Olean Vacation Rentals

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Vacation Rentals in Olean

The Carriage House at Parker's Place

Jefferson City
10.0 out of 10, Exceptional, (44)
"Great place!!! So clean! Loved our stay. "
United States
adrianne c.
$273 nightly
The price is $273
Nov 17 - Nov 18
Total with taxes and fees
The Carriage House at Parker's Place

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

Jefferson City
9.6 out of 10, Exceptional, (28)
"Great place for a single or a couple for a getaway."
United States
joe f.
$157 nightly
The price is $163
Nov 18 - Nov 19
Total with taxes and fees
Business or Pleasure - a perfect and cozy get-away!

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

Lake Ozark
9.8 out of 10, Exceptional, (10)
"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
$174 nightly
The price is $180
Nov 17 - Nov 18
Total with taxes and fees
Lakefront Condo, 2 Bed, 2 Bath-Sleeps 6, Pool, Hot Tub, Tennis Courts, Swim Dock, WIFI

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

Tuscumbia
10.0 out of 10, Exceptional, (1)
"What a fantastic find! As a spontaneous planner, I was grateful to find this river front property. The listing mention a shower house which led to overpacking, but pleasantly surprised how well equipped the accommodation with anything I could possibly need and with unique and thoughtful experience the owners created truly made you feel like family impressed not just a stay but an experience money can’t buy so thank you "
United States
Laura K.
$165 nightly
The price is $175
Nov 17 - Nov 18
Total with taxes and fees
“Delbert” one of the 5 Tiny Cabins on the Osage River

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, (26)
"This property was amazing. Clean, spacious, cute! "
United States
Danielle S.
$284 nightly
The price is $297
Nov 17 - Nov 18
Total with taxes and fees
The Big House, Historic 4-Bedroom Home With Custom Art And Dedicated Workspace

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
$281 nightly
The price is $297
Nov 28 - Nov 29
Total with taxes and fees
Balcony w/ Marina Views: Lake Ozark Hideaway!

Luxury Lake of the Ozarks Getaway with Dock, Launch Ramp & Autumn Views

Lake Ozark
9.8 out of 10, Exceptional, (125)
"Nice house on a quiet cove! Kitchen has all of the utensils and pans that you need to cook with. Beds were comfy as well!"
United States
Kevin T.
$667 nightly
The price is $706
Nov 30 - Dec 1
Total with taxes and fees
Luxury Lake of the Ozarks Getaway with Dock, Launch Ramp & Autumn Views

Lakefront cozy cottage!

2.0 star property
Rocky Mount
9.6 out of 10, Exceptional, (10)
"Check in was quick and easy the house was super cute and clean we had a great time!"
United States
Renee W.
$347 nightly
The price is $365
Nov 17 - Nov 18
Total with taxes and fees
Lakefront cozy cottage!

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

Lake Ozark
9.8 out of 10, Exceptional, (22)
"It was an amazing experience, the house has all the facilities, well decorated, full of natural light, perfect location. I highly recommend to rent this house!"
United States
Sofía C.
$302 nightly
The price is $316
Nov 17 - Nov 18
Total with taxes and fees
Our Cove Retreat - Perfect for Wave-Free Swimming, Tanning & Prime Location Fun!

Lake Life Location with Serenity

Osage Beach
9.8 out of 10, Exceptional, (16)
"Relaxing and peaceful "
United States
Virginia R.
Lake Life Location with Serenity

Lake Ozark-1BD/1BA-Hippo Pool, Regalia Resort, Gym, Hottub, Pool-Sleeps 2PP

Lake Ozark
8.0 out of 10, Very Good, (1)
"Cute and clean. No A/C, so it was pretty hot. 2 small fans and a ceiling fan isn't enough. The bed was soft....too soft. Kind of sank in. The Hippo pool closed because of a storm. So that sucked."
United States
Megan H.
$157 nightly
The price is $157
Nov 17 - Nov 18
Total with taxes and fees
Lake Ozark-1BD/1BA-Hippo Pool, Regalia Resort, Gym, Hottub, Pool-Sleeps 2PP

Treetop Village12-2Bed/3Bath/Lakefront/Lakeview/Pools/Dock/6-8PP-Four Seasons Area

