Olean Vacation Rentals

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Our top choices for Olean vacation rentals

The Carriage House at Parker's Place

The Carriage House at Parker's Place
Jefferson City
10.0 out of 10, Exceptional, (46 reviews)
"Such a cool place to stay. My husband and I stayed here on our wedding night. It was super nice and clean. Would definitely stay again. "
United States
Mackenzie A.
$272 nightly
The price is $291
Mar 5 - Mar 6
Total with taxes and fees
The Carriage House at Parker's Place

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, (29 reviews)
"Perfect place to stay for my trip"
United States
Joshua B.
$157 nightly
The price is $167
Mar 3 - Mar 4
Total with taxes and fees
Business or Pleasure - a perfect and cozy get-away!

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, (11 reviews)
"Wonderful cabin. Absolutely recommend!!"
United States
Vivian
$150 nightly
The price is $158
Mar 2 - Mar 3
Total with taxes and fees
Charming cabin with WiFi and AC in delightful Eldon

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

“Harold” one of the 5 Tiny Cabins on the Osage River
Tuscumbia
8.0 out of 10, Very Good, (1 review)
"Lovely location. Room exceptionally clean. "
United States
Tanya R.
$165 nightly
The price is $175
Mar 2 - Mar 3
Total with taxes and fees
“Harold” one of the 5 Tiny Cabins on the Osage River

Cozy 1-bedroom condo in charming Village of Four Seasons with WiFi, fitness room

Cozy 1-bedroom condo in charming Village of Four Seasons with WiFi, fitness room
Village of Four Seasons
9.4 out of 10, Exceptional, (11 reviews)
"Condo was just as expected and in a great location!"
United States
Ashley R.
$164 nightly
The price is $176
Mar 2 - Mar 3
Total with taxes and fees
Cozy 1-bedroom condo in charming Village of Four Seasons with WiFi, fitness room

Historic 4-bedroom pet friendly rental close to downtown.

Historic 4-bedroom pet friendly rental close to downtown.
Jefferson City
10.0 out of 10, Exceptional, (3 reviews)
"If you're looking for great, comforting and warm accommodations of an historic amply spaced home with the modern updates of today's world look no further!!! Plus, they have all the extra home amenities that a hotel could not even begin to provide! My family came to Jefferson City for a loved ones funeral and the sweet, responsive owners even left us a kind note and caring card. We've already recommended their location as a great place to stay to others and would absolutely book for ourselves...
United States
Jennifer
$296 nightly
The price is $335
Mar 22 - Mar 23
Total with taxes and fees
Historic 4-bedroom pet friendly rental close to downtown.

Lake Life Location with Serenity

Lake Life Location with Serenity
Osage Beach
9.8 out of 10, Exceptional, (16 reviews)
"Beautiful condo, excellent location."
United States
Amy R.
Lake Life Location with Serenity

Pinkies Paradise-3BD/2BA/Sleeps 8PP-Lake Ozark

Pinkies Paradise-3BD/2BA/Sleeps 8PP-Lake Ozark
Lake Ozark
10.0 out of 10, Exceptional, (4 reviews)
"Place was unique and had fun theming. "
United States
Meaghan
$167 nightly
The price is $172
Mar 2 - Mar 3
Total with taxes and fees
Pinkies Paradise-3BD/2BA/Sleeps 8PP-Lake Ozark

Water facing Condo on Horseshoe bend mins from the Strip avail PWC 12 X 28 Slips

Water facing Condo on Horseshoe bend mins from the Strip avail PWC 12 X 28 Slips
Village of Four Seasons
9.8 out of 10, Exceptional, (19 reviews)
"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.
$216 nightly
The price is $231
Mar 2 - Mar 3
Total with taxes and fees
Water facing Condo on Horseshoe bend mins from the Strip avail PWC 12 X 28 Slips

Summer Serenity Waterfront Condo!- Indoor Pool!

Summer Serenity Waterfront Condo!- Indoor Pool!
ake ozark mo
9.6 out of 10, Exceptional, (13 reviews)
"Great location!"
United States
Melissa F.
$278 nightly
The price is $285
Mar 2 - Mar 3
Total with taxes and fees
Summer Serenity Waterfront Condo!- Indoor Pool!

