Vacation rentals in Monkey Island

4.95 out of 5 average rating, 101 reviews

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

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.

4.9 out of 5 average rating, 63 reviews

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

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 **

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.

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.

4.98 out of 5 average rating, 174 reviews

Nanny's Guesthouse near Grand Lake, Grove, OK

Charming and comfy, this recently updated three bedroom home features open spaces, a full kitchen, private drive, back patio & grill, and plenty of parking. It is minutes from Grand Lake and 10/15 mins. from local restaurants, shopping, and local movie theater. The closest boat ramp is 7 miles. We are 5 mins from Grand Lake Casino and 15 mins. from Shangri-La Resort & Golf course. Nearest airport: Tulsa~ 78 miles Joplin, MO~45 miles Check us out/leave a comment on Facebook @Nannysguesthouse

4.98 out of 5 average rating, 103 reviews

A modern rustic cabin is presented with a wooden exterior and large, expansive windows. A spacious wrap-around deck enhances outdoor access, while the surrounding greenery provides a natural setting. The structure showcases a blend of contemporary design and rustic charm.

Cabin in Afton

Bear Cabin with Hot Tub & Fire Pit

Escape to Bear Cabin on Monkey Island — perfect for golf trips, girls’/guys' weekends, or group getaways. Relax in the private hot tub, gather by indoor/outdoor fireplaces, or cook in the full outdoor kitchen with grill & smoker. Enjoy evenings around the fire pit under the stars or unwind on the spacious, group-friendly deck. Modern-rustic cabin just minutes from Monkey Island golf, Grand Lake, and The Anchor. Weekly summer stays encouraged — plan early for holidays & prime summer weeks!

Superhost

A spacious lakefront home is nestled among mature oak trees, offering a peaceful setting. The exterior features a light-colored facade with a welcoming entrance and multiple garage doors. The lush green lawn leads toward Grand Lake, visible in the distance beyond the trees.

4.76 out of 5 average rating, 21 reviews

Monkey Island Waterfront House with Hot Tub & Dock

Lakefront home with private boat dock on Grand Lake in a magnificent location surrounded by all Monkey Island has to offer! Roast marshmallows at your lakeside fire pit or enjoy the view of your 250' shoreline from the large windows. Amid 2.5 acres of mature oak trees and with 3200 sq. ft. of open plan space, this home offers an idyllic setting for your lake house escape no matter the weather. The fenced back yard is perfect for families with small children who want a house on the water.

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.

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.

A serene bedroom is presented with a spacious bed layered in neutral-toned bedding, complemented by decorative pillows. Two bedside lamps provide soft illumination, and a ceiling fan circulates air. A tapestry hangs above the bed, adding texture to the wall.

5 out of 5 average rating, 36 reviews

Monkey Island Casita, A Grand Getaway!

Explore Grand Lake o’ the Cherokees at this central spot near all the fun! This bright and cozy home features an open kitchen and family room, as well as a cheery sunroom with large dining table for gatherings or morning coffee. Close to everything Grand Lake has to offer, including Shangri-la Resort, golf courses, and great restaurants all accessible by the 5 mile golf cart path. Bring your own boat and utilize the neighborhood ramp or rent one at the many local marinas nearby.

4.96 out of 5 average rating, 97 reviews

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

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!

The exterior of the house is presented with large windows and decks, offering views of the surrounding greenery and lake. A spacious yard is visible, adorned with natural landscaping and stone pathways leading to the entrance. The scene is set against a colorful sunset sky.

4.9 out of 5 average rating, 122 reviews

The Beach House at Grand Lake

Welcome to the Beach House at Grand Lake. If you are looking to stay at a peaceful location with a private dock (excluding the use of boat slip) and a great view, you've come to the right place. You can relax inside next to a cozy fire or enjoy the outdoors on our private deck. You will have an amazing view inside and outside, of Duck Creek and the main lake. You can enjoy fishing and floating off the dock or just lounging with your feet in the water. Amazing sunrises!

4.97 out of 5 average rating, 211 reviews

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

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

A cozy bedroom features a spacious bed adorned with a navy blue and white blanket. Natural light filters through a window, highlighting the room's neutral tones. A framed dog print adds character to the wall, complementing the modern furnishings.