Holiday rentals in Olean

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Top-rated holiday rentals in Olean

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

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Top guest favourite
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 favourite
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 favourite
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!

Guest favourite
A panoramic view of a resort pool area is displayed, surrounded by lush greenery and a scenic golf course. Comfortable lounge chairs and shaded umbrellas are arranged around the pool, with walking paths and water features enhancing the serene atmosphere.
Apartment in Lake Ozark
4.9 out of 5 average rating, 70 reviews

Lake of the Ozarks Golf Retreat with boat options.

Welcome to Osage National! This condo is bottom floor, cozy, quiet and convenient to the best golf course at Lake of the Ozarks. Enjoy the peaceful resort setting. Amenities include clubhouse, dining, pool and more! Condo features 2 bedrooms, 2 full baths, comfortably sleeps 5. Includes fully stocked kitchen, washer/dryer, HDTV, Free and Fast WiFi, private patio area. Location is just minutes away to the Lake, boating, fishing, shopping, attractions, many restaurants & more. Book now !

Top guest favourite
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 favourite
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 favourite
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
4.93 out of 5 average rating, 29 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

Guest favourite
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 favourite
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.

Top guest favourite
The exterior of a single-story home is shown, featuring a brick façade and a gabled roof. A flag is displayed prominently at the entrance. A well-maintained lawn surrounds the house, with several trees visible in the background against a cloudy sky.
Home in Jefferson City
4.97 out of 5 average rating, 62 reviews

RM totally remodeled specialty

Forget your worries in this spacious and serene space. This totally remodeled house has everything to relax and the feel of home away from home. This 2 bed, 2 bath and an office home has been totally updated with new floors, carpet, trim, crown moulding, appliances and much more. THIS IS A SMOKE FREE/PET FREE HOME. MUST BE 24 TO RENT THIS HOME. VERY FAMILY ORIENTED. In a great neighborhood. House and guest protected by outside cameras . Great location!

Top guest favourite
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.

Guest favourite
Flat in Rocky Mount
4.93 out of 5 average rating, 29 reviews

2 Bed Lakeview unit w/ HotTub & Lake view

Indulge in a luxurious private upstairs unit featuring a DreamCloud king suite, a beautifully designed queen bedroom, and premium, ultra-soft bedding throughout. Enjoy your private deck, carport parking, and access to upscale outdoor amenities including a hot tub, BBQ grill, and Ninja Fireside 360 fire pit. Styled by a local designer for a boutique experience.

Popular amenities for Olean holiday rentals

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