Vacation rentals in Olean

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Top-rated vacation rentals in Olean

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Top guest favorite

Cottage in Village of Four Seasons

4.99 out of 5 average rating, 85 reviews

Lake Front Cottage - Four Seasons - Mile Marker 13

Lake Front cottage w/ amazing views from the custom deck. Your Tree Top view looks down on 1 of 3 outdoor pools. Public boat slips are steps away for fishing, swimming, or docking your boat. Beautiful 2 level home, w/ main level master king bedroom. The cottage has a main level full kitchen, dining & living room, and 2 full bathrooms. The living room converts to a bedroom, w/ a queen sofa sleeper. The lower level has a bedroom w/ a Queen bed, bunk bed, 3rd full bathroom & Queen Sleeper Sofa.

Superhost

A stone fire pit is surrounded by grass, nestled near the water's edge. The calm lake reflects the greenery of the wooded area that lines the shore, providing a peaceful backdrop. Nearby, a boat dock is partially visible, enhancing the serene outdoor setting.

Cottage in Edwards

4.85 out of 5 average rating, 20 reviews

Horse Shoe Hideaway

Take it easy at this unique and tranquil getaway. Approximately 1/2 hour from Warsaw, in a quiet cove perfect for relaxing. This cozy 2 bed, 1 bath is nestled back in the trees and rocks making it feel private and secluded with WIFI, tv and free parking. Guest can enjoy nature, fishing, kayaking and swimming. Grill on the BBQ or cook your favorite meals in the fully equipped kitchen. Guest can enjoy indoor/outdoor dining, play yard games and sit around the fire pit for an end to a cozy evening.

Top guest favorite

Apartment in Osage Beach

5 out of 5 average rating, 23 reviews

Views for Days Condo

Welcome to your perfect getaway! This newly remodeled gem offers amazing unobstructed views of the lake. Enjoy year-round relaxation with an indoor pool, hot tub, and sauna, ensuring comfort and leisure regardless of the season. During the warmer months, take advantage of the outdoor pool. The property also features an indoor tennis court, pickleball courts, boat launch, and boat trailer parking. Conveniently located within minutes of popular dining spots such as Redheads and Jeffrey’s.

Top guest favorite

A spacious outdoor deck features wooden flooring, surrounded by wooden railings. A ceiling fan is mounted above, providing airflow. A wall-mounted TV is visible alongside large windows, showcasing views of the surrounding greenery. Natural light enhances the open and airy feel of the space.

Condo in Lake Ozark

4.99 out of 5 average rating, 254 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

An aerial view captures the condo complex along the shoreline, with multiple structures arranged in a row. The scenic lake is visible, framed by lush greenery on the opposite bank. Several boat docks are seen, providing a view of water activities in the area.

Condo in Lake Ozark

5 out of 5 average rating, 12 reviews

Lakeside Getaway: Book Now!

Welcome to Lake of the Ozarks Paradise! Experience pure bliss in our charming 2 bed, 2 bath condo with breathtaking lake views. Nestled in a prime location, you'll have easy access to water activities and nearby attractions. Unwind on the private balcony, savoring the serene sunsets over the shimmering waters. Enjoy modern amenities and a fully equipped kitchen. Whether it's fishing, boating, or simply relishing the tranquility, this condo offers an unforgettable retreat. Book now!

Top guest favorite

A screened-in balcony offers serene views of the lake, with sunlight reflecting on the water. A round table surrounded by four comfortable chairs and a small plant centerpiece enhances the inviting outdoor space, ideal for relaxation or dining.

Condo in Rocky Mount

5 out of 5 average rating, 14 reviews

Pool • Balcony • Island • King • 505Mbps • Smart TVs

⭐️Escape to an exclusive oasis ⭐️ at this stunning 3-bed, 2-bath condo on Lake of the Ozarks. Nestled on the lake's only habitable island, you will be surrounded by the lake’s breathtaking beauty. With 360-degree views and a bridge for easy access, this condo is the perfect setting for a memorable getaway with family or friends. ⭐️-“Truly a luxury getaway. Wonderful place and location” ⭐️-“Clean, updated, spacious, comfortable beds & screened in balcony which was a major bonus”

Guest favorite

Condo in Osage Beach

4.95 out of 5 average rating, 22 reviews

Perfect Main Channel Views 3 Bd/2 bath/4 total bds

Your family will be close to everything when you stay at this centrally-located condo Offering 19 MM MAIN channel views, with a screened in patio and private dock. This great location offers a Boat rental, PWC and one of the best bars on the lake as neighbors Dog Days bar and grille. Walk just a few yards and you are there. This unit is newly remodeled making it easy for you to relax and enjoy the lake life. For the Fishermen we have had good luck catching Crappie off the dock.