Lakeside Paradise - Waterfront, Pools, & Pickleball!

Lakeside Paradise - Waterfront, Pools, & Pickleball!
Lake Ozark
9.6 out of 10, Exceptional, (5 reviews)
"This condo was amazing!!! Had everything we needed, would highly recommend!!"
United States
Kathryn H.
$273 nightly
The price is $279
Mar 2 - Mar 3
Total with taxes and fees
Lakeside Paradise - Waterfront, Pools, & Pickleball!

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, (14 reviews)
"Very happy with our stay, and the great communication with our host. "
United States
Greg K.
$119 nightly
The price is $126
Mar 2 - Mar 3
Total with taxes and fees
Cozy 1-bedroom condo with WiFi, AC in peaceful Lake Ozark. Prime location on 4MM

Turtle Cove – Lakefront & Indoor Pool!

Turtle Cove – Lakefront & Indoor Pool!
Village of Four Seasons
9.6 out of 10, Exceptional, (7 reviews)
"We had a wonderful relaxing stay. The condo was perfect."
United States
Kasie W.
$273 nightly
The price is $279
Mar 2 - Mar 3
Total with taxes and fees
Turtle Cove – Lakefront & Indoor Pool!

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.
$275 nightly
The price is $282
Mar 2 - Mar 3
Total with taxes and fees
Regatta Bay Getaway-Luxury Lakefront Condo/2BD/2BA/Deck/Pool/Dock-6PP

Stunning Views, Inviting Pools, and Endless Fun!

Stunning Views, Inviting Pools, and Endless Fun!
Osage Beach
9.8 out of 10, Exceptional, (12 reviews)
"Super cute place and a great location, perfect for our girls getaway! "
United States
Stacey M.
$514 nightly
The price is $546
Mar 3 - Mar 4
Total with taxes and fees
Stunning Views, Inviting Pools, and Endless Fun!

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

SALE! Lakefront | 4 Pools | Dock | Sauna | +Resort
Lake Ozark
9.2 out of 10, Wonderful, (9 reviews)
"I will definitely stay there again. The home was beautiful. "
United States
Megan L.
$448 nightly
The price is $448
Mar 2 - Mar 3
Total with taxes and fees
SALE! Lakefront | 4 Pools | Dock | Sauna | +Resort

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, (88 reviews)
"Great place to stay with great view. Property managers were great and easy to contact, and quick to respond to us with a question we had. I would stay here again"
United States
Marcus B.
$233 nightly
The price is $249
Mar 4 - Mar 5
Total with taxes and fees
Stylish Lakefront, King Bed Suite, Sunset View, Pool, Boat Slip, PrivateTopFloor

Emerald Oasis - Waterfront, Pools, & Smoker!

Emerald Oasis - Waterfront, Pools, & Smoker!
Lake Ozark
10.0 out of 10, Exceptional, (6 reviews)
"Lovely property, Unit, & Location. Would stay again"
United States
Steven W.
$307 nightly
The price is $312
Mar 2 - Mar 3
Total with taxes and fees
Emerald Oasis - Waterfront, Pools, & Smoker!

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

Lake of the Ozarks North Shore Cabin on the quiet side of lake.
Rocky Mount
10.0 out of 10, Exceptional, (4 reviews)
"Great stay! Would definitely come back!"
United States
Mikeshei K.
$145 nightly
The price is $153
Mar 2 - Mar 3
Total with taxes and fees
Lake of the Ozarks North Shore Cabin on the quiet side of lake.

Lake Views, Lakefront Pool, Great Location!

Lake Views, Lakefront Pool, Great Location!
Lake Ozark
9.0 out of 10, Wonderful, (9 reviews)
"Great place for winter getaway."
United States
Robert M.
$252 nightly
The price is $267
Mar 3 - Mar 4
Total with taxes and fees
Lake Views, Lakefront Pool, Great Location!
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 $1,340 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?

Porto Cima - Amazing 6,500 SF Home - Private Heated Pool, Arcade, Sleeps 30 PLUS: This vacation home rental outside of Olean is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a balcony, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 Osage National Golf Club 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.