Olean Holiday Rentals

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Our top choices for Olean holiday 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, (29)
"Perfect place to stay for my trip"
United States
Joshua B.
The price is NZ$281
includes taxes & fees
19 Jan - 20 Jan
Business or Pleasure - a perfect and cozy get-away!

Historic 4-bedroom pet friendly rental close to downtown.

Historic 4-bedroom pet friendly rental close to downtown.
2.0 star property
Jefferson City
The price is NZ$494
includes taxes & fees
9 Jan - 10 Jan
Historic 4-bedroom pet friendly rental close to downtown.

The Carriage House at Parker's Place

The Carriage House at Parker's Place
Jefferson City
10.0 out of 10, Exceptional, (46)
"Perfect location and very comfortable place. "
United States
Holly B.
The price is NZ$466
includes taxes & fees
11 Jan - 12 Jan
The Carriage House at Parker's Place

“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, (2)
"It was a great quiet place to get away for a weekend."
United States
Kyle B.
The price is NZ$304
includes taxes & fees
9 Jan - 10 Jan
“Clabe” one of the 5 Tiny Cabins on the Osage River

A Home Away From Home

A Home Away From Home
2.0 star property
Jefferson City
7.6 out of 10, Good, (4)
"Very spacious, clean, and easily accessible"
United States
Briana
The price is NZ$303
includes taxes & fees
30 Jan - 31 Jan
A Home Away From Home

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
10.0 out of 10, Exceptional, (8)
"Condo was just as expected and in a great location!"
United States
Ashley R.
The price is NZ$287
includes taxes & fees
9 Jan - 10 Jan
Cozy 1-bedroom condo in charming Village of Four Seasons with WiFi, fitness room

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, (12)
"Very happy with our stay, and the great communication with our host. "
United States
Greg K.
The price is NZ$192
includes taxes & fees
9 Jan - 10 Jan
Cozy 1-bedroom condo with WiFi, AC in peaceful Lake Ozark. Prime location on 4MM

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
2.0 star property
Jefferson City
10.0 out of 10, Exceptional, (30)
"Very clean and well appointed. Nice location."
United States
Thomas C.
The price is NZ$505
includes taxes & fees
19 Jan - 20 Jan
The Big House, Historic 4-Bedroom Home With Custom Art And Dedicated Workspace

Charming cabin with WiFi and AC in delightful Eldon

Charming cabin with WiFi and AC in delightful Eldon
Eldon
9.2 out of 10, Wonderful, (9)
"Wonderful cabin. Absolutely recommend!!"
United States
Vivian
The price is NZ$278
includes taxes & fees
15 Jan - 16 Jan
Charming cabin with WiFi and AC in delightful Eldon

Turtle Cove – Lakefront & Indoor Pool!

Turtle Cove – Lakefront & Indoor Pool!
Village of Four Seasons
9.6 out of 10, Exceptional, (7)
"We had a wonderful relaxing stay. The condo was perfect."
United States
Kasie W.
The price is NZ$476
includes taxes & fees
11 Jan - 12 Jan
Turtle Cove – Lakefront & Indoor Pool!

Sunset Spectacular – Waterfront & Indoor Pool!

Sunset Spectacular – Waterfront & Indoor Pool!
Village of Four Seasons
10.0 out of 10, Exceptional, (5)
"The unit was spacious. The area was great. The pool was nice as well and stayed open until midnight! "
United States
Josh W.
The price is NZ$486
includes taxes & fees
3 Feb - 4 Feb
Sunset Spectacular – Waterfront & Indoor Pool!

Lakeside Paradise - Waterfront, Pools, & Pickleball!

Lakeside Paradise - Waterfront, Pools, & Pickleball!
Lake Ozark
9.6 out of 10, Exceptional, (5)
"This condo was amazing!!! Had everything we needed, would highly recommend!!"
United States
Kathryn H.
The price is NZ$476
includes taxes & fees
11 Jan - 12 Jan
Lakeside Paradise - Waterfront, Pools, & Pickleball!

