Olean Vacation Rentals

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Our top choices for Olean vacation rentals

Historic Carriage House in Jefferson City Near Capitol & Old Penitentiary

Historic Carriage House in Jefferson City Near Capitol & Old Penitentiary
Jefferson City
10.0 out of 10, Exceptional, (50 reviews)
"Excellent stay! Charming house. Great location. Perfect for an extended stay."
United States
Ellen R.
$297 nightly
The price is $317
May 24 - May 25
Total with taxes and fees
Historic Carriage House in Jefferson City Near Capitol & Old Penitentiary

Newly remodeled updated condo,12x32 Boat slip, wi-Fi Internet cable TV, pwc slip

Newly remodeled updated condo,12x32 Boat slip, wi-Fi Internet cable TV, pwc slip
Lake Ozark
10.0 out of 10, Exceptional, (83 reviews)
"Great place!"
United States
J.D. L.
$369 nightly
The price is $400
May 24 - May 25
Total with taxes and fees
Newly remodeled updated condo,12x32 Boat slip, wi-Fi Internet cable TV, pwc slip

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

The Big House, Historic 4-Bedroom Home With Custom Art And Dedicated Workspace
Jefferson City
10.0 out of 10, Exceptional, (35 reviews)
"Very spacious, has everything a big family needs for a place to stay. Will definitely consider it next time again."
United States
ALVIN
$281 nightly
The price is $301
May 18 - May 19
Total with taxes and fees
The Big House, Historic 4-Bedroom Home With Custom Art And Dedicated Workspace

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

Stylish Lakefront, King Bed Suite, Sunset View, Pool, Boat Slip, PrivateTopFloor
Osage Beach
10.0 out of 10, Exceptional, (97 reviews)
"Beautiful place to stay! Great location, comfortable beds, games to play and nice living room to lounge with the family- or in nicer weather enjoy the deck with the beautiful views. I had a couple of questions and owners responded immediately (even from Thailand) We will keep this place saved for our next trip to the lake. "
United States
Jennifer S.
$276 nightly
The price is $296
May 20 - May 21
Total with taxes and fees
Stylish Lakefront, King Bed Suite, Sunset View, Pool, Boat Slip, PrivateTopFloor

Regatta Bay Getaway-Luxury Lakefront Condo/2BD/2BA/Deck/Pool/Dock-6PP

Regatta Bay Getaway-Luxury Lakefront Condo/2BD/2BA/Deck/Pool/Dock-6PP
Lake Ozark
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful condo, great location on the lake. Would stay again in a heartbeat"
United States
Nick C.
$357 nightly
The price is $370
May 18 - May 19
Total with taxes and fees
Regatta Bay Getaway-Luxury Lakefront Condo/2BD/2BA/Deck/Pool/Dock-6PP

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

Our Cove Retreat - Perfect for Wave-Free Swimming, Tanning & Prime Location Fun!
Lake Ozark
9.8 out of 10, Exceptional, (27 reviews)
"Great place!"
United States
Amber M.
$368 nightly
The price is $395
May 19 - May 20
Total with taxes and fees
Our Cove Retreat - Perfect for Wave-Free Swimming, Tanning & Prime Location Fun!

Treetop Vibes on Horseshoe Bend

Treetop Vibes on Horseshoe Bend
Lake Ozark
9.2 out of 10, Wonderful, (12 reviews)
"Great time, beautiful property, everything was perfect! Will definitely be back. "
United States
Lydia B.
$374 nightly
The price is $404
May 18 - May 19
Total with taxes and fees
Treetop Vibes on Horseshoe Bend

Amazing Lakefront Pool On Coveted Horseshoe Bend!

Amazing Lakefront Pool On Coveted Horseshoe Bend!
Four Seasons
9.2 out of 10, Wonderful, (12 reviews)
"Beautiful Property, great location!"
United States
Allan M.
$370 nightly
The price is $398
May 18 - May 19
Total with taxes and fees
Amazing Lakefront Pool On Coveted Horseshoe Bend!

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

Business or Pleasure - a perfect and cozy get-away!
Jefferson City
9.6 out of 10, Exceptional, (32 reviews)
"Perfect place to stay for my trip"
United States
Joshua B.
$157 nightly
The price is $167
May 19 - May 20
Total with taxes and fees
Business or Pleasure - a perfect and cozy get-away!

SALE! Lakefront | 4 Pools | Dock | Sauna | +Resort

SALE! Lakefront | 4 Pools | Dock | Sauna | +Resort
Lake Ozark
9.4 out of 10, Exceptional, (13 reviews)
"Photos and description were accurate. Great value. "
United States
micah
$490 nightly
The price is $490
May 27 - May 28
Total with taxes and fees
SALE! Lakefront | 4 Pools | Dock | Sauna | +Resort

Lakefront cozy cottage!

