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
A large, wooden deck is showcased, featuring a comfortable seating area with a cushioned sofa. Potted plants are placed strategically, enhancing the serene atmosphere. The sun sets on the horizon, illuminating the landscape, which includes rolling hills and a river in the distance.
Home in Kaiser
5 out of 5 average rating, 42 reviews

Views for Miles, Balconies, Billiards, Arcade, Bar

Perched above the Osage River and Osage National Golf Course, Sunset Bluff delivers stunning views from every room and three private balconies. Enjoy a game room with billiards, shuffleboard, and arcade games, then relax by the unique fire pit. Cook with ease in the fully stocked kitchen or fire up the outdoor grill. Just 13 minutes from Bagnell Dam’s dining, shopping, nightlife, beaches, boating and attractions, this elevated retreat is a perfect Lake of the Ozarks getaway for any family/group.

Top guest favorite
A serene bedroom features a spacious bed with white cotton bedding, complemented by a textured blanket. Two large windows are dressed in patterned curtains, allowing ample light to illuminate the room. A wooden nightstand with books and a small plant adds a touch of decor.
Home in Jefferson City
5 out of 5 average rating, 35 reviews

The Office

This unique place has a style you will love. The Office will be your private space to take care of business while away from home. With a dedicated office space & well appointed living area you will enjoy home away from home comforts. Such as fully stocked kitchen, washer and dryer, two bedrooms with white cotton bedding, and a walk in shower. Whether visiting the capital city for work or pleasure, the location, just west of town, will have you anywhere local within minutes. Close to Binder Lake.

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, 177 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
An outdoor patio area features a large hot tub surrounded by a wooden privacy fence. Nearby, a dining set with four chairs is positioned beside potted plants. The backdrop includes a lush green landscape under a partly cloudy sky.
Home in Jefferson City
4.97 out of 5 average rating, 147 reviews

Modern Farm, Hot Tub, 3 King Bed

Hidden Gem like no other! This beautifully decorated, private home, sits in a quiet residential area and boasts 3 King Bedrooms, 3 Baths, a large Rec area downstairs, outdoor patio and Large Hot Tub with privacy fence. The kitchen is fully stocked for a feast. Located on the South Side, with easy access off Hwy 179, you have easy access to anywhere in the city. Also conveniently located 35 miles from Columbia, and 40 miles from the Lake of the Ozarks. Close to Katy Trail, Wedding Venues

Guest favorite
Chalet in Lake Ozark
4.92 out of 5 average rating, 61 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!

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
4.91 out of 5 average rating, 58 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
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, 164 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
A welcoming porch features a vibrant green door and wooden decking, surrounded by natural greenery. Two comfortable chairs are positioned for relaxation, enhancing the inviting entryway to the house.
Home in Gravois Mills
4.98 out of 5 average rating, 234 reviews

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!

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, 185 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.

Guest favorite
The log cabin is illuminated by warm lights along the porch, casting a welcoming glow against the twilight sky. Surrounding trees frame the cabin, while soft path lights highlight the entryway. The setting evokes a serene atmosphere, ideal for evening relaxation.
Cabin in Bonnots Mill
4.97 out of 5 average rating, 100 reviews

Celestial Log Cabin on the Confluence

Fantastic Eagle Watching! Enchanting 1940's log cabin overlooks the confluence of the Missouri & Osage rivers in charming Bonnots Mill, MO. Close to Columbia, Hermann & Jeff City. Includes master bedroom, open loft, wood-burning hearths, chef's kitchen, clawfoot tub. Double deck overlooking the confluence is a stargazers dream. Secluded, surrounded by nature, find yourself restored after hiking, antiquing, cooking or drinking wine and taking in the beautiful surroundings

Guest favorite
A spacious yurt is set amid greenery, with a tan exterior that blends into the natural surroundings. The entrance features double doors covered by mesh panels. A welcome sign is placed next to a water cooler on a patterned mat, enhancing the outdoor camping ambiance.
Yurt in Eldon
4.85 out of 5 average rating, 48 reviews

Majestic Oaks Unique Getaway in the Ozarks

Come relax & enjoy the sounds of nature and peacefulness, where we make camping a breeze. Bring whatever you want to eat and you’re all set for an enjoyable stay! We as a family have a love for camping so our goal with the yurt 🛖 is to give others the camping experience without all the work & in a unique way🤩 The yurt is located at the one end of our property so you may see/hear us and our kiddos out and about some, playing in the yard & etc..

Top guest favorite
Cabin in Edwards
4.98 out of 5 average rating, 40 reviews

Blue Heron HideawayRC*Eagles*Cliffside Lake views

Welcome to Blue Heron Hideaway, a cozy lakeside retreat designed for quiet, connection, and slowing down. Enjoy peaceful mornings, relaxed afternoons, and evenings soaking in the private wood-fired hot tub overlooking the lake. Located on the quieter side of the lake, this space is best suited for adults seeking a calm, unplugged getaway and is not suitable for children.

Popular amenities for Olean vacation rentals

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