Vacation rentals in Olean

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Top-rated vacation rentals in Olean

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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, 168 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!

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
5 out of 5 average rating, 11 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 3 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.

Top guest favorite
The exterior of the log home is showcased, featuring large floor-to-ceiling windows on the upper level. A wooden deck extends from the front, surrounded by greenery. Two lanterns are mounted on the railing, enhancing the natural setting.
Cabin in Meta
4.84 out of 5 average rating, 148 reviews

Log cabin retreat on 50 acre farm

Our log home is nestled in the middle of a 50 acre farm in the Ozark foothills, where you can hike, watch wildlife and enjoy complete solitude. You’ll love our place because of the view of foothills, forests, prairie, and farm. Amazing star gazing, a brook spring out the back door. Designed to blend in with nature - the 1900 square foot lodge has a floor to ceiling window wall. We're close to canoeing/rivers, Painted Rock Conservation Area. Jefferson City is a 20 mi. drive. Lake Ozarks - 45 mi.

Guest favorite
A spacious wooden porch is featured, with several Adirondack chairs arranged comfortably. Natural wood elements and autumn leaves create a calm setting. Full-length windows offer glimpses of the surroundings, while the latticework adds texture and visual interest to the porch design.
Home in Bonnots Mill
4.94 out of 5 average rating, 337 reviews

Secluded "Heaven": soaker tub, sauna, sunset view

"Heaven" ( 1,512 sq ft, 7 ac) sits on a bluff overlooking the Osage river. An open home with huge full length windows and a sun room provides abundant natural lighting. Two porches offer views over the river and to the woods. A soaker tub and sauna are situated in the cabin with a view to the sunset. The cabin is at the end of a secluded forest road. A locked garage is available for parking small cars. Drive: 15-20 min to Linn for supplies / 30 min to Jeff City / 5 min to public river access.

Top guest favorite
Cabin in Edwards
4.99 out of 5 average rating, 138 reviews

Hot tub, golf cart, kayaks/SUP with lake access!

✨Hot Tub+Golf Cart+Kayaks |Quiet Lake Escape Cairn Cottage is a cozy, vintage, one room stone cottage tucked into nature above the Osage Arm (69MM). Come slow down and enjoy the quiet side of the lake. Hot tub year-round, golf cart to the dock, and kayaks in season. A complimentary breakfast casserole, plus coffee and snacks, make mornings simple and relaxed. Not coming in summer? Check out our amenities slide that shares which amenities are available when. Reconnection is a reservation away!

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.
Farm stay in Eldon
4.9 out of 5 average rating, 52 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. Enjoy the serenity of your private patio, explore our vibrant flower gardens, enjoy fresh produce, and meet our friendly chickens. Conveniently located one block away from downtown Eldon, MO, you’ll be close to scenic hiking trails, local shops, and dining options. Experience the tranquility and charm of a European cottage on our urban farm oasis – book your stay today!

Top guest favorite
The modern three-story building features multiple balconies adorned with warm lighting. Steps lead to the entrance, and a serene outdoor area with gravel surrounds the structure. Nearby, additional buildings and a road are visible among the lush greenery.
Condo in Lake Ozark
4.99 out of 5 average rating, 336 reviews

Lake of the Ozarks! Vacation Condo on the Strip-B

Welcome to Paradise City Unit B! 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!

Top guest favorite
A spacious balcony features a comfortable seating area with cushioned sofas arranged around a coffee table. Lush greenery and rolling hills are visible in the background, creating a serene backdrop for relaxation. The warm glow of sunset enhances the tranquil atmosphere.
Home in Kaiser
5 out of 5 average rating, 38 reviews

Expansive Views, Sleeps 9, Amazing Game Room,

Perched above the Osage River and Osage National Golf Course, this hilltop retreat offers stunning sunset views from three private balconies. Inside, enjoy a lively game room with billiards, shuffleboard, and arcade classics, plus a fully equipped kitchen ideal for group meals and late night laughs. Just 13 minutes from Bagnell Dam’s dining, nightlife, beaches, and family attractions, this scenic escape blends comfort, fun, and unforgettable views for a stay you will never forget.

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, 164 reviews

The Highland GrainBin, Highland Cows, Firepit

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.

Top guest favorite
Two blue mugs are placed on a glass-topped table overlooking the serene lake. The calm water reflects the surrounding tree-covered hills, creating a peaceful setting. Soft morning light illuminates the scene, enhancing the tranquil atmosphere of this lakeside retreat.
Home in Edwards
4.97 out of 5 average rating, 278 reviews

Rippling Point Lakefront House

Secluded at the end of a private drive on the quiet end of the Lake of the Ozarks, our lake home offers recreation, relaxation, and fishing opportunities. The house is on the water at the 67MM of the lake and features 300 feet of private shoreline. A deck that overhangs the water is just a few steps from a patio equipped with a propane/charcoal grill and outdoor cooking area. Two kayaks are included to explore the shoreline and its wildlife. An inviting hot tub beckons.

Guest favorite
A charming cabin exterior is presented, featuring a stone facade and a pitched roof. A balcony is visible above the entrance, accompanied by a red chair set on the porch. Lush green lawn surrounds the cabin, with trees providing shade in the background.
Cabin in Osage Beach
4.97 out of 5 average rating, 188 reviews

Cabin No. 4 @ The Old Swiss Village - Lake Views!

Rustic charm + Modern amenities. Our 1930's Cabin rests atop one of the most sought after view corridors at the lake. Over 100 feet above the water offering views of local Firework shows, gorgeous sunsets and a spectacular vantage point when there is activity on the lake. Nestled away in the wilderness, peaceful days and nights are many. Located in the heart of Osage Beach with nearby lake access at the state park, steak house adjacent to property and a wine bar.

Top guest favorite
Home in Rocky Mount
5 out of 5 average rating, 10 reviews

Best views in Rocky Mount

Spring is approaching, grab a few nights and watch spring develop with extraordinary views of the lake. Enjoy some peace and quiet while you enjoy the comforts of home. Enjoy plenty of lake views, only 15 minutes to famous bagnell dam strip. 2 bedrooms, 2 baths, 85” tv for relaxing in the evening or watching the big game. A large 2 story deck for optimal viewing and relaxing. Everything you’d need kitchen or DoorDash aplenty.

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  4. Miller County
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