Lakefront cozy cottage!
Rocky Mount
9.8 out of 10, Exceptional, (13 reviews)
"Comfortable stay, great fishing and kids loved swimming off the dock! "
United States
Jessica H.
$297 nightly
The price is $313
May 18 - May 19
Total with taxes and fees
Lakefront cozy cottage!

Hideaway at Harbour Towne

Hideaway at Harbour Towne
Lake Ozark
10.0 out of 10, Exceptional, (10 reviews)
"It was perfect for our girls getaway! "
United States
Cindy S.
$342 nightly
The price is $368
May 18 - May 19
Total with taxes and fees
Hideaway at Harbour Towne

Charming cabin with WiFi and AC in delightful Eldon

Charming cabin with WiFi and AC in delightful Eldon
Eldon
9.4 out of 10, Exceptional, (12 reviews)
"The cabin was nice was clean and wonderful views"
United States
JEREMY
$150 nightly
The price is $158
May 18 - May 19
Total with taxes and fees
Charming cabin with WiFi and AC in delightful Eldon

Feel right at home in this family-sized new listing at the 1MM on the Lake!

Feel right at home in this family-sized new listing at the 1MM on the Lake!
Lake Ozark
10.0 out of 10, Exceptional, (5 reviews)
"We thoroughly enjoyed our stay at Lake Ozark. The location and living space were perfect for our large group. The screened in patio was our favorite feature! "
United States
Erika C.
$432 nightly
The price is $457
May 18 - May 19
Total with taxes and fees
Feel right at home in this family-sized new listing at the 1MM on the Lake!

Bogey Bungalow-Four Seasons-1BD/1BA/Balcony/Pool/Golf-2PP

Bogey Bungalow-Four Seasons-1BD/1BA/Balcony/Pool/Golf-2PP
Lake Ozark
10.0 out of 10, Exceptional, (2 reviews)
"Will definitely be staying there again! "
United States
Thomas
$186 nightly
The price is $193
May 18 - May 19
Total with taxes and fees
Bogey Bungalow-Four Seasons-1BD/1BA/Balcony/Pool/Golf-2PP

Lake of the Ozarks Condo with Main Channel Views - boat slip available

Lake of the Ozarks Condo with Main Channel Views - boat slip available
Rocky Mount
10.0 out of 10, Exceptional, (4 reviews)
"Great condo overlooking the lake! This place was great for a family and had everything you would need for an enjoyable stay!"
United States
Tiffany V.
$377 nightly
The price is $397
May 19 - May 20
Total with taxes and fees
Lake of the Ozarks Condo with Main Channel Views - boat slip available

Lake-Life Condo close to Attractions & LOZ strip

Lake-Life Condo close to Attractions & LOZ strip
Lake Ozark
9.4 out of 10, Exceptional, (14 reviews)
"We had a truly wonderful stay at this condo! Everything was exactly as advertised—clean, well-equipped, and incredibly comfortable. The space was thoughtfully decorated and felt like a home away from home."
United States
Michele B.
$305 nightly
The price is $323
May 18 - May 19
Total with taxes and fees
Lake-Life Condo close to Attractions & LOZ strip

Cozy 1-bedroom condo with WiFi, AC in peaceful Lake Ozark. Prime location on 4MM

Cozy 1-bedroom condo with WiFi, AC in peaceful Lake Ozark. Prime location on 4MM
Lake Ozark
10.0 out of 10, Exceptional, (19 reviews)
"Very happy with our stay, and the great communication with our host. "
United States
Greg K.
$143 nightly
The price is $151
May 19 - May 20
Total with taxes and fees
Cozy 1-bedroom condo with WiFi, AC in peaceful Lake Ozark. Prime location on 4MM

Executive 2 Bedroom Condo. Amazing Lakefront Views. Top Floor. No stairs.

Executive 2 Bedroom Condo. Amazing Lakefront Views. Top Floor. No stairs.
Osage Beach
10.0 out of 10, Exceptional, (239 reviews)
"Our host was great with communication and would love to stay there in the future."
United States
Charles I.
$323 nightly
The price is $347
Jun 8 - Jun 9
Total with taxes and fees
Executive 2 Bedroom Condo. Amazing Lakefront Views. Top Floor. No stairs.

Unit 4 On the Strip! Lake Ozark Gem w/ Pool Access

Unit 4 On the Strip! Lake Ozark Gem w/ Pool Access
3.0 star property
Lake Ozark
$455 nightly
The price is $496
May 22 - May 23
Total with taxes and fees
Unit 4 On the Strip! Lake Ozark Gem w/ Pool Access
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 $160 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?

Cozy lake in front of the home: This vacation home rental outside of Olean is located on a lake and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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 Lick Branch Cove. In the larger area, you’ll find Osage National Golf Course and Lake of the Ozarks and Bagnell Dam Viewpoint.

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.