Waterfront Cozy Cove Retreat - LOTO Escape, Remodeled Comfort, Close to the Fun

Waterfront Cozy Cove Retreat - LOTO Escape, Remodeled Comfort, Close to the Fun
2.5 star property
Lake Ozark
10.0 out of 10, Exceptional, (3)
"If you're looking for a great place to call home on your trip - this is the place to do it! Rachel's place was better than described and we were even greeted with snacks and champagne for Mimosas. The place was spotless and very well stocked with about anything you would need for your stay. As for your host "Rachel" she went above and beyond, and you'll have a hard time finding a better one. Communication was absolutely seamless. "
United States
Joseph P.
The price is NZ$490
includes taxes & fees
9 Jan - 10 Jan
Waterfront Cozy Cove Retreat - LOTO Escape, Remodeled Comfort, Close to the Fun

Top Floor 2Bd 2Bath Condo at Lighthouse Landing!

Top Floor 2Bd 2Bath Condo at Lighthouse Landing!
2.0 star property
Lake Ozark
9.4 out of 10, Exceptional, (6)
"Excellent accommodations and check-in and check-out were a breeze. Very pleased with entire trip. "
United States
Nick A.
The price is NZ$584
includes taxes & fees
11 Jan - 12 Jan
Top Floor 2Bd 2Bath Condo at Lighthouse Landing!

SALE! New Treetop, 2 pools, dock, hot tub!

SALE! New Treetop, 2 pools, dock, hot tub!
2.0 star property
Lake Ozark
9.2 out of 10, Wonderful, (9)
"I will definitely stay there again. The home was beautiful. "
United States
Megan L.
The price is NZ$785
includes taxes & fees
11 Jan - 12 Jan
SALE! New Treetop, 2 pools, dock, hot tub!

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, (2)
"Great stay! Would definitely come back!"
United States
Mikeshei K.
The price is NZ$260
includes taxes & fees
29 Jan - 30 Jan
Lake of the Ozarks North Shore Cabin on the quiet side of lake.

The Sunrise Suite – Waterfront Screened Balcony w/Pool!

The Sunrise Suite – Waterfront Screened Balcony w/Pool!
Lake Ozark
9.8 out of 10, Exceptional, (8)
"This condo was absolutely amazing it had everything you could need and more ! It was the perfect getaway for my children and I ! "
United States
Amanda M.
The price is NZ$466
includes taxes & fees
11 Jan - 12 Jan
The Sunrise Suite – Waterfront Screened Balcony w/Pool!

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)
"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.
The price is NZ$281
includes taxes & fees
16 Jan - 17 Jan
Water facing Condo on Horseshoe bend mins from the Strip avail PWC 12 X 28 Slips

Emerald Oasis - Waterfront, Pools, & Smoker!

Emerald Oasis - Waterfront, Pools, & Smoker!
Lake Ozark
10.0 out of 10, Exceptional, (6)
"Lovely property, Unit, & Location. Would stay again"
United States
Steven W.
The price is NZ$520
includes taxes & fees
11 Jan - 12 Jan
Emerald Oasis - Waterfront, Pools, & Smoker!

Hideaway at Harbour Towne

Hideaway at Harbour Towne
2.5 star property
Lake Ozark
10.0 out of 10, Exceptional, (10)
"It was perfect for our girls getaway! "
United States
Cindy S.
The price is NZ$645
includes taxes & fees
11 Jan - 12 Jan
Hideaway at Harbour Towne
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Olean holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Olean holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Olean holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Olean holiday rentals we have selected for you start as low as NZ$513 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Olean rentals

At Expedia, we put the best Olean holiday 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 holiday.

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 holiday rentals in Olean?

Yes, there are holiday rentals close to the most popular sights in Olean, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Olean has to offer?

Pet-Friendly Home In The Main Channel w/ Breathtaking Sunsets & Lake Views: This holiday home rental outside of Olean is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

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 wider area, you’ll find Lake Ozark Speedway and Osage National Golf Club.

What’s a holiday rental in Olean like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Olean. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for a family trip or a small group gathering.