Holiday rentals in Olean

Views for Miles, Balconies, Billiards, Arcade, Bar

Escape to Sunset Bluff, where panoramic views of the Osage River and Osage National Golf Course fill every room and three private balconies. Challenge friends to billiards, shuffleboard, and arcade games, gather around the custom fire pit, and enjoy meals from the fully stocked kitchen or outdoor grill. Only 13 minutes from Bagnell Dam, Backwater Jacks, beaches, boating, shopping, dining, nightlife, and family attractions await! Perfect for families, friends, reunions, and relaxing together!!!!!

Willow Acres

Willow Acres Luxury Barndo on 32.5 is a perfect blend of stylish rustic vibes & wide-open space. Great for a getaways , family time & events. 🛌 What You’ll Love: • Spacious bedrooms • Stocked kitchen • Wraparound patio • Trails & private pond 🌿 Space to Breathe: See deer at dusk, enjoy a picnic by the pond, morning coffee, sunset wine & more! 📍 Close to It All: • 15 minutes from Osage Beach for lake life • 30 minutes from Jefferson City • Minutes from Eldon for groceries, & dining

Restored cottage built in 1906 (2 bed/2 bath)

Looking for a nice place to stay close to Jeff City? Spend a few nights in this restored cottage built in 1906! You are sure to be comfortable in this great little hideaway! The cottage has period appropriate furnishings with all the modern amenities! This historic property is located on a quiet street near an elementary school. California is a great location. We are an easy 25 minute drive to downtown Jefferson City and situated halfway between St. Louis and Kansas City right off Highway 50!

Rocky Creek Hideaway

If you need to get away from everything and need some peace and quiet this is the place for you. This house is nestled back in the woods, It has a dry creek in the back yard and also has a pond. It is in a rough gravel road, the wildlife roam freely around this place. The drive way is around 1/4 mile long. It is only 6 min from Versailles. 17 min to the closest lake Ozark access, and only 12 min to the Loop 2 Relax with the whole family at this peaceful place to stay. No Tv, but do have WI-FI

Lakescape Romantic Retreat w/ Hammock - No steps!

"This is IT!" 3mm Million Dollar Main Channel Panoramic View, Walk-in Level Entry, Two 58" Roku TV's, King Sized Bed, Electric Fireplace, Screened-in Deck, Electric Blackstone Griddle, Salt-water Pool, Deck Furniture, Papasan Lounger, Keurig Coffee, 400mbps WiFi... and a hammock! The perfect retreat for couples, but big enough for a small family... we'd love to host you at Lakescape Romantic Retreat! We believe our condo checks so many boxes that you'll say, just like we did, "This is IT!"

Lake Ozarks! New Vacation Condo on the Strip-C

Welcome to Paradise City Unit C! The ONLY Nightly rentals on the HISTORIC Bagnell Dam Strip! Brand new 3 bed 2 bath vacation rental condos on the strip. Everything is brand new, fresh, clean and stylish. This unit can sleep up to 10. Enjoy the night life, car shows, boat shows, boat races, bike fest and everything else that this area has to offer! There are boat rentals, parasailing and jet ski rentals just steps from this unit. Close to shopping, entertainment, restaurants and more! .

Bird's Nest: Western-view A-frame, private dock

No matter the season, no matter the reason, this all-season A-frame is built to deliver. Fish in deep water, read in the cozy loft, go gourmet in the fully-equipped kitchen, grab some floaties and float in the waves the boats make in summer, or sit on the dock and listen to the wildlife in the off-seasons. Two porches off the house and an over-water martini deck provide ample opportunities for taking in the views, and each comfortable, stylish room boasts a sunset view of the water.

Emerald A Lakefront w/ Hot Tub

Welcome to our Lakefront Oasis at the beautiful Lake Ozark! Experience the epitome of lakeside in our stunning, stylishly decorated house that's perfect for four guests. Nestled on the serene shores of the Lake of the Ozarks, this tranquil retreat promises an unforgettable getaway. Whether you're seeking a romantic escape or a family-friendly vacation, our Lakefront Oasis offers the ideal setting to create lasting memories. Take advantage of our boat slip and bring your boat along!

The Highland Bin at Haywire Acres, Highland Cows

Welcome to our charming boho-inspired Grain Bin Cabin, the Highland is ideal for 2-3 adults or 2 adults and 2 smaller children. Upstairs, you'll find a comfortable king bed in the loft, while downstairs features a cozy futon in the main living space. The full kitchen is equipped with everything you need. Full Bath with a walk-in shower downstairs. Experience a serene countryside getaway with breathtaking sunsets and peaceful surroundings, just moments away from Versailles.

Lakefront Home on the Point

Home built in 2021 with all amenities you could want. Spacious living areas, great for families or groups - private baths for each bedroom and plenty of dining and outdoor space for fun and entertainment. Outdoor fire pits on the point and patio. A very unique property sitting on a point with incredible views onto the main channel two directions. Great set up for swimming, fishing, or hanging out watching games on the dock. 2.5 hours from KC, wifi all around the property.

Restful Rustic Comfy Cabin.

Sweet little cabin by a little pond at the edge of the woods. Large sunny windows, real bed, (with room to bed a child or two down on the floor) tea pot, easy chair, composting toilet, AC, WiFi, hiking trails. There's no shower in the Cabin. Our water is from a deep well, tested, certified ... and delicious! There is an above ground pool, trampoline, and a trail down the hill Very child friendly. We maintain a fragrance-free facility, so no air "fresheners".

Four Loves Cottage - Urban Farm

Welcome to Four Loves Cottage, a charming European-style retreat nestled alongside Four Loves Urban Farm in Eldon, MO. Relax in your private, fenced backyard with a fire pit, swing, and hammock, explore our flower gardens, enjoy fresh produce, and meet our friendly chickens. Just one block from downtown, you’ll be close to hiking trails, local shops, and dining. Experience the charm of a European cottage on our urban farm oasis—book your stay today!