Olean Holiday Rentals

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Our top choices for Olean holiday rentals

The Carriage House at Parker's Place

The Carriage House at Parker's Place
Jefferson City
10.0 out of 10, Exceptional, (48 reviews)
"Excellent stay! Charming house. Great location. Perfect for an extended stay."
United States
Ellen R.
The price is NZ$535
includes taxes & fees
19 Apr - 20 Apr
The Carriage House at Parker's Place

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 NZ$286
includes taxes & fees
15 Apr - 16 Apr
Business or Pleasure - a perfect and cozy get-away!

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 NZ$390
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 NZ$273
includes taxes & fees
14 Apr - 15 Apr
Charming cabin with WiFi and AC in delightful Eldon

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

Beach Cabin #6, Private/Shared Beach - Cabin #6
Lake Ozark
The price is NZ$403
includes taxes & fees
14 Apr - 15 Apr
Beach Cabin #6, Private/Shared Beach - Cabin #6

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 NZ$820
includes taxes & fees
16 Apr - 17 Apr
Historic 4-bedroom pet friendly rental close to downtown.

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 NZ$299
includes taxes & fees
19 Apr - 20 Apr
Cozy 1-bedroom condo in charming Village of Four Seasons with WiFi, fitness room

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 NZ$561
includes taxes & fees
6 May - 7 May
The Big House, Historic 4-Bedroom Home With Custom Art And Dedicated Workspace

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 NZ$521
includes taxes & fees
14 Apr - 15 Apr
Newly remodeled updated condo,12x32 Boat slip, wi-Fi Internet cable TV, pwc slip

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 NZ$751
includes taxes & fees
14 Apr - 15 Apr
SALE! Lakefront | 4 Pools | Dock | Sauna | +Resort

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 NZ$407
includes taxes & fees
14 Apr - 15 Apr
Treetop VIllage Four Seasons #10-Lakefront/2BD/3BA/Pools/Grill/Dock/Firepit-4PP

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 NZ$262
includes taxes & fees
14 Apr - 15 Apr
Lake of the Ozarks North Shore Cabin on the quiet side of lake.

Stylish Lakefront, King Bed Suite, Sunset View, Pool, Boat Slip, PrivateTopFloor

Stylish Lakefront, King Bed Suite, Sunset View, Pool, Boat Slip, PrivateTopFloor
Osage Beach
10.0 out of 10, Exceptional, (94 reviews)
"She was great wonderful suggestions we love the view close to mamy places to enjoy "
United States
Jeannie B.
The price is NZ$438
includes taxes & fees
20 Apr - 21 Apr
Stylish Lakefront, King Bed Suite, Sunset View, Pool, Boat Slip, PrivateTopFloor

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 NZ$445
includes taxes & fees
14 Apr - 15 Apr
Cedar Sanctuary #17-2BD/2BA/Pools/Grill/Dock/Firepit-4PP

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
8.8 out of 10, Excellent, (10 reviews)
"Great balcony view, great amenities, clean and quiet, perfect for my entire family. Would easily stay again!"
United States
Joseph B.
The price is NZ$842
includes taxes & fees
14 Apr - 15 Apr
Fairway To Heaven-Four Seasons Condo 2BD/2BA/Deck/Pool/Golf/Firepit-6PP

Walk to The Strip! Great Cove Water for Lake Fun

Walk to The Strip! Great Cove Water for Lake Fun
Lake Ozark
9.8 out of 10, Exceptional, (20 reviews)
"A wonderful home with gorgeous lake views. Very peaceful, and overall the perfect little place to relax! "
United States
Kathryn M.
The price is NZ$537
includes taxes & fees
20 Apr - 21 Apr
Walk to The Strip! Great Cove Water for Lake Fun

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 NZ$481
includes taxes & fees
14 Apr - 15 Apr
Summer Serenity Waterfront Condo!- Indoor Pool!

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 NZ$468
includes taxes & fees
20 Apr - 21 Apr
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 reviews)
"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$471
includes taxes & fees
14 Apr - 15 Apr
Sunset Spectacular – Waterfront & 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 NZ$500
includes taxes & fees
16 Apr - 17 Apr
Hideaway in the Trees-#30-Lakefront/2BD/3BA/Pools/Grill/Dock/Firepit-4PP
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$299 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 Osage National Golf Course and Lake of the Ozarks and Bagnell Dam Viewpoint.

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.