Vacation rentals in Olean

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Top-rated vacation rentals in Olean

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

The exterior of a historic cottage is visible, featuring a blend of stone and siding with green shutters. A welcoming porch includes a seating area, while the surrounding landscape is adorned with greenery. The structure is situated along a quiet street.

Cottage in California

4.95 out of 5 average rating, 187 reviews

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!

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Guest favorite

A wooden dock extends into a calm lake, reflecting the evening sky's soft blues and subtle clouds. The surrounding hills are visible in the background, providing a serene atmosphere. A covered boat slip is positioned at the end of the dock, enhancing the lakeside experience.

Home in Gravois Mills

4.9 out of 5 average rating, 105 reviews

Large Lake House by Coconuts

The Lake House is ideal for a few individuals or a large group. Get away on the quiet side of the lake with 170' of shore front, beach, fire pit, picnic area, and dock. 1,000' (5 min walk) from the popular Coconuts! 6 bedrooms with 9 beds, 3 couch/futon and 3 baths in this 2,500 sqft home is waiting for you! Large kitchen and living room area. Bottom porch is screened and the upper porch is ready for the kids! Less than 20 minutes to Ozark International Raceway. Please list guest count accurate

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Guest favorite

Home in Eldon

4.85 out of 5 average rating, 27 reviews

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

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Top guest favorite

A cozy living room space is highlighted by exposed wooden beams on the ceiling. Seating includes a sofa and two light blue armchairs, arranged around a central coffee table. A television is mounted on the wall, and natural light enters through the windows, creating a welcoming environment.

Home in Rocky Mount

4.97 out of 5 average rating, 30 reviews

The Blue Heron Cottage- NO WAKE COVE

Relax with family at this peaceful waterfront cottage on Lake of the Ozarks. Our NO WAKE cove is the perfect spot to swim, kayak, fish, or just hang out in the outdoor living space on the dock. A 9x26 boat slip is available on the dock and 2 kayaks during your stay. Located in Lick Branch Cove on the 5mm, just a short boat ride from Shady Gators, Tap and Grill, Boat House , Docknockers and many others . 18 minutes away from the Bagnell Dam strip and 25 minutes away from Osage Beach by land.

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Guest favorite

Chalet in Lake Ozark

4.92 out of 5 average rating, 72 reviews

Lakegaze Chalet - Amazing View/Incredible Fun!

Whether it's a romantic get-away, family vacation, girls or guys retreat, Lakegaze Chalet is the perfect A-Frame with an Incredible Lakeview (second tier), Huge Deck, Firepit, Hammocks, 3 Electric Fireplaces, 3 large TV's, Reading Nook, Mini Disc Golf, Putt Putt Golf, Ping Pong, Cornhole & more! Perfect memories at the lake! Just a few minutes from the strip, boat ramp just down the road, options nearby for docking, space for 5 vehicles, boat trailer parking. Peaceful but fun = perfect vacay!

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Guest favorite

A single-story house nestled among trees features a combination of stone and wood siding. A grassy yard surrounds the home, with a gravel pathway leading to the entrance. Large trees provide shade, enhancing the natural setting.

Home in Versailles

4.94 out of 5 average rating, 32 reviews

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

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Top guest favorite

The image captures a sleek, modern building situated on a hillside, with large windows reflecting the evening light. The surrounding area includes greenery and a glimpse of the water, with a road and several structures visible in the distance under a colorful sky.

Condo in Lake Ozark

4.99 out of 5 average rating, 348 reviews

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! .

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Top guest favorite

Apartment in Lake Ozark

4.96 out of 5 average rating, 23 reviews

Beautiful Lake Ozark Condo with NO cleaning fees

Stunning Lake View Retreat – Your Mile Marker 3 Oasis Escape to the heart of the Lake of the Ozarks. Whether you are looking for a weekend getaway, a family vacation, or a relaxing home base for your lake adventures, this condo offers the perfect blend of comfort, convenience, and breathtaking views. Covered boat slip with electricity available for extra fee. Boat ramp on site. Kayaks and floats available for lazy lake days. Additional unit adjacent to this one. airbnb.com/h/jccondo

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Top guest favorite

Home in Rocky Mount

5.0 out of 5 average rating, 37 reviews

Heated Pool! Outdoor Kitchen! Private Dock w Pier!

Take it easy at this unique and historic old ski school from the 50s that is now a beautiful lake house on the 5mm. Relax or fish on the grandfathered in pier or take a swim in the heated pool with tanning ledge. Hang out around the firepit while you take in the 240 feet of flat shoreline. The house is packed with lots of games for both indoor and outdoor. With a beautiful standalone rustic cabin, this is a hidden gem at the lake. Paradise Pier is a short 3-minute walk to Jolly Rodgers

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Top guest favorite

The exterior of the Grain Bin Cabin is showcased beside a tranquil pond, reflecting the cabin's metallic structure. Adirondack chairs surround a firepit on the grass, with picnic tables positioned nearby, creating an inviting outdoor space.

Cabin in Versailles

4.99 out of 5 average rating, 198 reviews

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.

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Top guest favorite

Home in Kaiser

4.98 out of 5 average rating, 48 reviews

Views for Miles, Balconies, Billiards, Arcade, Bar

Escape to Sunset Bluff, where panoramic views of the Osage River and Osage National Golf Course shine from every room and three private balconies. Enjoy billiards, shuffleboard, and arcade games, gather around the custom fire pit, or cook in the fully stocked kitchen and outdoor grill. Just 13 minutes from Bagnell Dam, Backwater Jacks, beaches, boating, shopping, dining, nightlife, and family attractions. Perfect for families, friends, reunions, and unforgettable getaways!

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Top guest favorite

A cozy kitchen area features light-colored cabinetry adorned with decorative plates and coffee equipment. A round dining table is set with dishes and a vase of sunflowers. The space is complemented by rustic brick flooring and climbing greenery along the walls.

Cottage in Eldon

4.93 out of 5 average rating, 67 reviews

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!

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