Holiday rentals with a pool in Delaware County

The Hangout-Peaceful Ozark Hideaway

Your host has been on Naked and Afraid, so if you’re craving a rustic escape with comfort and character, this is it. Tucked away in the woods, this 3BR, 2BA cabin-style home sleeps 6+ & feels like staying at Grandma’s—simple, peaceful, & full of charm. Located in a quiet gated resort with trails, pools, golf, and river floats nearby. Close to Natural Falls, Fidler’s Bend, & Arrowhead Speedway. Perfect for families or couples wanting a slow-paced retreat. Not fancy—just cozy, clean, & welcoming.

Walk to Lake: Family Gem w/ Pool Access in Afton

Discover where worries meet their end and the fun begins when you visit Afton! This 3-bed, 3-bath vacation rental in The Reserve community puts adventure on land and on water within your reach. Walk to Grand Lake O' the Cherokees for endless water recreation, visit Royal Horse Ranch across the road for horseback riding and wine tasting, or make a splash at the community pool. When you're not checking off the vacation to-dos, spend downtime in this townhome featuring all of the comforts of home!

Luxury Resort Home - Stunning Clifftop Lake View

Luxury Clifftop Retreat at Grand Lake is spacious and perfect for the entire family. Perched high on a cliff, this stunning escape offers breathtaking views and frequent pelican sightings. 4 King BR | 4.5BA – Each with a private bath Infinity Pool – Feels like the Mediterranean Chef’s Kitchen – Perfect for entertaining 1 mile to popular dining, 2.5 miles to Cherokee Yacht Club Borders The Coves Golf Course F5-Rated Safe Room WiFi & High-End Amenities You won’t believe you’re in Oklahoma!

Pool & Outdoor Kitchen: Grand Lake Getaway!

Enjoy life on the lake as it was meant to be when you stay at this Grove vacation rental! With over 2,000 square feet of outdoor space, this 3-bedroom, 2-bath home is like your own resort! Spend your days lounging by the private pool, fishing or canoeing at Honey Creek State Park, or simply enjoying the million-dollar shoreline views. With easy access to Elk River Marina, a cozy fire pit, and incredible fall foliage opportunities, you'll find plenty to entertain you during fall!

#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, community pool, and private hot tub on deck. 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.

Rustic Red Barn No Cleaning Fee!

Luxury and rustic await you at Grand Lake. Nestled on the shores of a tranquil lake, the cozy Red Barn House exudes a magical charm that harmoniously blends rustic appeal with the serenity of waterfront living. The lake front is a mere 200 feet from the patio. The kitchen is a mix of delightful modern design and the living room boasts an open concept. Overall, the cozy Red Barn House is a charming and comfortable retreat that offers a unique living experience.

Grand Lake Midwestern fun

Situated on a peninsula in Grand Lake O' the Cherokees, an area known as Monkey Island in Northeast Oklahoma invites you to play on 60,000 acres of sparkling lakes and 1,300 miles of shoreline with every activity you can image in and out of the water. Club Wyndham Grand Lake's friendly Midwestern hospitality makes every generation feel right at home, from newlyweds to tiny tots to doting grandparents.

Waterfront 1 Bedroom/Cabin I/Newly Remodeled

Groveport Resort consists of 10 waterfront cabins. The property has 500+ ft. of shoreline, two boat docks, a boat launch, firepits, and a waterfront bar & grill. All of this in a protected cove on beautiful Grand Lake O' the Cherokees. We're also located within the city limits of Grove, Oklahoma near dining, shopping and attractions. the sounds of nature when you stay in this unique place.

Grand Lake 2 Bed/2 Bath Condo Resort ~Pool~Hot Tub

***Condo: spacious 2 bedroom/2 bath home (1,075 square feet) with a king bed in the master bedroom, two twin beds (request if you would like a Queen bed in the 2nd bedroom) in the guest room and one Murphy bed in the living room. Additional amenities include a full kitchen and dining area, fireplace, washer and dryer and balcony. Maximum occupancy is 6 people.