Family-friendly holiday rentals in Monkey Island

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

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.

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...

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 **

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.

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

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

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!

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.

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.

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.

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!