Olean Vacation Rentals

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Our top choices for Olean vacation rentals

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 18 - May 19
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, (12 reviews)
"The cabin was nice was clean and wonderful views"
United States
JEREMY
$150 nightly
The price is $158
May 14 - May 15
Total with taxes and fees
Charming cabin with WiFi and AC in delightful Eldon

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.
$270 nightly
The price is $289
May 17 - May 18
Total with taxes and fees
Historic Carriage House in Jefferson City Near Capitol & Old Penitentiary

Beach Cabin #6, Private/Shared Beach - Cabin #6

Beach Cabin #6, Private/Shared Beach - Cabin #6
Lake Ozark
$231 nightly
The price is $231
Jun 11 - Jun 12
Total with taxes and fees
Beach Cabin #6, Private/Shared Beach - Cabin #6

Fairway To Heaven-Four Seasons Condo 2BD/2BA/Deck/Pool/Golf/Firepit-6PP

Fairway To Heaven-Four Seasons Condo 2BD/2BA/Deck/Pool/Golf/Firepit-6PP
Lake Ozark
9.0 out of 10, Wonderful, (11 reviews)
"Great balcony view, great amenities, clean and quiet, perfect for my entire family. Would easily stay again!"
United States
Joseph B.
$490 nightly
The price is $497
May 13 - May 14
Total with taxes and fees
Fairway To Heaven-Four Seasons Condo 2BD/2BA/Deck/Pool/Golf/Firepit-6PP

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
May 13 - May 14
Total with taxes and fees
Turtle Cove – Lakefront & Indoor Pool!

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, (7 reviews)
"Wonderful! Extremely child & pet friendly. We traveled with our 5 children and could not have asked for a more perfect place. Highly recommended. "
United States
Jacquelyn
$342 nightly
The price is $386
May 28 - May 29
Total with taxes and fees
Historic 4-bedroom pet friendly rental close to downtown.

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, (5 reviews)
"Great place. Very clean and everything you could need. Would definitely stay again!"
United States
Josh L.
$145 nightly
The price is $153
May 13 - May 14
Total with taxes and fees
Lake of the Ozarks North Shore Cabin on the quiet side of lake.

Cedar Sanctuary #17-2BD/2BA/Pools/Grill/Dock-4PP

Cedar Sanctuary #17-2BD/2BA/Pools/Grill/Dock-4PP
Village of Four Seasons
10.0 out of 10, Exceptional, (2 reviews)
"Everything was great!"
United States
Jeffrey B.
$275 nightly
The price is $282
May 13 - May 14
Total with taxes and fees
Cedar Sanctuary #17-2BD/2BA/Pools/Grill/Dock-4PP

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
$200 nightly
The price is $207
May 13 - May 14
Total with taxes and fees
Pinkies Paradise-3BD/2BA/Sleeps 8PP-Lake Ozark

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
$319 nightly
The price is $341
Jun 2 - Jun 3
Total with taxes and fees
The Big House, Historic 4-Bedroom Home With Custom Art And Dedicated Workspace

Treetop VIllage Four Seasons #10-Lakefront/2BD/3BA/Pools/Grill/Dock-4PP

Treetop VIllage Four Seasons #10-Lakefront/2BD/3BA/Pools/Grill/Dock-4PP
Village of Four Seasons
8.0 out of 10, Very Good, (6 reviews)
"Communication was a little difficulty at times but overall we loved our time here!"
United States
Kelley H.
$233 nightly
The price is $241
May 13 - May 14
Total with taxes and fees
Treetop VIllage Four Seasons #10-Lakefront/2BD/3BA/Pools/Grill/Dock-4PP

Lakeside Paradise - Waterfront, Pools, & Pickleball!

Lakeside Paradise - Waterfront, Pools, & Pickleball!
Lake Ozark
9.6 out of 10, Exceptional, (5 reviews)
"Place was impeccable and the view was spectacular. Great location. In the middle of everything. Property was so clean and cozy. Will definitely be coming back. Would definitely recommend staying at the property 10/10."
United States
april ann
$273 nightly
The price is $279
May 13 - May 14
Total with taxes and fees
Lakeside Paradise - Waterfront, Pools, & Pickleball!

Hideaway in the Trees-#30-Lakefront/2BD/3BA/Pools/Grill/Dock-4PP

Hideaway in the Trees-#30-Lakefront/2BD/3BA/Pools/Grill/Dock-4PP
Village of Four Seasons
9.4 out of 10, Exceptional, (8 reviews)
"The host was communicative, the house was in a great spot, and was very unique. We will definitely come back!"
United States
Sabrena M.
$291 nightly
The price is $300
May 13 - May 14
Total with taxes and fees
Hideaway in the Trees-#30-Lakefront/2BD/3BA/Pools/Grill/Dock-4PP

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
9.6 out of 10, Exceptional, (14 reviews)
"The place was nice and the host was helpful. "
United States
Nathan R.
$164 nightly
The price is $176
May 26 - May 27
Total with taxes and fees
Cozy 1-bedroom condo in charming Village of Four Seasons with WiFi, fitness room

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
May 13 - May 14
Total with taxes and fees
Summer Serenity Waterfront Condo!- Indoor Pool!

Cozy 1-bedroom condo with Lake View no steps in the heart of town

Cozy 1-bedroom condo with Lake View no steps in the heart of town
Osage Beach
10.0 out of 10, Exceptional, (4 reviews)
"It was a great place to stay with an amazing view. The host was very helpful and great with communication. We will definitely be back to stay!"
United States
Rachel B.
$149 nightly
The price is $160
May 13 - May 14
Total with taxes and fees
Cozy 1-bedroom condo with Lake View no steps in the heart of town

Cozy Cabin on the Lake! Sleeps 2 @ Jacks Shack!

Cozy Cabin on the Lake! Sleeps 2 @ Jacks Shack!
Osage Beach
9.8 out of 10, Exceptional, (7 reviews)
"Comfortable and cozy!Right on the water and able to walk to backwater jacks ! "
United States
Jeff G.
$275 nightly
The price is $295
May 13 - May 14
Total with taxes and fees
Cozy Cabin on the Lake! Sleeps 2 @ Jacks Shack!

Lakefront - King Bed - Views - 3 Pools - 2BR/2BA

Lakefront - King Bed - Views - 3 Pools - 2BR/2BA
Osage Beach
10.0 out of 10, Exceptional, (32 reviews)
"Clean and comfortable place to stay while working in Osage Beach. "
United States
Johnna S.
$279 nightly
The price is $300
May 16 - May 17
Total with taxes and fees
Lakefront - King Bed - Views - 3 Pools - 2BR/2BA

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.
$308 nightly
The price is $334
May 16 - May 17
Total with taxes and fees
Newly remodeled updated condo,12x32 Boat slip, wi-Fi Internet cable TV, pwc slip
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.