Holiday Rentals in Olean

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Holiday Rentals in Olean

Business or Pleasure - a perfect and cozy get-away!

Jefferson City
9.6 out of 10, Exceptional, (28)
"Perfect place to stay for my trip"
United States
Joshua B.
The price is €145
includes taxes & fees
30 Nov - 1 Dec
Business or Pleasure - a perfect and cozy get-away!

Balcony w/ Marina Views: Lake Ozark Hideaway!

3.0 star property
Sunrise Beach
10.0 out of 10, Exceptional, (1)
"Great views and such a cute condo. Loved this place"
United States
Angela
The price is €258
includes taxes & fees
28 Nov - 29 Nov
Balcony w/ Marina Views: Lake Ozark Hideaway!

Lakefront Condo, 2 Bed, 2 Bath-Sleeps 6, Pool, Hot Tub, Tennis Courts, Swim Dock, WIFI

Lake Ozark
10.0 out of 10, Exceptional, (11)
"Clean, had great coffee, super cute decor and they even brought propane super fast because it was empty. Highly recommend and we will be coming back."
United States
Shelby
The price is €153
includes taxes & fees
1 Dec - 2 Dec
Lakefront Condo, 2 Bed, 2 Bath-Sleeps 6, Pool, Hot Tub, Tennis Courts, Swim Dock, WIFI

“Clabe” one of the 5 Tiny Cabins on the Osage River

Tuscumbia
10.0 out of 10, Exceptional, (2)
"It was a great quiet place to get away for a weekend."
United States
Kyle B.
The price is €156
includes taxes & fees
26 Nov - 27 Nov
“Clabe” one of the 5 Tiny Cabins on the Osage River

The Carriage House at Parker's Place

Jefferson City
10.0 out of 10, Exceptional, (45)
"Perfect location and very comfortable place. "
United States
Holly B.
The price is €264
includes taxes & fees
3 Dec - 4 Dec
The Carriage House at Parker's Place

The Big House, Historic 4-Bedroom Home With Custom Art And Dedicated Workspace

2.0 star property
Jefferson City
10.0 out of 10, Exceptional, (28)
"It was very nice"
United States
Chase O.
The price is €263
includes taxes & fees
1 Dec - 2 Dec
The Big House, Historic 4-Bedroom Home With Custom Art And Dedicated Workspace

Emerald Escape – Luxury Waterfront Condo w/Pool!

Lake Ozark
9.6 out of 10, Exceptional, (10)
"Very nice and clean place to stay."
United States
Ryan K.
The price is €251
includes taxes & fees
26 Nov - 27 Nov
Emerald Escape – Luxury Waterfront Condo w/Pool!

Sunset Spectacular – Waterfront & Indoor Pool!

Village of Four Seasons
10.0 out of 10, Exceptional, (5)
"The unit was spacious. The area was great. The pool was nice as well and stayed open until midnight! "
United States
Josh W.
Sunset Spectacular – Waterfront & Indoor Pool!

Stylish Lakefront, King Bed Suite, Sunset View, Pool, Boat Slip, PrivateTopFloor

Osage Beach
10.0 out of 10, Exceptional, (86)
"Great views! Loved our stay!"
United States
Douglas K.
Stylish Lakefront, King Bed Suite, Sunset View, Pool, Boat Slip, PrivateTopFloor

The Sunrise Suite – Waterfront Screened Balcony w/Pool!

Lake Ozark
9.8 out of 10, Exceptional, (8)
"This condo was absolutely amazing it had everything you could need and more ! It was the perfect getaway for my children and I ! "
United States
Amanda M.
The price is €241
includes taxes & fees
26 Nov - 27 Nov
The Sunrise Suite – Waterfront Screened Balcony w/Pool!

Emerald Oasis - Waterfront, Pools, & Smoker!

Lake Ozark
10.0 out of 10, Exceptional, (6)
"Lovely property, Unit, & Location. Would stay again"
United States
Steven W.
The price is €280
includes taxes & fees
30 Nov - 1 Dec
Emerald Oasis - Waterfront, Pools, & Smoker!

Lake Life Lookout – Pools, Hot Tub, & More!

