Olean Vacation Rentals

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Jan 23 - Jan 25
In two months
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In three months
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In four months
May 1 - May 3

Our top choices for Olean vacation rentals

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

Apartment in Jefferson City

Business or Pleasure - a perfect and cozy get-away!
9.6 out of 10, Exceptional, (29)
"Perfect place to stay for my trip"
United States
Joshua B.
$157 nightly
The price is $163
Jan 10 - Jan 11
Total with taxes and fees
Business or Pleasure - a perfect and cozy get-away!
Private kitchen
Historic 4-bedroom pet friendly rental close to downtown.

Vacation Home in Jefferson City

Historic 4-bedroom pet friendly rental close to downtown.
2.0 star property
$289 nightly
The price is $289
Jan 9 - Jan 10
Total with taxes and fees
Historic 4-bedroom pet friendly rental close to downtown.
Fridge, microwave, oven, stovetop
The Carriage House at Parker's Place

Cottage in Jefferson City

The Carriage House at Parker's Place
10.0 out of 10, Exceptional, (46)
"Perfect location and very comfortable place. "
United States
Holly B.
$273 nightly
The price is $273
Jan 11 - Jan 12
Total with taxes and fees
The Carriage House at Parker's Place
Outdoor dining
“Clabe” one of the 5 Tiny Cabins on the Osage River

Cabin in Tuscumbia

“Clabe” one of the 5 Tiny Cabins on the Osage River
10.0 out of 10, Exceptional, (2)
"It was a great quiet place to get away for a weekend."
United States
Kyle B.
$165 nightly
The price is $176
Jan 9 - Jan 10
Total with taxes and fees
“Clabe” one of the 5 Tiny Cabins on the Osage River
Living area
A Home Away From Home

Apartment in Jefferson City

A Home Away From Home
2.0 star property
7.6 out of 10, Good, (4)
"Very spacious, clean, and easily accessible"
United States
Briana
$171 nightly
The price is $176
Jan 30 - Jan 31
Total with taxes and fees
A Home Away From Home
Property grounds
Cozy 1-bedroom condo in charming Village of Four Seasons with WiFi, fitness room

Condo in Village of Four Seasons

Cozy 1-bedroom condo in charming Village of Four Seasons with WiFi, fitness room
10.0 out of 10, Exceptional, (8)
"Condo was just as expected and in a great location!"
United States
Ashley R.
$163 nightly
The price is $166
Jan 9 - Jan 10
Total with taxes and fees
Cozy 1-bedroom condo in charming Village of Four Seasons with WiFi, fitness room
Property grounds
Cozy 1-bedroom condo with WiFi, AC in peaceful Lake Ozark. Prime location on 4MM

Condo in Lake Ozark

Cozy 1-bedroom condo with WiFi, AC in peaceful Lake Ozark. Prime location on 4MM
10.0 out of 10, Exceptional, (12)
"Very happy with our stay, and the great communication with our host. "
United States
Greg K.
$105 nightly
The price is $111
Jan 9 - Jan 10
Total with taxes and fees
Cozy 1-bedroom condo with WiFi, AC in peaceful Lake Ozark. Prime location on 4MM
Interior
The Big House, Historic 4-Bedroom Home With Custom Art And Dedicated Workspace

Vacation Home in Jefferson City

The Big House, Historic 4-Bedroom Home With Custom Art And Dedicated Workspace
2.0 star property
10.0 out of 10, Exceptional, (30)
"Very clean and well appointed. Nice location."
United States
Thomas C.
$284 nightly
The price is $297
Jan 9 - Jan 10
Total with taxes and fees
The Big House, Historic 4-Bedroom Home With Custom Art And Dedicated Workspace
Smart TV, fireplace
Charming cabin with WiFi and AC in delightful Eldon

Cabin in Eldon

Charming cabin with WiFi and AC in delightful Eldon
9.2 out of 10, Wonderful, (9)
"Wonderful cabin. Absolutely recommend!!"
United States
Vivian
$150 nightly
The price is $161
Jan 15 - Jan 16
Total with taxes and fees
Charming cabin with WiFi and AC in delightful Eldon
Indoor pool
Turtle Cove – Lakefront & Indoor Pool!

Condo in Village of Four Seasons

Turtle Cove – Lakefront & Indoor Pool!
9.6 out of 10, Exceptional, (7)
"We had a wonderful relaxing stay. The condo was perfect."
United States
Kasie W.
$272 nightly
The price is $278
Jan 11 - Jan 12
Total with taxes and fees
Turtle Cove – Lakefront & Indoor Pool!
Indoor pool
Sunset Spectacular – Waterfront & Indoor Pool!

Condo in Village of Four Seasons

Sunset Spectacular – Waterfront & Indoor Pool!
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.
$272 nightly
The price is $278
Jan 11 - Jan 12
Total with taxes and fees
Sunset Spectacular – Waterfront & Indoor Pool!
Pool
Lakeside Paradise - Waterfront, Pools, & Pickleball!