Guest favorite

Home in Sunrise Beach

4.96 out of 5 average rating, 27 reviews

Sunrise, Wildlife, Kayak & Paddle Boarding Awaits!

Escape to the ultimate vacation rental: a beautifully redesigned home with vibrant colors, two family sleeping areas, private hot tub and an amazing king master suite. Located in the sought-after Buck Creek neighborhood, this property features two decks for stunning lake views. Enjoy ample parking and proximity to lakefront activities, dining, family-friendly venues, and vibrant nightlife. Experience impeccable design, comfort, and a prime location for unforgettable memories.

Guest favorite

A screened-in balcony features a gas grill and a round glass dining table with four chairs. Two ceiling fans are mounted above, providing a breeze. The view showcases a calm lake with boat docks and greenery in the background.

Condo in Osage Beach

4.93 out of 5 average rating, 86 reviews

Specials lakefront, Updated 3BR/2BA condo

Spring/Summer Specials... BEST LOCATION ON LAKE* 1st Floor! 3BR 2BA Condo *50" Fireplace w/heat * Veteran Owned* Big Screened in Balcony w/sofa seating 2-ceiling fans BBQ grill/smoker, right on waterfront * 3 private pools w/ lake views. 4 Smart TVs. Close to boat/ jet ski rentals. Golf, shopping, restaurants, Gokart/MiniGolf. Best fishing!! PWC/Boat slips maybe available. Have fun & enjoy this beautiful lake side retreat. Free 5G WiFi. Keyless Door. Great 4 Families!

Guest favorite

A serene lakeside view is captured from a private patio, showcasing calm waters reflecting the surrounding greenery. Comfortable lounge chairs are positioned for relaxation, with a tree providing shade. The gentle landscape leads to distant homes and a bridge, enhancing the tranquil atmosphere.

Condo in Osage Beach

4.89 out of 5 average rating, 283 reviews

WOW! Location! On the water! Spectacular!

Welcome to your dream vacation! This beautifully appointed condo in the heart of Osage Beach is ready for you. Enjoy easy access to the Lake of the Ozarks and all the best attractions. You'll love boating, fishing, and the stunning lake views. Plus, golf courses, wineries, and fantastic dining are just moments away. With three pools, sports courts, and a spacious deck, you'll have everything you need for an unforgettable stay for up to 8 guests!

Superhost

A spacious hot tub sits on a wooden deck surrounded by trees with autumn leaves. Sunlight reflects off the water, creating a serene setting, while a comfortable chair is positioned to enjoy the view of the lake.

Home in Lake Ozark

5 out of 5 average rating, 3 reviews

Waterfront Paradise/HotTub/Boat&JetSki Options

Enjoy one of the best views of the lake! Minutes from everything the lake has to offer, this home is located down Horseshoe Bend close to the Lodge of the Four Seasons on the south shore at the 9.5 mile marker. The home boasts a huge deck with a hot tub and a private dock with a swim platform! And the icing on the cake is that you can rent a boat and jet skis without leaving the home! Book an escape to this waterfront paradise today!

Guest favorite

An outdoor covered porch features a large dark wood dining table surrounded by wicker chairs, ideal for meals with a view. A lantern sits at the center of the table. Nearby, a grill and additional seating can be seen, with lake views through the railing.

Home in Osage Beach

4.95 out of 5 average rating, 147 reviews

Margaritaville Resort area. Grill. Lake view

This stylish 3-bedroom, 2-bath home in the Margaritaville resort area offers the perfect blend of convenience, privacy, and luxury amenities for an unforgettable vacation experience. Enjoy stunning lake views from the comfort of your own private covered porch, creating a serene and relaxing atmosphere. With 3 bedrooms and 2 baths, there's plenty of space for families or groups of friends to relax and unwind.