Vacation rentals with a kayak in Grand Lake O' the Cherokees

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Top-rated kayak rentals in Grand Lake O' the Cherokees

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Guest favorite
A warm gathering space showcases floor-to-ceiling windows that reveal serene lake views. A cozy fireplace, framed by original cedar walls, enhances the inviting atmosphere. Outside, a private dock leads to the calm waters, while a fire pit area encourages evening gatherings.
Home in Disney
4.96 out of 5 average rating, 48 reviews

Disney Wateredge Retreat-Private Beach & Dock-Sout

Over 3,000 square feet of fun! Whether you plan to boat, ride off-road trails or just relax, Disney Wateredge Retreat on Grand Lake O' the Cherokees is the perfect blend of fun and relaxation, right on the water. This renovated 1970's chalet features floor to ceiling windows, and 5 bedrooms, most with a lake view. Area roads permit golf carts & UTVs. Boat & UTV rentals are minutes away, and great restaurants are all very convenient. Please, no animals permitted due to vintage wood plank floors.

Guest favorite
A serene lake view features a calm water surface reflecting soft pastel colors of a sunset. Several docks extend into the water, accompanied by lush greenery lining the shore. The peaceful landscape invites relaxation amidst the natural beauty.
Home in Eucha
4.95 out of 5 average rating, 170 reviews

Spectacular Waterfront Luxury w/dock Grand Lake!!!

Click [♡ Save] button to easily find this listing again before your dates are booked. Enjoy the wide-open lake views! Wake up in a luxurious lakefront home peacefully enjoying a cup of coffee. From the balcony hear birds singing and boats humming. You will fall in love with the view and privacy of being so high up, but so close to your own private dock below. As the sun sets catch up with friends by the fire. Then fall asleep watching the stars from bed as light dances on the water below...

Guest favorite
A serene lakeside view is presented at dusk, featuring a wooden dock extending into calm waters. Soft reflections of illuminated buildings can be seen along the shoreline, with scattered clouds in the twilight sky creating a tranquil atmosphere.
Cabin in Wyandotte
4.88 out of 5 average rating, 105 reviews

Grand Lake Fishing Cabin *Dock/Ramp *late checkout

Welcome to the Best Little Grand Lake "Fishin' Cabin"! *Late checkout (bc we know you won’t want to leave)* Located in one of THE best spots on the lake for fishing, boating, catching sunsets, etc... there is a reason this area is named Paradise Point! You will be as content as can be in our lakefront, humble, cinderblock cabin. Completely remodeled & decorated to be quaint & comfortable. Enjoy your private dock, large deck and access to our boat ramp…or play poker in the large 3 season porch.

Guest favorite
A serene sunset is captured over Grand Lake, with the sun reflecting on the water's surface. Docked boats are visible in the marina, framed by trees, creating a peaceful ambiance. The structure's windows enhance the view of the tranquil setting.
Home in Afton
5 out of 5 average rating, 13 reviews

Waterfront Private Dock Monkey Island!

Welcome to your dream vacation on Grand Lake! Our luxury waterfront property on Monkey Island has a private dock and stunning lake views. The Island features vibrant nightlife, dining, and the Shangri-La resort. This vacation home feels like a true retreat with a fully stocked kitchen, wet bar, coffee bar, pool table, & ping pong. Our cove is ideal for swimming & fishing, with a neighborhood boat ramp & several nearby marinas. Comfortably sleeps 8 with spacious rooms & well-appointed bathrooms.

Top guest favorite
A charming cottage sits beside a tranquil spring-fed pond, featuring a large deck accessible from the rear. A fire pit resides in the grassy area, with lush green trees surrounding the property, enhancing the peaceful outdoor setting.
Cottage in Eucha
4.99 out of 5 average rating, 145 reviews

Private Spring Fed Reservoir w/paddle boat

Off the beaten path, approximately 1 mile down a bumpy dirty road you will find a hidden gem. At the edge of the Ozarks in the heart of green country is a small cottage located on a beautiful one acre spring feed pond. You can see the spring gushing out of the hillside. Our cottage is small, cozy, and very relaxing. Whether you are kicking back watching the tube or paddling around the pond you will feel right at home and may not want to leave. Paddle boat, 4 paddle boards and 2 kayaks included

Top guest favorite
The silo structure is showcased against a vibrant sunset, with clouds reflecting shades of orange and pink. The grassy area in the foreground leads to a gravel driveway, while the building features a covered porch, inviting views of the surrounding landscape.
Barn in Vinita
4.98 out of 5 average rating, 43 reviews

Harvest Hill Silo- Route 66 Home w/ Fishing Pond

Setting on Route 66, just 2 miles from I44 Vinita exit, the silo is situated on 20acres and includes a stocked 5 acre pond for fishing and exploring! The bin has a full kitchen and a custom tiled shower in the downstairs bathroom. Downstairs also has a bedroom with a queen bed as well as a full size pull out. Upstairs has 1 bedroom with a twin over full bunk bed, 1/2 bath and a second living room with a queen size pullout. Enjoy the sunset or sunrise over looking cattle and horse pastures.

