Default HTG hotel image

Olean Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Olean vacation rentals

A natural landscape with a river and trees.

1. 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
$172 nightly
The price is $184
Oct 20 - Oct 21
Total with taxes and fees
Great Cabin on Osage River in Tuscumbia, MO
The Cave

2. 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.
$268 nightly
The price is $273
Oct 20 - Oct 21
Total with taxes and fees
The Sunrise Suite – Waterfront Screened Balcony w/Pool!
A floating hotel with multiple decks, surrounded by a lake and a forested hill.

3. Tiki Time-2BD/2BA/Pools/Grill/Patio-Four Seasons

Tiki Time-2BD/2BA/Pools/Grill/Patio-Four Seasons
Lake Ozark
10.0 out of 10, Exceptional, (1 review)
"Everything was perfect for my granddaughters and I. Thank you"
United States
Brenda S.
$198 nightly
The price is $203
Oct 20 - Oct 21
Total with taxes and fees
Tiki Time-2BD/2BA/Pools/Grill/Patio-Four Seasons
The Cave

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

Luxury Island Penthouse - Waterfront, Pool and Deck!
Rocky Mount
9.6 out of 10, Exceptional, (18 reviews)
"The place was amazing it was beautiful clean secluded and peaceful. I would definitely visit again . My only complaint is that it's a bit to secluded everything was far, and not much to do on the resort"
United States
Jaavonte
$308 nightly
The price is $313
Oct 20 - Oct 21
Total with taxes and fees
Luxury Island Penthouse - Waterfront, Pool and Deck!
The Cave

5. Lighthouse Retreat – Pool, Swim Dock and More!

Lighthouse Retreat – Pool, Swim Dock and More!
Lake Ozark
9.0 out of 10, Wonderful, (7 reviews)
"The unit was nice.The bathrooms could use a good deep cleaning. Lots of stairs to the lake, I think someone said at least 70 something. We loved the pool, bring your own beach towel and pool floats. Resident of the complex were very friendly."
United States
Scott B.
$268 nightly
The price is $273
Oct 20 - Oct 21
Total with taxes and fees
Lighthouse Retreat – Pool, Swim Dock and More!
The Cave

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

Lakeside Paradise - Waterfront, Pools, & Pickleball!
Lake Ozark
9.2 out of 10, Wonderful, (7 reviews)
"Condo was super clean!!! Amazing location! Beautiful view! We were also able to check in early which was very convenient! The absolute only thing I wild recommend it’s putting a door for the master bathroom. But we went as a couple so it wasn’t that big of a deal and we made it work! Would absolutely stay again!!"
United States
Candace
$272 nightly
The price is $278
Oct 20 - Oct 21
Total with taxes and fees
Lakeside Paradise - Waterfront, Pools, & Pickleball!
A lake with docks and boats, surrounded by buildings and greenery.

7. 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, (32 reviews)
"Excellent place for a nice little getaway!"
United States
Stephanie L.
$163 nightly
The price is $175
Oct 20 - Oct 21
Total with taxes and fees
Cozy 1-bedroom condo in charming Village of Four Seasons with WiFi, fitness room
A hotel room with a large bed, a breakfast tray with croissants, fruit, and juice, and a view of a body of water.

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

Stillwater Shores Lakefront 2bd/2BA Pool, Hot Tub 6PP
Village of Four Seasons
9.4 out of 10, Exceptional, (3 reviews)
"The stay was great. Fun bars and places to eat. The downside was the difficulty in finding the buildings address at night."
United States
leigh g.
$261 nightly
The price is $267
Oct 20 - Oct 21
Total with taxes and fees
Stillwater Shores Lakefront 2bd/2BA Pool, Hot Tub 6PP
A covered deck with a view of a lake, a dock, and a building across the water.

9. Cozy Lake Ozark Villa w/ Main Channel Views!

Cozy Lake Ozark Villa w/ Main Channel Views!
Lake Ozark
9.2 out of 10, Wonderful, (5 reviews)
"Great host Totally understanding and patient "
United States
Supreme
$154 nightly
The price is $163
Oct 20 - Oct 21
Total with taxes and fees
Cozy Lake Ozark Villa w/ Main Channel Views!
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.

