Holiday Rentals in Olean

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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, (31 reviews)
"Perfect place to stay for my trip"
United States
Joshua B.
The price is €146
includes taxes & fees
26 Apr - 27 Apr
Business or Pleasure - a perfect and cozy get-away!

The Carriage House at Parker's Place

The Carriage House at Parker's Place
Jefferson City
10.0 out of 10, Exceptional, (49 reviews)
"Excellent stay! Charming house. Great location. Perfect for an extended stay."
United States
Ellen R.
The price is €247
includes taxes & fees
19 Apr - 20 Apr
The Carriage House at Parker's Place

2BD, 1BA Home. 5-10 Minutes to ANYWHERE in JCMO!

2BD, 1BA Home. 5-10 Minutes to ANYWHERE in JCMO!
Jefferson City
10.0 out of 10, Exceptional, (40 reviews)
"It was a great stay!! Lovely place. "
United States
Heidi L.
The price is €198
includes taxes & fees
3 May - 4 May
2BD, 1BA Home. 5-10 Minutes to ANYWHERE in JCMO!

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
The price is €140
includes taxes & fees
22 Apr - 23 Apr
Charming cabin with WiFi and AC in delightful Eldon

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
The price is €150
includes taxes & fees
19 Apr - 20 Apr
Pinkies Paradise-3BD/2BA/Sleeps 8PP-Lake Ozark

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
The price is €407
includes taxes & fees
19 Apr - 20 Apr
Historic 4-bedroom pet friendly rental close to downtown.

Lakefront Stargazer - Fireplace - Desk - King & Queen Beds - Stunning Views

Lakefront Stargazer - Fireplace - Desk - King & Queen Beds - Stunning Views
Osage Beach
10.0 out of 10, Exceptional, (30 reviews)
"Clean and comfortable place to stay while working in Osage Beach. "
United States
Johnna S.
The price is €224
includes taxes & fees
30 Apr - 1 May
Lakefront Stargazer - Fireplace - Desk - King & Queen Beds - Stunning Views

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

Beach Cabin #6, Private/Shared Beach - Cabin #6
Lake Ozark
The price is €223
includes taxes & fees
19 Apr - 20 Apr
Beach Cabin #6, Private/Shared Beach - Cabin #6

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

Cedar Sanctuary #17-2BD/2BA/Pools/Grill/Dock/Firepit-4PP
Village of Four Seasons
10.0 out of 10, Exceptional, (2 reviews)
"Everything was great!"
United States
Jeffrey B.
The price is €226
includes taxes & fees
21 Apr - 22 Apr
Cedar Sanctuary #17-2BD/2BA/Pools/Grill/Dock/Firepit-4PP

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, (34 reviews)
"The house was conveniently located near the train station and the Capital! It was very clean and had lots of fun games!"
United States
Mary H.
The price is €285
includes taxes & fees
29 Apr - 30 Apr
The Big House, Historic 4-Bedroom Home With Custom Art And Dedicated Workspace

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.
The price is €134
includes taxes & fees
19 May - 20 May
Lake of the Ozarks North Shore Cabin on the quiet side of lake.

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.
The price is €236
includes taxes & fees
20 Apr - 21 Apr
Turtle Cove – Lakefront & Indoor Pool!

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, (13 reviews)
"The place was nice and the host was helpful. "
United States
Nathan R.
The price is €152
includes taxes & fees
26 Apr - 27 Apr
Cozy 1-bedroom condo in charming Village of Four Seasons with WiFi, fitness room

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

SALE! Lakefront | 4 Pools | Dock | Sauna | +Resort
Lake Ozark
9.4 out of 10, Exceptional, (13 reviews)
"I will definitely stay there again. The home was beautiful. "
United States
Megan L.
The price is €376
includes taxes & fees
20 Apr - 21 Apr
SALE! Lakefront | 4 Pools | Dock | Sauna | +Resort

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.
Sunset Spectacular – Waterfront & Indoor Pool!

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

Treetop VIllage Four Seasons #10-Lakefront/2BD/3BA/Pools/Grill/Dock/Firepit-4PP
Village of Four Seasons
8.4 out of 10, Very good, (5 reviews)
"Communication was a little difficulty at times but overall we loved our time here!"
United States
Kelley H.
The price is €206
includes taxes & fees
26 Apr - 27 Apr
Treetop VIllage Four Seasons #10-Lakefront/2BD/3BA/Pools/Grill/Dock/Firepit-4PP

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.
The price is €241
includes taxes & fees
19 Apr - 20 Apr
Summer Serenity Waterfront Condo!- Indoor Pool!

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

Hideaway in the Trees-#30-Lakefront/2BD/3BA/Pools/Grill/Dock/Firepit-4PP
Village of Four Seasons
9.6 out of 10, Exceptional, (7 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.
The price is €255
includes taxes & fees
23 Apr - 24 Apr
Hideaway in the Trees-#30-Lakefront/2BD/3BA/Pools/Grill/Dock/Firepit-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
The price is €236
includes taxes & fees
19 Apr - 20 Apr
Lakeside Paradise - Waterfront, Pools, & Pickleball!

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, (81 reviews)
"Great place!"
United States
J.D. L.
The price is €263
includes taxes & fees
25 Apr - 26 Apr
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 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, apart-hotels, 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 €152 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?

Porto Cima - Amazing 6,500 SF Home - Private Heated Pool, Arcade, Sleeps 30 PLUS: This holiday home rental outside of Olean is located on a lake, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 Course.

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.