Guest favorite
A coffee mug rests on a wooden railing, overlooking a tranquil waterfront scene. A private dock is visible, with people enjoying the outdoors under a canopy of lush green trees. Sunlight filters through the foliage, creating a peaceful atmosphere.
Cottage in Grove
4.84 out of 5 average rating, 88 reviews

The Cottage At Grand Lake

Cozy retreat. This beautifully decorated, 2-level, 2-bedroom cottage sleeps up to 9, with a private dock nestled in Fisherman's Cove on North Grand Lake. Perfect balcony for relaxing, grilling out, and taking in nature. Ideal for a family retreat, girls' weekend, a couple's getaway, or a fisherman's refuge. Upstairs, king bedroom. Downstairs, two full beds, plus one set of bunkbeds and a single trundle. **Please see "Safety & Property" section of the listing, regarding small children.

Guest favorite
A cozy two-story home is nestled among trees, featuring a spacious deck with seating and direct access to the water. A pair of kayaks is positioned next to the deck, while a wicker chair adds a comfortable touch to the surrounding landscape.
Home in Afton
4.94 out of 5 average rating, 49 reviews

Waterfront Getaway! Fish from a Private Dock!

Book "The Lucky Duck" - your destination to a fun and tranquil escape! Nestled by Grand Lake, this cozy waterfront spot is the ultimate playground for families or an ideal retreat for romantic couples! Located on Duck Creek, you'll never want to leave! With direct access to the lake, water views, a cozy dock, a deck that wraps around like a hug, a s'mores-worthy fire pit, and endless spots to kick back, this place is a chill paradise for all!. Get ready for a blast of fun guaranteed!

Guest favorite
The exterior of the cabin showcases a blend of wood and stone materials, highlighted by a large deck featuring outdoor seating and a hot tub. Surrounded by trees, the cabin offers a serene setting with ample natural light filtering through large windows.
Cabin in Afton
4.96 out of 5 average rating, 90 reviews

Twin Retreat Cabin 1:Hot Tub, Fire Pit, Golf, Boat

Welcome to The Twin Retreat: Cabin #1! Come experience a modern, rustic, yet luxury stay in our meticulously furnished cabin! With the private hot tub, stone firepit, kayaks, games and cozy furniture, you won't want to leave. If you decide to venture out though, the cabin is perfectly situated just 1 mile from Shangri La Golf Courses and Resort/Spa, the new Battlefield Par 3 course, & the Anchor Activity Center. Whether you seek adventure or rest, we look forward to hosting you soon!

Guest favorite
A cozy lakehouse is seen with a covered front porch featuring outdoor seating. Planters with blooming flowers are positioned along the base. The entrance is highlighted by a welcoming yellow door, and lush trees provide shade around the property.
Home in Afton
4.83 out of 5 average rating, 115 reviews

Calhoun lakehouse on Monkey Island w/Golf Cart opt

Come relax at this peaceful, cozy lakehouse in the heart of Monkey Island. Golf cart available to rent. 1 kayak available to use. Launch your boat across the street at the private ramp & take advantage of the opportunity to fish in "The Crappie Capitol of the World" Golfers, the award winning Shangri la golf course & par 3 Battle Field are less than 1 mile away. Welcome small dogs for fee. Enjoy the nearby night life entertainment, restaurants, & golf/walking and cart trails.

Guest favorite
A spacious living area features a large sectional sofa adorned with decorative pillows. Exposed wooden beams stretch across the ceiling, while a flat-screen television is mounted above a cozy fireplace. A rustic coffee table sits atop a patterned area rug, enhancing the warmth of the space.
Bungalow in Jay
4.97 out of 5 average rating, 69 reviews

Cozy Cove Bungalow at Grand Lake

Relax with the whole family at this peaceful treehouse bungalow. Five bedroom house with large back deck that expands the entire house with breath taking views of Grand Lake. We are the last house in the back of the cove, offering a true secluded getaway. Swim off the swim deck, build a fire, kayak, or challenge family and friends to a game of foosball or ping pong! Upstairs garage apartment has a kitchen, queen, and a pull out sofa. This can be rented for an additional $100.

Top guest favorite
An aerial view captures the property set on a spacious lot by the water's edge, surrounded by lush greenery. A private dock extends into the lake, offering a swim deck. The warm light from the house's windows contrasts with the evening sky, creating a serene atmosphere.
Home in Vinita
4.95 out of 5 average rating, 64 reviews

Newly Renovated Modern Lakefront House on 1 Acre

Bring your family or friends for a Grand Lake O’ the Cherokees vacation featuring some of the best lake views in the state. This roomy, newly renovated, 4 bed, 2.5 bath stylish lakefront home nestled on a 1 acre lot in the woods of the Ozark foothills is about as close as you can get from the OKC or Tulsa area. Over 100 ft of lake frontage includes a private partially covered dock with swim deck and jet ski lift as well as hot tub in this private Grand Lake oasis!

Popular amenities for Grand Lake O' the Cherokees kayak rentals