Vacation rentals in Jennings

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Top-rated vacation rentals in Jennings

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

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Top guest favorite
A welcoming guest house is accessed via a wooden deck surrounded by lush greenery. The entrance features a gabled roof and large front windows, inviting natural light into the space. Nearby, a large tree adds to the serene outdoor setting.
Guesthouse in Bristow
4.99 out of 5 average rating, 495 reviews

Historic Route 66 Guesthouse

Cozy guest house on historic Route 66 ideal for bikers, bicyclists, road trippers. Private entrance, access to secure backyard including available covered parking, hot tub, grill, fire pit, 1 king and 1 queen bed, private bathroom with small tub & shower, WiFi, TV, refrigerator, microwave. Within walking distance of large city park with fishing lake, golf course, disc golf, skatepark, tennis courts, & seasonal swimming pool. Kitchen not suitable for cooking but abundant local takeout available.

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, 131 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, 83 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 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
4.97 out of 5 average rating, 149 reviews

The Overlook @ Keystone Lake

Premier 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 spectacular 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!”

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
4.91 out of 5 average rating, 22 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
An aerial view captures a serene A-frame cabin with a sloped roof. A spacious wooden deck extends from the front, accompanied by a cozy fire pit area with surrounding seating. Lush greenery and a gravel path create a peaceful outdoor setting.
Cabin in Cleveland
4.92 out of 5 average rating, 39 reviews

Great lake views, luxury hot tub

Fun amenities: Luxury hot tub w/ blue tooth speaker, pool and ping pong table, wii gaming area, foosball table, ladder ball, disc golf hole, tree swing, fire pit, giant deck, bbq grill, smart tvs in every room. Serene, A frame cabin with stunning lake views only 20 minutes from downtown Tulsa. Watch the game on the 70' in the living room, unplug by the cozy firepit, or have a game night followed by some hot tub time. Nearby Pier 51 marina for easy boating! Superhosted by a local family.

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 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.

Top guest favorite
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 favorite
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 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 Sand Springs
5 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.

Guest favorite
Dome in Sand Springs
4.88 out of 5 average rating, 229 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.

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