Family-friendly holiday rentals in Monkey Island

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.

4.95 out of 5 average rating, 111 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.

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.

4.96 out of 5 average rating, 51 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

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.

5.0 out of 5 average rating, 21 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.

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.

4.82 out of 5 average rating, 95 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.

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, 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.

A two-story residence features a blue exterior with white trim and a brick façade. A garage door is prominently displayed, while the front yard is landscaped with grass. A streetlamp stands nearby, providing lighting for the walkway. The surrounding homes add to the neighborhood aesthetic.

5.0 out of 5 average rating, 9 reviews

Monkey Island Getaway

Relax & unwind in this charming 2 bedroom, 2.5 bath condo located on Monkey Island. You will have easy access to Tera Miranda Marina boat dock minutes from the door & a community pool, fire pit & fenced basketball court. You will have access to the 2 car garage which is equipped with a Tesla charger & trailer parking for your boat. Whether you’re planning a weekend retreat or an extended stay this peaceful escape offers all the comforts of home with the added perks of lake life

5.0 out of 5 average rating, 10 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.

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.

4.96 out of 5 average rating, 106 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!

A spacious living area is highlighted by a stone fireplace, surrounded by comfortable seating. Artwork adorns the walls, and a large mirror reflects the light. A coffee table sits in the center, while a view of the hallway and adjoining spaces is visible.

5.0 out of 5 average rating, 34 reviews

#MonkeyIslandHideaway at Grand Lake, Oklahoma

Incredible 5 bedroom waterfront home, minutes from Shangri La resort (golf, spa, and restaurants) on Monkey Island. Well appointed and spacious, perfect for entertaining any group. Steps away from boat slip at community dock and community pool, which is open seasonally. 4 bedrooms and 3 bathrooms on the main floor, and an additional upstairs living area/bunk room with private bath. Plenty of seating for meals and additional space on the back deck overlooking the water.

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.

4.98 out of 5 average rating, 113 reviews

Labor Day Deal! Bear Cabin on Monkey Island

Labor Day Special: Book the holiday weekend (Fri–Mon) and Thursday night is included at no extra cost. Message us if you’d like the extended stay and we’ll send a special offer. Escape to Bear Cabin on Monkey Island—perfect for golf trips, girls’/guys’ weekends, or group getaways. Relax in the private hot tub, enjoy indoor/outdoor fireplaces, cook in the full outdoor kitchen, or unwind on the spacious deck. Minutes from Monkey Island golf, Grand Lake, and The Anchor.

The modern home features large windows facing the lake, showcasing its expansive design. A spacious dock accommodates boats, with seating areas visible beneath a protective canopy. Surrounding greenery offers a natural backdrop, enhancing the serene setting by the water.

4.92 out of 5 average rating, 38 reviews

Waterfront home w/ private dock on Monkey Island

When you walk into this modern/industrial 4 bedroom home, the first thing you see is the lake through the back wall of windows and glass sliding doors. This unique place has a style all its own. Home is designed for indoor/outdoor living and gives you endless places to sit and enjoy the view. Back deck has a hot tub and grill and outdoor dining area. From the deck you easily access the dock down the ramp. Large dock has plenty of space for you to play all day.