers a jetted spa tub with separate shower and a cozy twin nook just off the primary; perfect for reading or kids. The guest BR also features its own ensuite. Set on an acre at the end of a quiet dead-end road… tucked away, yet minutes from town The Canyons golf course, and Osage Casino.

LocationComfortOutdoor spaces

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, 128 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!

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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
4.97 out of 5 average rating, 75 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.

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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, 142 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!”

FamilyValueIndoor spaces

Top Guest favourite
A single-story home is presented with a stylish front porch, framed by wooden railings. Large windows offer natural light, while a vibrant orange door serves as a focal point. The surrounding area features landscaping with rocks and bare trees, complemented by a clear blue sky.
Home in Perkins
5 out of 5 average rating, 142 reviews

The Roadrunner Modern 2 Bed Fully Furnished Home.

Be close to everything - conveniently located 1 block off main street - making it easy to plan your visit. Our smart enabled home features an open floor plan from the dining nook and coffee bar with a Kuerig, through the gally kitchen to the living room featuring roku tvs and comfy queen beds in each room , wifi, washer/dryer, privacy fenced area with gill and fire pit - the Roadrunner is fully eqipped with all the amenities of home for your stay. Private feel in a centrally located home.

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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
5 out of 5 average rating, 16 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.

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Guest favourite
Home in Cushing
4.88 out of 5 average rating, 8 reviews

Welcome to Cornerstone Villa LLC

Cornerstone Villa LLC, Welcome to our charming 3-bedroom 1 bath villa. Perfect blend of comfort convenience, providing an ideal escape for travelers seeking a memorable stay. Step inside and be greeted by a warm and inviting atmosphere. Sectional sofa and 65-inch smart TV to enjoy your favorite shows. Beautiful kitchen stainless steel appliances, and spacious counter tops. Laundry room/ sunroom 3 bedrooms- 1 King - 1 Queen- 2 Full beds. bathroom and shower tub combo. Wrap around porch.

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Top Guest favourite
Guesthouse in Mannford
4.96 out of 5 average rating, 24 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!

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Top Guest favourite
Farm stay in Cleveland
4.95 out of 5 average rating, 39 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.

ValueFamilyOutdoor spaces

Guest favourite
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
4.94 out of 5 average rating, 34 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!

ValueFamilyQuiet

Top Guest favourite
Guesthouse in Sapulpa
5 out of 5 average rating, 15 reviews

Guest House on the Farm

Escape to our newly built guest suite located on a charming two-acre hobby farm. We’re conveniently located just minutes from the highway, only a 10-minute drive to Sapulpa and about 20 minutes to Tulsa via the turnpike. A nearby lake, just 10 minutes away, offers kayaking, fishing, hiking, swimming, and boating. If you enjoy shopping and small-town charm, downtown Sapulpa features several unique local shops worth exploring.

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Popular amenities for Jennings holiday rentals

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