Holiday rentals in Monkey Island

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Top-rated holiday rentals in Monkey Island

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Top guest favourite
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, 49 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 favourite
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, 106 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.

Guest favourite
Home in Afton
4.9 out of 5 average rating, 10 reviews

Lake Fever 14 Port Duncan Monkey Island Ok

MINS FROM BATTLEFIELD GOLF COURSE AND SHANGRI LA. Golfers delight minutes away from battlefield golf course five minutes away from Shangri-La clubhouse gated community. Port Duncan home is only four years old has been used as an Airbnb for golfers for the past few years people from all over the world come here to stay here quiet neighborhood you'll see deer Roaming the neighborhood at night time quiet peaceful, lots of opportunity for good dining experiences Lake within minutes away . Boat ramp

Guest favourite
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.
Apartment in Afton
4.91 out of 5 average rating, 68 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 **

Top guest favourite
Cabin in Afton
5 out of 5 average rating, 11 reviews

Grand Lake Waterfront Family&Friends Memory Maker

Tucked among towering trees, this cozy 2-bedroom, 2-bath cabin on Monkey Island sits on the shores of Grand Lake with WATER VIEWS FROM EVERY WINDOW! Newly refurbished and furnished. Sip coffee on the screened-in porch as lake breezes roll through; dine on the spacious back deck; unwind by the firepit; lounge on the seasonal swim dock. It’s the perfect blend of lakeside serenity and classic cabin charm for a truly relaxing getaway. Just minutes from renowned Shangri-La Resort. Pet Friendly.

Top guest favourite
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
4.98 out of 5 average rating, 109 reviews

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
Home in Afton
New place to stay

NEW Lake Retreat | Sleeps 12 | Pool + Fire Pit

Welcome to the Grand Escape — a gorgeous one-level retreat at Grand Lake featuring 4 bedrooms, 4 full bathrooms, 3 king suites, and a bunk room that sleeps 6 with an XBOX and Classic Arcade Games. Enjoy the community pool, incredible dock fishing, nearby golf, fire pit, complimentary s’mores, and beautiful lake views. Perfectly located within minutes from The Coves Golf Club, The Drunken Rooster- live music, food, playground, sand volleyball, Kahoots, and 20 minutes from Shangri-La.

Top guest favourite
A modern cabin stands among lush trees, showcasing large front windows that allow natural light to fill the interior. The wooden deck extends outward, providing a welcoming entryway. The surrounding forest enhances the cabin's sense of privacy and connection to nature.
Cabin in Afton
5 out of 5 average rating, 38 reviews

The Cabins of Horse Creek near Grand Lake in Okla.

Enjoy a stylish experience at our cabin in the woods. It has an open floor plan. We're just minutes away from lake fun on Grand Lake. Close to boating, shopping, and dining. We are on 22 acres with a creek for seasonal fishing, walking trail, fire pit for relaxing, and plenty of peace and quiet. We have a 50 amp RV spot available at extra cost for extra family. We have a couple kayaks we can launch. We live close by, so we will be available for any questions or needs you may have.

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, 120 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 favourite
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, 39 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.

Guest favourite
Home in Afton
5 out of 5 average rating, 8 reviews

Monkey Island Nautical Escape

Experience a relaxing stay at this newly updated 2 bedroom, 2.5 bathroom, townhome ideal for families or friend groups looking to relax and play. This home comfortably sleeps up to 8 guests. Spend your day on Grand Lake boating and fishing, or visiting Shangri- La Resort's golf course and many other amenities. The community boasts a swimming pool, basketball court and firepit and is walking distance to the Terra Miranda Marina and a short drive from a variety of restaurants.

Top guest favourite
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, 104 reviews

Twin Retreat Cabin 1:Hot Tub, Fire Pit, Golf, Boat

Welcome to The Twin Retreat: Cabin #1! Come experience a modern, rustic, yet luxurious 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, 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!

Popular amenities for Monkey Island holiday rentals