Vacation rentals in Monkey Island

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Top-rated vacation rentals in Monkey Island

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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, 104 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.

Top guest favorite
A cozy living area features a gray sectional sofa with decorative pillows, paired with a simple coffee table. A compact kitchenette with glass-front cabinets is visible, along with a bear sculpture adding a rustic touch. Neutral-toned walls and carpet contribute to a calm environment.
Barn in Afton
4.98 out of 5 average rating, 43 reviews

Monkey Island Caddyshack

Welcome to Grand Lake O’ the Cherokees! Enjoy a stay in a rustic barndominium on the one & only Monkey Island where you’re only a golf cart ride away from bars, restaurants, Shangri-La Resort & Golf Club and more. You’ll find easy access to the lake with a public boat ramp only 100yds away. Whether you’re looking for a peaceful weekend getaway, to take advantage of world renowned fishing & golf, or enjoy being on the lake with family & friends, you’re bound to make memories you’ll never forget!

Guest favorite
An aerial view showcases the multi-story condominium surrounded by lush greenery and a championship golf course. Blue waters of the lake reflect the sky, while winding pathways and manicured lawns create a harmonious outdoor setting.
Condo in Afton
4.94 out of 5 average rating, 54 reviews

Unbeatable Location: golf course view sleeps 6

Relax in this 2 bed/2 bath condo overlooking the championship golf course at the Shangri-La Golf Club. You will enjoy sitting on the private balcony and enjoying the peaceful view while drinking your morning coffee. You will be minutes away from the Battlefield par 3 course, a short walk to the Shangri-La resort, the Anchor activity park, or you can take part in the many activities along the shoreline of Grand Lake. Perfect for solo trips, families, couples retreats, girls' weekends, and more!

Top guest favorite
The exterior of the Monkey Island Shack Outback is showcased, featuring a rustic wooden façade with a red door. The property is surrounded by lush greenery, and a spacious driveway leads up to the front porch, which is accented by wooden columns.
Cabin in Afton
5 out of 5 average rating, 33 reviews

Cabin with Big Shop & RV hookup! Bring your toys!

The Monkey Island Shack Outback is conveniently located at the intersection of highway 85A & OK 125 S, less than 10 min from Shangra La and less than 15 min from Grove, OK and the Wolf creek boat ramp. There are plenty of gas and food options as well as a family dollar and a dollar general, all within walking distance. There are multiple boat ramps less than 5 min away. Whether its lake fun with family & friends, tournament fishing, or somewhere to park your RV and stay awhile, this is it!

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, 143 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 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
4.94 out of 5 average rating, 89 reviews

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

Welcome to the Twin Retreat - Cabin #2 located in the 94 West Community. Our sister cabin (Twin Retreat Cabin #1) is located right next door, which allows both cabins to be booked together for larger gatherings. A place for families and friends to vacation for a few days or a few weeks together. The cabin is located just minutes from Shangri La Golf Course and Resort/Spa, The Anchor Activity Center, marinas, dining, and much more. Your family will be close to everything when you stay here.

Guest favorite
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
4.92 out of 5 average rating, 107 reviews

'The View on Grand' Epic Lake Views*Modern Luxury

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.

Guest favorite
The image depicts a cozy sleeping area with two single beds adorned with white linens and purple accents. A framed artwork featuring grapes is mounted on a textured dark wall. A bedside lamp stands next to one bed, and a light-colored chair is positioned nearby.
Cottage in Afton
4.93 out of 5 average rating, 216 reviews

Monkey Island Winery and Cottages #1, Cabernet

Our three cottages built in 2017 are on a 65 acre Horse Ranch with a Winery and Vineyard. Each sleeps up to six and are very private. Second bedroom is a loft built over the bathroom , 54" ceiling peak designed for kids but adults enjoy the space with two single beds and is open to the main floor. Located on Monkey Island, Grand Lake, Oklahoma. Pets are always welcome at Monkey Island Cottages with no additional up-front fee. A "house" is needed if the pet is left alone in the Cottage.

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
4.95 out of 5 average rating, 87 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
4.84 out of 5 average rating, 111 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 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, 200 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

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, 165 reviews

Spectacular Waterfront Luxury w/dock Grand Lake!!!

Enjoy the wide open lake views!! Either from the comfort of the beautiful living room, while preparing a meal at the kitchen or while enjoying it at dinner, you will have the most astonishing lake views from this beautiful house. On the fall and winter wake up to eagles in flight. This jewel is located at the main lake and close to lakeside restaurants and a marina for boat launching. This beautiful house was just built and is ready!!!

Popular amenities for Monkey Island vacation rentals