10. 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, (79 reviews)
"Lovely place!"
United States
Kelly S.
$120 nightly
The price is $129
Oct 25 - Oct 26
Total with taxes and fees
Peaceful 2 bedroom Condo with NO Cleaning Fees on the Lake of the Ozarks
Dining

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

Bright & Cozy Condo with Lake, Private Balcony Views & Community Pool Retreat
Lake Ozark
10.0 out of 10, Exceptional, (2 reviews)
"Room was clean water was hot a/c was nice and cold very easy to access would stay again"
United States
Gabriel R.
$201 nightly
The price is $215
Oct 20 - Oct 21
Total with taxes and fees
Bright & Cozy Condo with Lake, Private Balcony Views & Community Pool Retreat
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.

12. 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)
"Excellent spot to stay. Was as advertised and we highly enjoyed our stay. View was also excellent from this location. 10/10 would recommend."
United States
Joel W.
$295 nightly
The price is $312
Oct 20 - Oct 21
Total with taxes and fees
3MM, fully remolded, main channel lakefront with pool
A fire pit surrounded by outdoor seating, overlooking a body of water during sunset.

13. 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
9.2 out of 10, Wonderful, (13 reviews)
"Great balcony view, great amenities, clean and quiet, perfect for my entire family. Would easily stay again!"
United States
Joseph B.
$199 nightly
The price is $204
Oct 20 - Oct 21
Total with taxes and fees
Fairway To Heaven-Four Seasons Condo 2BD/2BA/Deck/Pool/Golf/Firepit-6PP
A spacious living room with a large window overlooking a body of water, a fireplace, and a ceiling fan.

14. 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.
$315 nightly
The price is $320
Oct 22 - Oct 23
Total with taxes and fees
Emerald Oasis - Waterfront, Pools, & Smoker!
The Cave

15. Blue Cove - Pools, Hot Tub & More!

Blue Cove - Pools, Hot Tub & More!
Lake Ozark
10.0 out of 10, Exceptional, (3 reviews)
"This place was amazing. Definitely will be back"
United States
Stacy U.
$272 nightly
The price is $277
Oct 20 - Oct 21
Total with taxes and fees
Blue Cove - Pools, Hot Tub & More!
The Cave

16. Paradise Point of View

Paradise Point of View
Lake Ozark
8.6 out of 10, Excellent, (8 reviews)
"Great place to stay. "
United States
Anonymous traveler
$301 nightly
The price is $306
Oct 20 - Oct 21
Total with taxes and fees
Paradise Point of View
Outdoor dining

17. “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.
$183 nightly
The price is $196
Oct 20 - Oct 21
Total with taxes and fees
“Clabe” one of the 5 Tiny Cabins on the Osage River
The Cave

18. Heavenly Hideaway - 2 Pools, Hot Tub, & More!

Heavenly Hideaway - 2 Pools, Hot Tub, & More!
Lake Ozark
9.2 out of 10, Wonderful, (5 reviews)
"Our annual girls trip was wonderful. We had everything we needed at the place and the host was quick to answer back if we had questions. Will definitely go back."
United States
Anonymous traveler
$312 nightly
The price is $317
Oct 20 - Oct 21
Total with taxes and fees
Heavenly Hideaway - 2 Pools, Hot Tub, & More!
A stone wall, a door, and a window with a number 5 sign.

19. 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, (28 reviews)
"A perfect place for my short stay!! I will be back to stay longer next time!!"
United States
Patricia W.
$129 nightly
The price is $136
Oct 20 - Oct 21
Total with taxes and fees
Cozy 1-bedroom condo with WiFi, AC in peaceful Lake Ozark. Prime location on 4MM
The Cave

20. Top Floor Fishing Loft- Waterfront & Indoor Pool!

Top Floor Fishing Loft- Waterfront & Indoor Pool!
Village of Four Seasons
9.0 out of 10, Wonderful, (6 reviews)
"Wonderful stay. Great location and amenities. Pretty view and relaxed environment. Would definitely stay here again!"
United States
Holly L.
$262 nightly
The price is $267
Oct 20 - Oct 21
Total with taxes and fees
Top Floor Fishing Loft- Waterfront & Indoor Pool!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Olean Hotel Reviews

Capitol Plaza Hotel Jefferson City

Capitol Plaza Hotel Jefferson City

8/10 Good
"Was good everything was great"
Shadane 2-night trip
Posted 1 hour ago
Capitol Plaza Hotel Jefferson City

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 Ozark Speedway 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.