Vacation rentals in Monkey Island, Oklahoma

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Monkey Island, Oklahoma

Guests agree: these stays are highly rated for location, cleanliness, and more.

%{current} / %{total}1 / 1
Top guest favorite
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 Monkey Island
4.98 out of 5 average rating, 95 reviews

Bear Cabin>Golf Retreat~Lake~Hot tub~Fire pit

Escape to our modern, rustic cabin on Monkey Island at 94 West for a perfect lakeside getaway. Spend your days walking the nearby Monkey Island Trail, enjoying lake activities, playing golf on one of the many Shangri-La courses, and food and family fun at The Anchor. Come back to relax in our hot tub or cook dinner on the grill. Our cozy cabin boasts all the modern amenities you need for a comfortable stay, while still retaining its rustic charm. Book now and enjoy the perfect lakeside retreat!

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 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, 44 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!

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

Superhost
A spacious living area features a comfortable couch and a stylish coffee table. Large windows allow natural light to fill the room, which is accented by a ceiling fan. A dining space with a table and chairs is visible in the background.
Cabin in Afton
4.87 out of 5 average rating, 83 reviews

The Deckhouse-Monkey Island Getaway

Relax and unwind after a day of exploring Grand Lake and all that it has to offer here at “The Deckhouse”. Enjoy the fire pit, play some shuffleboard or corn hole, or watch a movie on one of the 3 smart TV’s. Only 3.5 miles from Shangri La Resort, golf courses, marinas and restaurants are within 5 miles. We have games, toys, kid-sized table with 2 chairs, and a Nintendo Wii console/Wii sports for the kiddos. There is a private neighborhood boat loading zone just steps away. Pet-friendly.

Guest favorite
A modern A-frame cabin showcases a striking triangular design with large glass windows reaching toward the peak of the roof. The entrance features a dark facade with subtle landscaping, situated among lush greenery and nature. A wooden walkway leads to the door, connecting the cabin to the surroundings.
Cabin in Wyandotte
4.87 out of 5 average rating, 30 reviews

A Frames on Paradise Bluffs - #1 (of 3)

Brand new A Frame with balcony overlooking Grand Lake. Located on a serene 115 acres on Paradise Bluffs. Take a short trail to the rocky waters edge, explore trails on the acreage (bring your ATV or walk them), watch the Eagles fly, congregate around the fire pit, play a game of horse shoes, hire a fishing guide (best area for fishing!!), hit the nearby casino’s, enjoy the amazing sunsets and relax in our little slice of heaven. This is #1 of 3 cabins side by side. Message me about #2 & #3

Top 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, 91 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
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
4.84 out of 5 average rating, 114 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
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.
Home in Afton
5 out of 5 average rating, 35 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.

Top guest favorite
An A-frame structure is illuminated against a twilight sky, displaying large windows that showcase a warm glow inside. A stone patio surrounds a fire pit, with flames flickering, complementing the natural outdoor setting. Trees frame the scene, adding to the secluded ambiance.
Place to stay in Afton
4.91 out of 5 average rating, 35 reviews

The Aurora Aframe @ Selena Vista

Enjoy the lovely setting of this romantic spot in nature. This Aframe is secluded with a beautiful lakefront view. Deer, horses, foxes and an array of birds can be seen from the front porch. Covered porch and stone patio with a fire pit and chiminea are available. Hot tub for two, and outdoor grill are available for cookouts. This is the perfect spot to get away from the city. You will never believe that you are on Grand Lake. The sunsets are incredible.

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, 201 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

Popular amenities for Monkey Island, Oklahoma vacation rentals