Lake Ozark
9.8 out of 10, Exceptional, (11)
"Well-kept and decorated"
United States
Tim S.
The price is €247
includes taxes & fees
26 Nov - 27 Nov
Lake Life Lookout – Pools, Hot Tub, & More!

Completely Remodeled@1MM - Early Check In - Late Check Out - Close to the strip

2.5 star property
Lake Ozark
10.0 out of 10, Exceptional, (3)
"If you're looking for a great place to call home on your trip - this is the place to do it! Rachel's place was better than described and we were even greeted with snacks and champagne for Mimosas. The place was spotless and very well stocked with about anything you would need for your stay. As for your host "Rachel" she went above and beyond, and you'll have a hard time finding a better one. Communication was absolutely seamless. "
United States
Joseph P.
Completely Remodeled@1MM - Early Check In - Late Check Out - Close to the strip

Turtle Cove – Lakefront & Indoor Pool!

Village of Four Seasons
9.6 out of 10, Exceptional, (7)
"We had a wonderful relaxing stay. The condo was perfect."
United States
Kasie W.
The price is €248
includes taxes & fees
26 Nov - 27 Nov
Turtle Cove – Lakefront & Indoor Pool!

Posh Penthouse-Top Floor, Waterfront, Pools, & Pickleball!

Village of Four Seasons
10.0 out of 10, Exceptional, (7)
"This place was perfect for our needs (Family of 4 with plenty of room when using sofa bed). Very clean!"
United States
Vince G.
Posh Penthouse-Top Floor, Waterfront, Pools, & Pickleball!

4 Bedroom Comfortable Cottage

3.0 star property
Versailles
9.0 out of 10, Wonderful, (2)
"Very clean, nice and comfortable place."
United States
Jenny M.
The price is €459
includes taxes & fees
7 Dec - 8 Dec
4 Bedroom Comfortable Cottage

Our Cove Retreat - Perfect for Wave-Free Swimming, Tanning & Prime Location Fun!

Lake Ozark
9.8 out of 10, Exceptional, (23)
"Great stay. Great location close by everything you could need or want. "
United States
John
Our Cove Retreat - Perfect for Wave-Free Swimming, Tanning & Prime Location Fun!

Charming cabin with WiFi and AC in delightful Eldon

Eldon
9.0 out of 10, Wonderful, (7)
"Wonderful cabin. Absolutely recommend!!"
United States
Vivian
The price is €143
includes taxes & fees
29 Nov - 30 Nov
Charming cabin with WiFi and AC in delightful Eldon

Lakeside Paradise - Waterfront, Pools, & Pickleball!

Lake Ozark
9.6 out of 10, Exceptional, (5)
"This condo was amazing!!! Had everything we needed, would highly recommend!!"
United States
Kathryn H.
The price is €248
includes taxes & fees
26 Nov - 27 Nov
Lakeside Paradise - Waterfront, Pools, & Pickleball!

Private Four Season Condo (2BED/2BATH/2 Balconies-Pool, Hottub, Golf, Spa, Marina-6PP)

Lake Ozark
8.4 out of 10, Very good, (7)
"Needed a quick one night stay and was perfect for 2 couples. Everything was nice and have all essentials for the perfect stay."
United States
Blake J.
The price is €173
includes taxes & fees
8 Dec - 9 Dec
Private Four Season Condo (2BED/2BATH/2 Balconies-Pool, Hottub, Golf, Spa, Marina-6PP)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Olean Hotel Reviews

Find out more about Olean

Everything you need to know about Olean holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Olean holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Olean holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Olean holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Olean. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Olean holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Olean holiday rentals we have selected for you start as low as €688 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Olean rentals

At Expedia, we put the best Olean holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Olean rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Olean holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Olean. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Olean?

Yes, there are holiday rentals close to the most popular sights in Olean, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Olean has to offer?

Kayaks~ Hot Tub~Steps from the Lake~Massive House, Game Room-Centrally Located: This holiday home rental outside of Olean is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

What’s there to see and do in Olean?

While exploring the area, visit family-friendly sights like Willmore Lodge, or get outside and enjoy nature at Possum Hollow Cove. In the wider area, you’ll find Osage National Golf Club and Lake of the Ozarks and Bagnell Dam Viewpoint.

What’s a holiday rental in Olean like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Olean. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for a family trip or a small group gathering.