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, 133 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, 87 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 winding path leads through an eclectic garden filled with various plants and artistic decorations. Distinctive garden pots, sculptures, and colorful ornaments can be seen throughout the area, creating a unique, inviting atmosphere surrounding the log cabin.
Cabin in Tulsa
4.98 out of 5 average rating, 319 reviews

An Artist's Cozy Log Cabin Minutes From Downtown.

Spend the night in a very Private, Cozy, Eclectic and Historically Imfamous Log Cabin, surrounded by an artist couple's one acre garden. Right by Downtown Tulsa! Located in Historic Owen Park Neighborhood. One of the oldest neighborhoods in Tulsa. Very close to The B.O.K. Arena, Tulsa Ball Park, Cain's Ballroom, Tulsa's Arts District, many restaurants, and the Tulsa Gathering Place. This Cozy cabin is perfect for a couple wanting a relaxing weekend and also a wonderful writer's retreat!

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
A covered porch space is highlighted by a colorful floral rug and a cozy seating area. String lights are hung above, enhancing the ambiance. A pathway lined with greenery leads to the outdoor area, while potted plants add a touch of nature.
Home in Stillwater
4.99 out of 5 average rating, 87 reviews

Pine & Feather

Pine & Feather is a boho cottage with vaulted ceilings, fireplaces, and fully equipped kitchen with a coffee bar. It features a primary suite with an en-suite bathroom, vintage clawfoot tub, and a cozy reading nook. The property has a covered porch with a grill and outdoor dining area, and is set on 3 private acres shared with the host’s home. Located just 5 minutes from downtown Stillwater and 10 minutes from Oklahoma State University, it’s a peaceful retreat with abundant wildlife.

Guest favorite
Guesthouse in Mannford
4.91 out of 5 average rating, 34 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, 46 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
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, 104 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.

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 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