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

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

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Top guest favourite
A single-story lakeside home features a covered porch and large windows, providing ample natural light. The exterior is adorned in a blue hue, complemented by a well-manicured lawn. Steps lead up to the deck, where outdoor seating invites relaxation.
Home in Grove
4.94 out of 5 average rating, 48 reviews

Lakefront with Dock Access

This home has everything you need for the perfect lakeside retreat! Enjoy sunsets through the floor-to-ceiling windows or relaxing on the deck. Bring your boat and take advantage of dock tie-up access and 32-foot garage ideal for storage. Stay connected with high-speed internet and spend evenings gathered around the fire pit in the large backyard. Conveniently located just north of Wolf Creek Public Access, giving you quick and easy access to the water for fishing, boating, and lake adventures.

Top guest favourite
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
4.94 out of 5 average rating, 181 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 favourite
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 favourite
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 favourite
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, 157 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

Guest favourite
A well-appointed lakeside home is captured from an angled perspective, showcasing its stone and wood exterior. Large windows reflect the surrounding greenery, while a spacious deck extends toward the lake, providing access to views and outdoor relaxation.
Home in Eucha
4.83 out of 5 average rating, 12 reviews

Waterfront w/ Pvt Dock! 6 Bed/4 Bath, Sleeps 18!

Welcome to Grand Adventure, a property of Force Luxury Adventures! Whether you are looking for sun-filled days on the water or restful days to recharge, this perfectly situated home has it all. You can play in Drowning Creek, but have full lake view. Swim off our private dock, walk around the point, or go into town for dinner. If off-roading is your thing, we’re only 15 min. from Disney! From the minute you arrive, you will feel at home in this well-appointed house, stocked with you in mind.

Guest favourite
A cozy deck features a glass table with a central fire pit, surrounded by two dark chairs. The serene water view is framed by lush green trees and a clear blue sky, creating a tranquil setting for relaxation.
Cabin in Grove
4.91 out of 5 average rating, 115 reviews

On Waters Edge*Epic Lake Views*Couples*Modern Luxe

The VIEW on Grand. For the discerning traveler with high-end comfort in mind. Enjoy the incredible view while snug in bed. Sip coffee on the deck and watch the sun rise over the lake, roast marshmallows over the fire while listening to the sound of the water. Cozy up inside and watch the birds bob on the waves. Kayaks are stored on the side wall of Wren for our collective guests to enjoy. The stairs for lake access are immediately behind the deck and available for use by all eight cabins.

Top guest favourite
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, 60 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 favourite
An outdoor seating area features comfortable couches and chairs, arranged around a coffee table. A ceiling fan provides airflow in the shaded space, which overlooks the lake. The scene includes a clear view of the water and nearby decks.
Home in Eucha
4.97 out of 5 average rating, 102 reviews

So Grand Lakefront, Hot Tub, Dock & Game Room

With 5 BR, 2.5 BA, and endless outdoor decks, this Grand Lake waterfront property is perfect for large families. Located on South Grand Lake O' the Cherokees, you'll never want to leave! The direct open lake access, panoramic lake views and covered dock, will make you want to spend all your time in the sun, but with a garage bar game room, fire pit for s'more making and hot tub for relaxing while watching stunning sunsets, there is something for everyone. Good times are a guarantee!

Guest favourite
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
4.84 out of 5 average rating, 118 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 favourite
Home in Grove
5 out of 5 average rating, 17 reviews

Lakefront Hideaway | Boat Slip at Nearby Marina

Welcome to our cozy lakeside spot — it’s tucked away enough to feel like a getaway, but still right in town so everything’s close by. It’s a simple, peaceful place to relax. Grocery stores are just a few minutes away, and Wolf Creek Park is right down the road. You can sit out and watch wildlife or just enjoy the lake views from the porch. It’s a great place to slow down and breathe a little. We’ve also got a boat slip at local marina for you to use.

Guest favourite
A green lawn bordered by trees provides a spacious outdoor area. Several seating options are visible, including a pair of lounge chairs and a hammock. Two cornhole boards are set up on the grass, inviting leisurely games. Nearby structures offer a glimpse of additional outdoor living spaces.
Home in Grove
5 out of 5 average rating, 35 reviews

Lake Front Home on Grand Lake w/ Private Dock!

Relax with the entire family at this lakefront property in Grove, OK! Renovated 3-bedroom, 2-bathroom house with an open concept overlooking the lake just 10 minutes from main street Grove to enjoy coffee shops, grocery stores, and great local shopping. You can enjoy the large green space overlooking the water all day with seating areas under string lights, a private dock, covered parking, and plenty of sleeping options for the whole family.

Popular amenities for kayak rentals in Grand Lake O' the Cherokees