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Olean Vacation Rentals

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Olean vacation rentals

1. “Clabe” one of the 5 Tiny Cabins on the Osage River

“Clabe” one of the 5 Tiny Cabins on the Osage River
Tuscumbia
10.0 out of 10, Exceptional, (3 reviews)
"It was a great quiet place to get away for a weekend."
United States
Kyle B.
$165 nightly
The price is $176
Sep 24 - Sep 25
Total with taxes and fees
“Clabe” one of the 5 Tiny Cabins on the Osage River
A natural landscape with a river and trees.

2. Great Cabin on Osage River in Tuscumbia, MO

Great Cabin on Osage River in Tuscumbia, MO
Tuscumbia
9.8 out of 10, Exceptional, (60 reviews)
"It is a very comfortable place to stay! "
United States
Amanda
$182 nightly
The price is $194
Sep 28 - Sep 29
Total with taxes and fees
Great Cabin on Osage River in Tuscumbia, MO
A covered outdoor seating area with a view of a marina and buildings.

3. Pool Access! Family Getaway on Lake of the Ozarks

Pool Access! Family Getaway on Lake of the Ozarks
3.0 star property
Lake Ozark
$304 nightly
The price is $324
Sep 24 - Sep 25
Total with taxes and fees
Pool Access! Family Getaway on Lake of the Ozarks
A floating hotel with multiple decks, surrounded by a lake and a forested hill.

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

Pinkies Paradise-3BD/2BA/Sleeps 8PP-Lake Ozark
Lake Ozark
10.0 out of 10, Exceptional, (5 reviews)
"Place was unique and had fun theming. "
United States
Meaghan
$180 nightly
The price is $185
Sep 24 - Sep 25
Total with taxes and fees
Pinkies Paradise-3BD/2BA/Sleeps 8PP-Lake Ozark

5. The Sunrise Suite – Waterfront Screened Balcony w/Pool!

The Sunrise Suite – Waterfront Screened Balcony w/Pool!
Lake Ozark
10.0 out of 10, Exceptional, (11 reviews)
"Is and another couple stayed for 3 nights and had a great time. It was close to all the places we wanted to see and nice restaurants."
United States
Dawn B.
$273 nightly
The price is $278
Sep 27 - Sep 28
Total with taxes and fees
The Sunrise Suite – Waterfront Screened Balcony w/Pool!

6. Lakeside Paradise - Waterfront, Pools, & Pickleball!

Lakeside Paradise - Waterfront, Pools, & Pickleball!
Lake Ozark
9.0 out of 10, Wonderful, (6 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
$272 nightly
The price is $278
Sep 24 - Sep 25
Total with taxes and fees
Lakeside Paradise - Waterfront, Pools, & Pickleball!

7. 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, (9 reviews)
"Easy to find and very clean and comfortable for a quick stay at the lake!"
United States
Justine Blythe B.
$145 nightly
The price is $153
Sep 27 - Sep 28
Total with taxes and fees
Lake of the Ozarks North Shore Cabin on the quiet side of lake.

8. Posh Penthouse-Top Floor, Waterfront, Pools, & Pickleball!

Posh Penthouse-Top Floor, Waterfront, Pools, & Pickleball!
Village of Four Seasons
10.0 out of 10, Exceptional, (10 reviews)
"Yes, everything was very nice! Our first time spending Thanksgiving at the lake!! We"ll definitely do it again ."
United States
marc g.
$289 nightly
The price is $297
Sep 24 - Sep 25
Total with taxes and fees
Posh Penthouse-Top Floor, Waterfront, Pools, & Pickleball!
A hotel room with a large bed, a breakfast tray with croissants, fruit, and juice, and a view of a body of water.

9. Stillwater Shores Lakefront 2bd/2BA Pool, Hot Tub 6PP

Stillwater Shores Lakefront 2bd/2BA Pool, Hot Tub 6PP
Village of Four Seasons
9.0 out of 10, Wonderful, (2 reviews)
"It was very clean the only downside was that there was no king size bed as advertised just two queen size other than that we would have gave it a five star"
United States
Jennifer D.
$260 nightly
The price is $266
Sep 24 - Sep 25
Total with taxes and fees
Stillwater Shores Lakefront 2bd/2BA Pool, Hot Tub 6PP
A dining area with a table set for six, a ceiling fan, macramé wall hangings, a sofa, and a view through a glass door.

10. Welcome to the HIPPY HAVEN nothing but good vibes

Welcome to the HIPPY HAVEN nothing but good vibes
Lake Ozark
9.4 out of 10, Exceptional, (3 reviews)
"Loved thr place and really enjoyed my stay! I appreciated coming to a nice place for a quick stay. Would definitely stay again."
United States
Kyle R.
$180 nightly
The price is $190
Sep 28 - Sep 29
Total with taxes and fees
Welcome to the HIPPY HAVEN nothing but good vibes
A lakeside property with a dock, outdoor seating, and a small building.