Condo in Lake Ozark

Lakeside Paradise - Waterfront, Pools, & Pickleball!
9.6 out of 10, Exceptional, (5)
"This condo was amazing!!! Had everything we needed, would highly recommend!!"
United States
Kathryn H.
$272 nightly
The price is $278
Jan 11 - Jan 12
Total with taxes and fees
Lakeside Paradise - Waterfront, Pools, & Pickleball!
Smart TV, fireplace
Waterfront Cozy Cove Retreat - LOTO Escape, Remodeled Comfort, Close to the Fun

Condo in Lake Ozark

Waterfront Cozy Cove Retreat - LOTO Escape, Remodeled Comfort, Close to the Fun
2.5 star property
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.
$276 nightly
The price is $284
Jan 10 - Jan 11
Total with taxes and fees
Waterfront Cozy Cove Retreat - LOTO Escape, Remodeled Comfort, Close to the Fun
Outdoor dining
Top Floor 2Bd 2Bath Condo at Lighthouse Landing!

Condo in Lake Ozark

Top Floor 2Bd 2Bath Condo at Lighthouse Landing!
2.0 star property
9.4 out of 10, Exceptional, (6)
"Excellent accommodations and check-in and check-out were a breeze. Very pleased with entire trip. "
United States
Nick A.
$312 nightly
The price is $335
Jan 11 - Jan 12
Total with taxes and fees
Top Floor 2Bd 2Bath Condo at Lighthouse Landing!
Exterior
SALE! New Treetop, 2 pools, dock, hot tub!

Cabin in Lake Ozark

SALE! New Treetop, 2 pools, dock, hot tub!
2.0 star property
9.2 out of 10, Wonderful, (9)
"I will definitely stay there again. The home was beautiful. "
United States
Megan L.
$466 nightly
The price is $466
Jan 11 - Jan 12
Total with taxes and fees
SALE! New Treetop, 2 pools, dock, hot tub!
Exterior
Lake of the Ozarks North Shore Cabin on the quiet side of lake.

Cabin in Rocky Mount

Lake of the Ozarks North Shore Cabin on the quiet side of lake.
10.0 out of 10, Exceptional, (2)
"Great stay! Would definitely come back!"
United States
Mikeshei K.
$142 nightly
The price is $150
Jan 11 - Jan 12
Total with taxes and fees
Lake of the Ozarks North Shore Cabin on the quiet side of lake.
Pool
The Sunrise Suite – Waterfront Screened Balcony w/Pool!

Condo in Lake Ozark

The Sunrise Suite – Waterfront Screened Balcony w/Pool!
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.
$265 nightly
The price is $271
Jan 11 - Jan 12
Total with taxes and fees
The Sunrise Suite – Waterfront Screened Balcony w/Pool!
Property grounds
Water facing Condo on Horseshoe bend mins from the Strip avail PWC 12 X 28 Slips

Condo in Village of Four Seasons

Water facing Condo on Horseshoe bend mins from the Strip avail PWC 12 X 28 Slips
9.8 out of 10, Exceptional, (19)
"Well kept lake house in a great condo community, lots of activities for the family. Close to other restaurants & fun.Thanks for a great stay!"
United States
Matt A.
$150 nightly
The price is $163
Jan 16 - Jan 17
Total with taxes and fees
Water facing Condo on Horseshoe bend mins from the Strip avail PWC 12 X 28 Slips
Smart TV, fireplace, stereo
Emerald Oasis - Waterfront, Pools, & Smoker!

Condo in Lake Ozark

Emerald Oasis - Waterfront, Pools, & Smoker!
10.0 out of 10, Exceptional, (6)
"Lovely property, Unit, & Location. Would stay again"
United States
Steven W.
$307 nightly
The price is $312
Jan 11 - Jan 12
Total with taxes and fees
Emerald Oasis - Waterfront, Pools, & Smoker!
Property grounds
Hideaway at Harbour Towne

Condo in Lake Ozark

Hideaway at Harbour Towne
2.5 star property
10.0 out of 10, Exceptional, (10)
"It was perfect for our girls getaway! "
United States
Cindy S.
$340 nightly
The price is $366
Jan 11 - Jan 12
Total with taxes and fees
Hideaway at Harbour Towne
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

Travelodge by Wyndham Jefferson City

Travelodge by Wyndham Jefferson City

10/10 Excellent
"The staff were very friendly and helpful. Hotel room was clean and it was not loud or crowded. I will coming back. "
Steven 2-night trip
Posted 1 day ago
Travelodge by Wyndham Jefferson City

Find out more about Olean

Everything you need to know about Olean vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Olean vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Olean vacation 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 low season months. For more hustle and bustle, you may prefer to visit Olean in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $286 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Olean rentals

At Expedia, we put the best Olean vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Olean?

Yes, you can find vacation rentals close to top local attractions in Olean, or you can go with a secluded option if you'd like a relaxing place to stay.

What's the top vacation rental in Olean?

Pet-Friendly Home In The Main Channel w/ Breathtaking Sunsets & Lake Views: This vacation home rental outside of Olean is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and a 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 Scenic Overlook Park. In the larger area, you’ll find Lake Ozark Speedway and Osage National Golf Club.

What’s a vacation rental in Olean like?

Vacation rentals are private properties you can stay in for a long or short time in Olean. Vacation rentals feature amenities like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a family getaway.