Vacation rentals in Monkey Island

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Top-rated vacation rentals in Monkey Island

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Top guest favorite
A serene view of a green lawn is surrounded by tall trees, casting dappled shadows on the grass. In the background, a calm lake reflects the greenery, while a dock with boats is seen along the shore, enhancing the peaceful atmosphere.
Home in Afton
4.96 out of 5 average rating, 47 reviews

Grand Lake OK Monkey Island On the Water.

Enjoy this green woodsy area on Grand. A fairly quiet area on the lake. An entire acre to play in. There is room to set up for volleyball, badminton, or croquet in the front, so bring it with you. We have a fire pit both front and back set up. We have both youth and adult kayaks and cane poles for guests to use. It is an older building but we keep it up. This is also our families fun place and we are very happy to share it with our respectful guests . There should be an info book in the LR

Guest favorite
A modern cabin exterior is showcased, featuring wooden siding and large windows. A spacious deck with railing extends from the cabin, and a gravel path leads to a covered parking area. Lush greenery surrounds the property, enhancing its natural setting.
Cabin in Afton
4.95 out of 5 average rating, 97 reviews

Twin Retreat Cabin #2, Hot Tub, Near Golf Courses

Welcome to Twin Retreat – Cabin #2, your cozy getaway in the 94 West Community. This cabin sits right next door to Twin Retreat – Cabin #1, making it the perfect option for families or large groups who want to vacation together. Whether you’re planning a quick weekend escape or a long stay, Twin Retreat is designed for quality time, comfort, and convenience. You’ll be just minutes from Shangri La Golf Course & Resort/Spa, The Anchor Activity Center, nearby marinas, dining, and local attractions.

Top 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
4.94 out of 5 average rating, 180 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 spacious living area features a dark sectional sofa and a wooden coffee table atop a textured area rug. The kitchen showcases modern black cabinetry and stainless steel appliances, complemented by a breakfast bar with turquoise stools and warm pendant lighting.
Condo in Afton
4.9 out of 5 average rating, 63 reviews

Lofted Condo w/Golf Cart & Pool in Shangri La

Anchors Aweigh! Welcome to this beautiful condo in a gated community in Shangri La on Monkey Island on Grand Lake. You will be sure to find all the comforts of home for the whole family. Soak up the sun at the community pool or take a quick golf cart ride (available to rent!) to The Anchor where the kids can run wild. Enjoy a round of golf or one of the many bars and restaurants on Monkey Island. ** Click the ♡ on the upper right-hand corner so you can find us later and share us with others **

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, 150 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
A contemporary rustic cabin is nestled among mature trees, showcasing a spacious wrap-around deck. Large windows invite natural light into the interior, while a chimney rises above the structure, hinting at inviting warmth within.
Chalet in Afton
4.92 out of 5 average rating, 78 reviews

Hot tub, Shangri La 1mi, next to Battlefield Par 3

Welcome to The Highlander House! A contemporary rustic feel, nestled within the trees, allowing for privacy when using the hot tub or enjoying a meal on the wrap around patio. With room for nine, this place exudes comfort and peace, only yards from the lake. We're just past the brand new Battlefield Par 3 golf course, one mile from Shangri-La, walking distance to The Shebang restaurant & everything else at your fingertips. Golf, fishing, boating or simply reading a book; It's all here for you

Top guest favorite
Cabin in Grove
5 out of 5 average rating, 8 reviews

Lake front getaway w/slip located in Wolf Creek

Escape to this cozy one-bedroom, one-bath lakefront cabin with stunning views and modern comfort. Minutes from Wolf Creek boat ramp, dining, and downtown Grove, it’s the perfect blend of privacy and convenience. Enjoy lake views from the living room, coffee on the screened porch, and sunset evenings by the fire pit. With shared dock access, boat slip, and concrete parking, it’s ideal for boating, fishing, or simply relaxing by the water—perfect for couples, families, or tournament stays.

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
4.84 out of 5 average rating, 116 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.

Top 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, 96 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, 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!

Top guest favorite
A hot tub is situated beneath a wooden overhang, surrounded by large windows that invite natural light. Comfortable wicker seating is arranged nearby, offering an inviting space for relaxation. The outdoor kitchen area is partially visible, enhancing the outdoor entertainment setting.
Home in Afton
4.91 out of 5 average rating, 66 reviews

Heartland Haven: Hot Tub - Game Room - Basketball

Welcome to Heartland Haven! With 11 beds and 3 full baths there's plenty of space for everyone. Outdoor entertainment is the theme at Heartland Haven with HOT TUB, basketball court, outdoor kitchen, fire pit & lake views! If the weather isn't cooperating, don't fret, we have a covered back patio that allows you to enjoy the outdoors regardless of weather. We also have an arcade game, board games, foosball, smart TVs and plenty of cozy accommodations indoors!

Top guest favorite
The cabin features a spacious wooden deck with a pergola, surrounded by trees displaying autumn foliage. The exterior walls are painted in a light blue hue, and a chimney rises from the roof. A seating area is visible on the deck, complementing the inviting outdoor space.
Cottage in Afton
4.97 out of 5 average rating, 207 reviews

Lake waterfront, dock parking, private launch

Parking is very limited so please take note! Lakefront studio cabin in Padley’s Point! This cabin has a fully furnished kitchen and still has that cottage (one big room) charm. The bedroom area has a queen over queen bunk-bed that comfortably sleeps 4. Property is located 5 feet from a private launching ramp and private dock. Lakeside fun is just steps away! Swimming, fishing, and boating can be enjoyed from your private nautical oasi

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