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

Beach Cabin #6, Private/Shared Beach - Cabin #6
Lake Ozark
10.0 out of 10, Exceptional, (2 reviews)
"We enjoyed our stay and Emily was fantastic!"
United States
Sean D.
$263 nightly
The price is $263
Oct 1 - Oct 2
Total with taxes and fees
Beach Cabin #6, Private/Shared Beach - Cabin #6

12. Luxury Island Penthouse - Waterfront, Pool and Deck!

Luxury Island Penthouse - Waterfront, Pool and Deck!
Rocky Mount
9.8 out of 10, Exceptional, (16 reviews)
"I go to the Ozarks every summer and this is hands down the best condo we have ever stayed in. Beautiful open condo with amazing views."
United States
Joe A.
$311 nightly
The price is $317
Sep 24 - Sep 25
Total with taxes and fees
Luxury Island Penthouse - Waterfront, Pool and Deck!
A lake with docks and boats, surrounded by buildings and greenery.

13. 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, (29 reviews)
"Excellent place for a nice little getaway!"
United States
Stephanie L.
$163 nightly
The price is $175
Sep 27 - Sep 28
Total with taxes and fees
Cozy 1-bedroom condo in charming Village of Four Seasons with WiFi, fitness room
A stone wall, a door, and a window with a number 5 sign.

14. 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, (26 reviews)
"The host was super nice and always responded within minutes, the place was clean and had everything we needed, such a cute and cozy place to stay in the Ozarks I recommend!"
United States
Ashlyn C.
$122 nightly
The price is $130
Oct 10 - Oct 11
Total with taxes and fees
Cozy 1-bedroom condo with WiFi, AC in peaceful Lake Ozark. Prime location on 4MM
An indoor swimming pool with a lounge area, ceiling fans, and a green wall.

15. Bright & Cozy Condo with Lake, Private Balcony Views & Community Pool Retreat

Bright & Cozy Condo with Lake, Private Balcony Views & Community Pool Retreat
Lake Ozark
$147 nightly
The price is $157
Sep 24 - Sep 25
Total with taxes and fees
Bright & Cozy Condo with Lake, Private Balcony Views & Community Pool Retreat

16. Sunset Spectacular – Waterfront & Indoor Pool!

Sunset Spectacular – Waterfront & Indoor Pool!
Village of Four Seasons
10.0 out of 10, Exceptional, (5 reviews)
"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
Sep 24 - Sep 25
Total with taxes and fees
Sunset Spectacular – Waterfront & Indoor Pool!
A covered deck with wooden chairs and tables, a sign reading 'what happens at the lake is laughed about all year,' and a view of a lake.

17. Peaceful 2 bedroom Condo with NO Cleaning Fees on the Lake of the Ozarks

Peaceful 2 bedroom Condo with NO Cleaning Fees on the Lake of the Ozarks
Lake Ozark
10.0 out of 10, Exceptional, (73 reviews)
"Excellent property with an awesome host. Great communication from the begining,very quiet and comfortable accommodations! Will stay again!"
United States
Chris
$120 nightly
The price is $129
Oct 4 - Oct 5
Total with taxes and fees
Peaceful 2 bedroom Condo with NO Cleaning Fees on the Lake of the Ozarks
An aerial view of a lakeside hotel with multiple docked boats, a central building with a tall chimney, and a parking area surrounded by trees.

18. 3MM, fully remolded, main channel lakefront with pool

3MM, fully remolded, main channel lakefront with pool
Lake Ozark
10.0 out of 10, Exceptional, (52 reviews)
"Great weekend getaway. "
United States
Lawrence H.
$295 nightly
The price is $312
Sep 28 - Sep 29
Total with taxes and fees
3MM, fully remolded, main channel lakefront with pool
A deck with a table set for two, overlooking a body of water, with a covered area and lounge chairs.

19. Adventure West-Lakefront 1BD/1BA/Indoor/Outdoor Pool/Hottub/Pickleball-4PP

Adventure West-Lakefront 1BD/1BA/Indoor/Outdoor Pool/Hottub/Pickleball-4PP
Village of Four Seasons
9.0 out of 10, Wonderful, (6 reviews)
"Very polite and helpful I will most definitely book them again"
United States
LaToasha B.
$243 nightly
The price is $248
Sep 24 - Sep 25
Total with taxes and fees
Adventure West-Lakefront 1BD/1BA/Indoor/Outdoor Pool/Hottub/Pickleball-4PP
A covered outdoor deck with a glass table, chairs, and a sofa.

20. 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
9.6 out of 10, Exceptional, (7 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
Sep 24 - Sep 25
Total with taxes and fees
Lake of the Ozarks Condo with Main Channel Views - boat slip available
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

Days Inn by Wyndham Osage Beach Lake of the Ozarks

Days Inn by Wyndham Osage Beach Lake of the Ozarks

8/10 Good
"all was good"
mitchell 1-night trip
Posted 13 hours ago
Days Inn by Wyndham Osage Beach Lake of the Ozarks

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 $129 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 - The best in Luxury living at the lake - POOL currently in const...: 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 Lick Branch Cove. In the larger area, you’ll find Lake of the Ozarks and Bagnell Dam Viewpoint and Bagnell Dam.

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.