Vacation rentals in Olean

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Top-rated vacation rentals in Olean

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Guest favorite
An interior view of the Bunk House showcases two twin bed frames adorned with quilts in various colors. Soft pillows are arranged on each bed, while a large window allows natural light to illuminate the space. Air-conditioning unit is visible on the wall.
Farm stay in Holts Summit
4.92 out of 5 average rating, 274 reviews

The Bunk House

The Bunk House is an 8 by 12 foot shed with 3-4 bunks. There is a twin sized bed across the back, a bunk sized bed on each side and a plank to pull out to accommodate a fourth person in the middle over the walkway. With this adaptation, you have an 8 by 10 foot bed. We provide foam mattresses, sheets, blankets and pillows. There is an air-conditioner and a heater. Bucket toilet behind the bunkhouse. Fire ring available. No pets. The water is from our deep well - tested, certified and delicious!

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, 147 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!

Top guest favorite
The charming stone cottage features a welcoming yellow door, flanked by two bright yellow chairs on a wooden porch. Large windows provide views of the surrounding greenery, enhancing the rustic appeal of the home. A small side table sits adjacent to the chairs.
Cabin in Edwards
4.98 out of 5 average rating, 111 reviews

Cozy retreat! Hot Tub, Wood Stove and Sunsets

Welcome to Cairn Cottage, a classic one-room, stone cottage sitting a stones throw from the Osage Arm of The Lake of the Ozarks (69MM). Relax in nature from the cabin hot tub year around. From May to September (and sometimes later) you can enjoy the Kayaks and SUPs at the lake lot. Please note that the cottage and lake lot are a short drive from each other. A boat slip is available 5/31-9/7 upon request. We always recommend travel insurance but especially encourage it during winter months

Guest favorite
Condo in Lake Ozark
4.95 out of 5 average rating, 133 reviews

Lake views: Couple retreat/Family time/Remote work

Under new cleanership 9/1! Truly a guest favorite at the lake! If you're looking for the BEST VIEW of the main channel, you’ve found it! 1 bedroom, 1.5 bath, top floor condo with a loft and HUGE private balcony on the water where you can nestle into a hammock and immerse yourself in views of summer sunsets and stargaze. Located on the desirable Horseshoe Bend—close to restaurants, bars, golf courses, & more! The complex also has a pool with lake views (mid May-mid Sept.) Boat+PWC slip May-Sept.

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
4.96 out of 5 average rating, 314 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
A screened-in deck features comfortable wicker seating with blue cushions and a hammock, providing a relaxing space to enjoy the panoramic lake view. Light curtains sway gently with the breeze, framing the serene outdoor atmosphere accessible from both living areas.
Condo in Lake Ozark
4.98 out of 5 average rating, 174 reviews

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!"

Top guest favorite
The sunroom features ample natural light from large windows, revealing views of the outdoors. Wicker seating, complemented by red accent pillows, surrounds a glass-top coffee table. White curtains frame the windows, enhancing the airy atmosphere of this inviting space.
Home in Jefferson City
5 out of 5 average rating, 132 reviews

Hillsdale Haven-Charming 2BD,2BA

Unwind at Hillsdale Haven! Newly updated, this sunny home boasts multiple gathering spaces and is fully equipped for that "home away from home" feeling. Relax with your coffee in the sunroom or cozy up in the basement for a movie and games. Located on the west side of town, walking distance to Memorial Park. Easy access to the Capitol, Downtown, the Katy Trail and other attractions. Perfect for families, Katy Trail bikers, legislators, traveling nurses or anyone looking for a getaway.

Top guest favorite
An outdoor seating area features a round, suspended chair with cushions, offering a panoramic view of the Gasconade River valley. Natural sunlight filters through the trees, casting soft shadows across the wooden deck.
Cabin in Dixon
4.99 out of 5 average rating, 130 reviews

Cabin in the Sky

Take it easy at this unique and tranquil getaway overlooking the breathtaking Gasconade river valley. This cabin has many features and was specifically designed to accommodate the view. Large outdoor space with dining table, grill and extra seating. Close proximity to Fort Leonard Wood. Also minutes from public boat ramp and public hunting land. Interior features Wi-Fi-,full kitchen, laundry. Family friendly--kids are welcome. Several family-friendly activities nearby in St. Robert.

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, 128 reviews

Beautiful Grain Bin Cabin, 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.

Superhost
A rustic front porch features wooden paneling illuminated by hanging lights. Two wooden chairs are positioned beside a wreath-adorned door. A broom rests against the wall, while a wooden crate holds antlers, adding character to the welcoming entryway.
Farm stay in California
4.9 out of 5 average rating, 287 reviews

The Shouse

The Shouse is a rustic living quarters built directly under the same roof as our horse stable. Bring your horses along and they can stay here too. The home has recently been fully renovated from an Amish tack shop. It is located in the heart of an Amish community. Spend your evenings relaxing on the front porch and watch the horse and buggies go by. Ask about booking your own buggy ride while you stay to get the most out of your visit!

Top guest favorite
A contemporary living area features a large sectional sofa, an electric fireplace below a wall-mounted TV, and a striking feature wall of natural stone. Sliding glass doors open to a patio with views of the water, allowing natural light to fill the space.
Condo in Osage Beach
4.94 out of 5 average rating, 131 reviews

Lake Life Location with Serenity

Enjoy a peaceful and stylish stay at this unique lakefront condo in Osage Beach! Located just minutes from shopping, entertainment, and recreation venues, this 2-bed, 1-bath vacation rental provides a serene escape from the concrete jungle. Spend your days boating, fishing, jet-skiing, and more on the Lake of the Ozarks, then return home to relax on the deck. Make your next vacation one to remember at this central location!

Top guest favorite
A tranquil view of the cabin from a rocky creek bank, surrounded by lush greenery and trees. The sunset casts a warm glow on the cabin, enhancing its rustic charm. Gentle ripples are seen in the creek, reflecting the evening colors of the sky.
Cabin in Adair Township
4.98 out of 5 average rating, 250 reviews

Cabin on the Creek, 120 Acres

Located at the confluence of two creeks, in real Missouri Ozarks, sits our Cabin. Quant and cozy, this old “hunting cabin” and surrounding land have much to offer. Within the 120 acres of private property, yours to explore, are numerous flowing creeks, ponds, springs, fields, and rolling wooded hills. All ready for your getaway.

Popular amenities for Olean vacation rentals

  1. Airbnb
  2. United States
  3. Missouri
  4. Miller County
  5. Olean