Holiday houses in Olean

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Top-rated holiday rentals in Olean

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Top Guest favourite
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

Views for Miles, 3 Balconies, Game Rm, Arcade, Bar

Perched above the lake with stunning views from every room and balcony, this unforgettable retreat is built for fun and relaxation. Enjoy a game room with billiards, shuffleboard, arcade games, and a stylish bar. Cook in the fully stocked kitchen or grill under the stars. Gather around the one of a kind fire pit, then unwind with sunset views from three private balconies. Just 13 minutes from Bagnell Dam, beaches, bars, and restaurants for the perfect lake escape with comfort and adventure all!!

Top Guest favourite
Condo in Lake Ozark
4.96 out of 5 average rating, 165 reviews

Lakeside escape best views/hammocks/saltwater pool

Summer vacation! Truly a guest favorite at the lake-If you're looking for the BEST VIEW of the main channel, then welcome to Tara Condos! 1 bedroom, 1.5 bath, top floor, condo with a loft and HUGE private balcony on the water where you can nestle into hammocks and immerse yourself in views of the stars and summer sunsets. Located on the desirable Horseshoe Bend—close to the fun: the strip, golf courses, & more! Included: Saltwater pool with lake views (mid May-mid Sept) & Boat+PWC slip May-Sept.

Top Guest favourite
A spacious living area features a light-coloured sofa with decorative cushions, accompanied by a coffee table. Large sliding doors lead to a balcony, offering views of the lake. A dining area with a table for four is visible, with additional seating at the counter.
Condo in Osage Beach
4.96 out of 5 average rating, 116 reviews

Cozy Lakefront Condo, Amazing Lake View! 2bd/2bath

This stunning lakefront condo, located at the 17mm in the heart of Osage Beach, offers both convenience and comfort with its tasteful updates and stunning lake views. You will have seasonal access to 1 heated pool that opens May 1, and 2 lakeview pools that open May 15. You can also enjoy the tennis/pickleball/basketball court open year round. Being conveniently located to wineries, restaurants, activities and much more, makes this an enjoyable and relaxing lake retreat for you and your family.

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, 139 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
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, 341 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 favourite
A serene lake view captures the tranquil water reflecting hues of orange, pink, and blue as the sun sets. The silhouette of a covered dock is visible, blending into the peaceful landscape surrounded by trees and distant hills.
Place to stay in Camdenton
4.93 out of 5 average rating, 101 reviews

Lakefront cozy unit with amazing views.

This cozy one-bedroom charmer, part of a lake front 4-plex built in 1959 will not disappoint and offers a comfortable lake stay. You will have incredible views and steps away from the Picnic area and dock. This is a lower unit-steps and/or our boat ramp are available to get to the unit. It offers a rear parking spot if you are comfortable driving on the boat ramp. We are close to Ha Ha Tonka State Park, Kinderhook and Lake Valley Golf courses, Ball Park Nationals, and the Amphitheater.

Top Guest favourite
Condo in Lake Ozark
4.99 out of 5 average rating, 342 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 favourite
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, 220 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 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, 169 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
A cozy cabin is nestled beside a tranquil pond, surrounded by lush greenery. Canoes rest gently on the bank, reflecting the trees and cabin in the calm water. The outdoor space features a porch with seating, inviting a peaceful retreat in nature.
Cabin in Holts Summit
4.94 out of 5 average rating, 510 reviews

Restful Rustic Comfy Cabin.

Sweet little cabin by a little pond at the edge of the woods. Large sunny windows, real bed, (with room to bed a child or two down on the floor) tea pot, easy chair, composting toilet, AC, WiFi, hiking trails. There's no shower in the Cabin. Our water is from a deep well, tested, certified ... and delicious! There is an above ground pool, trampoline, and a trail down the hill Very child friendly. We maintain a fragrance-free facility, so no air "fresheners".

Top Guest favourite
Cabin in Roach
4.96 out of 5 average rating, 149 reviews

Ridge Top Meadows Guest Cabin

Relax in this beautiful private setting! This single-bedroom log cabin is located just minutes from Lake of the Ozarks, Ha-Ha Tonka State Park, Niangua River, and Ball Parks National. Amenities include full kitchen, bathroom with shower, queen bed, loft with twin mattress, dining table, Keurig coffee, TV (no cable) and DVD player, fire pit, picnic table, tent camping area, and hiking trail. No Saturday check in.

Top Guest favourite
A covered porch with string lights creates a cozy gathering spot. The seating arrangement, designed for relaxation, overlooks a natural landscape. The cabin's exterior features wooden elements and is surrounded by trees, enhancing a sense of privacy and connection to nature.
Earthen home in Columbia
4.97 out of 5 average rating, 148 reviews

Creekside Cabin Getaway

Cabin on almost 70 acres with Bass Creek running through it. Direct access to highway 63 and minutes south of Columbia. Perfect setting for a family gathering or a relaxing weekend getaway. Established trails for hiking and biking with rustic benches to stop and enjoy nature. We hope you enjoy Hills and Valleys Retreat as much as we do. (Additional cabin available to rent.)

Popular amenities for Olean holiday rentals

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