Village of Four Seasons
8.0 out of 10, Very Good, (1)
"The property was great with all the lush foliage and lake front spot. The pools were so fun! Swimming dock was enjoyed. The cabin was outdated but we knew that when we booked. Suited our needs. We had an issue after checking in, but it was resolved quickly by staff. Thanks for letting us stay! We will be back"
United States
Jade W.
$291 nightly
The price is $297
Nov 17 - Nov 18
Total with taxes and fees
Treetop Village12-2Bed/3Bath/Lakefront/Lakeview/Pools/Dock/6-8PP-Four Seasons Area

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

Osage Beach
10.0 out of 10, Exceptional, (84)
"Great views! Loved our stay!"
United States
Douglas K.
$242 nightly
The price is $259
Nov 19 - Nov 20
Total with taxes and fees
Stylish Lakefront, King Bed Suite, Sunset View, Pool, Boat Slip, PrivateTopFloor

Lake of the Ozarks North Shore Cabin on the quiet side of lake.

Rocky Mount
10.0 out of 10, Exceptional, (2)
"Overnight stay in a clean and comfortable room"
United States
renee w.
$142 nightly
The price is $150
Nov 17 - Nov 18
Total with taxes and fees
Lake of the Ozarks North Shore Cabin on the quiet side of lake.

3 Bedroom Osage Beach Condo w/ Pool & Main Channel Views

2.0 star property
Osage Beach
10.0 out of 10, Exceptional, (3)
"We had a great family vacation. The condo fit our needs perfectly and had everything we needed and more. The amenities-pool, cornhole, and dock access were very nice and kept my kids busy. Very fun area to visit!"
United States
Erica M.
$380 nightly
The price is $395
Nov 17 - Nov 18
Total with taxes and fees
3 Bedroom Osage Beach Condo w/ Pool & Main Channel Views

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.
$514 nightly
The price is $514
Nov 18 - Nov 19
Total with taxes and fees
4 Bedroom Comfortable Cottage

Charming cabin with WiFi and AC in delightful Eldon

Eldon
9.0 out of 10, Wonderful, (7)
"The photos don’t do this cabin and property justice! The cabin is so cozy, warm, and inviting! The property is quiet and peaceful with plenty of natural beauty. Lots of wild flowers all around during our stay. Sitting on the porch swing was a nice relaxing experience especially while stargazing! And movie nights on the very comfortable couch and the electric fireplace providing a nice ambiance was one of our favorite moments during our stay! Would definitely recommend this cabin to anyone...
United States
Bradley L.
$150 nightly
The price is $161
Nov 17 - Nov 18
Total with taxes and fees
Charming cabin with WiFi and AC in delightful Eldon

Breathtaking Views - Two Pools - Enclosed Balcony

Lake Ozark
9.8 out of 10, Exceptional, (18)
"We enjoyed our stay and the beautiful view."
United States
Heather L.
$420 nightly
The price is $438
Nov 17 - Nov 18
Total with taxes and fees
Breathtaking Views - Two Pools - Enclosed Balcony

Cozy, Yet Spacious Condo, Hot Tub/Indoor Pool, Close to Everything

Lake Ozark
9.4 out of 10, Exceptional, (17)
"Very nice accommodations. Really enjoyed our stay"
United States
Edward G.
$236 nightly
The price is $243
Nov 17 - Nov 18
Total with taxes and fees
Cozy, Yet Spacious Condo, Hot Tub/Indoor Pool, Close to Everything

Wonderful Remote Lake Cabin! Fish from Deck & Dock

Rocky Mount
9.8 out of 10, Exceptional, (11)
"A nice property for a quiet family get away in the Ozarks. Lots to do inside the house and back yard was right on the water!"
United States
Sean H.
$436 nightly
The price is $455
Nov 17 - Nov 18
Total with taxes and fees
Wonderful Remote Lake Cabin! Fish from Deck & Dock
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 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 $326 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.

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?

Lake Of The Ozarks ~ Great Family Rental With The Best View On The Lake! : This vacation home rental outside of Olean is located on a lake and has a fireplace, a patio, 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. Make the most of the foosball table in this rental home to help you unwind.

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 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.