Olean Holiday Rentals

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Holiday Rentals in Olean

2 BEDROOM NAUTICAL CONDO OVERLOOKING LAKE NEXT TO BAGNELL STRIP
10.0 out of 10, Exceptional, (24)
"Great cabin and nice accommodations."
2 BEDROOM NAUTICAL CONDO OVERLOOKING LAKE NEXT TO BAGNELL STRIP
3MM, fully remolded, main channel lakefront with pool
10.0 out of 10, Exceptional, (31)
"visited this lovely property with a group of friends and it was the perfect location for a relaxing weekend!"
The price is AU$459
per night
17 June - 18 June
3MM, fully remolded, main channel lakefront with pool
Tree Top 16 a unique Lake vacation experience!
9.4 out of 10, Exceptional, (94)
"Everything was perfect and beat expectations. The house was cozy, and the 360 lake views (through an all glass wall design) was serene. The kitchen is compact but was well equipped; it was able to handle needs for a short stay. Both bed rooms are good size and good for kids or adults. All in all perfect for a family getaway - one you can enjoy all four seasons."
Tree Top 16 a unique Lake vacation experience!
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Retreats, Families, Friends, STUNNING & SECLUDED; Quiet Cove close to all!!!
9.8 out of 10, Exceptional, (154)
"Beautiful house, secluded lot, quiet cove, close to shopping/restaurants. The house was amazing! Clean beautiful decor, plenty of space, great attention to detail ❤️ definitely would come back!"
The price is AU$2,717
per night
15 June - 16 June
Retreats, Families, Friends, STUNNING & SECLUDED; Quiet Cove close to all!!!
1st-floor condo with incl. boat slip & lake-view deck + on-site pools & hot tub
9.0 out of 10, Wonderful, (8)
"It was nice a quite property, the bed was hard and couldnt get it to heat up inside at all froze all night even using the extra blankets. Im sure the coolness will be great for the summer. Had a hard time getting in the gate as well wasnt given the right gate code for arrival"
The price is AU$539
per night
16 June - 17 June
1st-floor condo with incl. boat slip & lake-view deck + on-site pools & hot tub
😍FANTASIC NEWS! NO STAIRS Level 300' of frontage, Pretty incredible, right?
9.8 out of 10, Exceptional, (152)
"Both the house and the dock were amazing"
The price is AU$1,625
per night
4 June - 5 June
😍FANTASIC NEWS! NO STAIRS Level 300' of frontage, Pretty incredible, right?
NEW LISTING! Cozy Lakefront Home with fantastic views, close to Bagnell Dam
9.6 out of 10, Exceptional, (42)
"Great view of the lake and short drive to the strip. House had everything we needed. Perfect for 3 couples."
NEW LISTING! Cozy Lakefront Home with fantastic views, close to Bagnell Dam
UNIT 75 - TREELOFT 3 BEDROOM VILLA
UNIT 75 - TREELOFT 3 BEDROOM VILLA
Treetop villa with panoramic view
9.6 out of 10, Exceptional, (9)
"We (4 couples) loved this house! We instantly felt right at home with everything at our fingertips. The kitchen is perfectly stocked, there's plenty of room for everyone to do their thing. Large dining table, room for everyone to be in the kitchen, large room downstairs for those watching TV, playing games... Bedrooms were very comfortable with great views. John and his group were so responsive when we had a question or request. We highly recommend this great house!"
Treetop villa with panoramic view
Lake of the Ozarks Vacation Rental: Boat Dock/Slip
10.0 out of 10, Exceptional, (3)
"Loved the place. Beds comfortable. Dock very nice."
Lake of the Ozarks Vacation Rental: Boat Dock/Slip
Cozy lake in front of the home
9.6 out of 10, Exceptional, (82)
"Quiet, peaceful with a stunning view. We will be back."
Cozy lake in front of the home
Charming condo on the 4 mile marker of the lake of the ozarks.
9.2 out of 10, Wonderful, (12)
"Peaceful and cozy! Will definitely stay again."
Charming condo on the 4 mile marker of the lake of the ozarks.
Gentle slope to Lakefront, FAMILY & FRIENDS Lake Time MEMORIES!!
9.6 out of 10, Exceptional, (144)
"We stay in vacation homes at LOZ several times throughout the summer and this home was the best one yet! It was clean, roomy, and had everything we needed to have a perfect holiday weekend. The house had tons of parking and was located in a nice calm cove. The dock was amazing and provided us with hours of fun. At night we enjoyed playing fun games at the huge kitchen table that accommodated us all. We will definitely come back to this home again because everything about it was perfect!"
The price is AU$1,473
per night
10 June - 11 June
Gentle slope to Lakefront, FAMILY & FRIENDS Lake Time MEMORIES!!
Million dollar view-Horseshoe Bend
10.0 out of 10, Exceptional, (30)
"You can go wrong with this vacation stay. Everything was as described and actually even nicer once arrived. the views were great and you can beat the location on Horseshoe bend. Just minutes away from almost everything you could possibly need/want. 10/10 would stay again and recommend this for whoever may be reading."
Million dollar view-Horseshoe Bend
Heart of Osage Beach w the Best view of the lake down the main channel 4 miles
10.0 out of 10, Exceptional, (6)
"The Portal is a wonderful condo that was better than expected. It’s cute and unique and close to everything. While we were in Osage Beach for a baseball tournament, the condo provided us a retreat to relax as a family."
The price is AU$280
per night
5 June - 6 June
Heart of Osage Beach w the Best view of the lake down the main channel 4 miles
Waterfront Osage Beach Condo w/ Patio & Grill
9.4 out of 10, Exceptional, (13)
"I wonderful condo with great amenities and close to everything!"
Waterfront Osage Beach Condo w/ Patio & Grill
Buddy's Harbor
2.5 star property
9.2 out of 10, Wonderful, (35)
"I love the location of this property I have been coming here for 8 years with my family every year multiple times BUT the owners have changed and the new owners are controlling and follow you around, (The woman specifically) We had a friend come over for a birthday party and he was handicapped and the owner said I hope you blow yourself up because he was standing by the grill and she got in his face and asked him who are you here with not knowing he was handicapped she screamed in his face ( ive...
Buddy's Harbor
LOCATION, LOCATION, AND LOCATION!
9.8 out of 10, Exceptional, (80)
"The condo met our (2 couples) needs well with two bedrooms, each with an attached bath. The kitchen was well stocked, although we did not really use it except to make coffee. Our only complaint was the pitiful little bath towels in the bathrooms. Each only had 2, small raggedy towels. On the next to last day, we found a load of much nicer towels in the dryer. It would have been nice if the cleaners had put them in the bathrooms."
LOCATION, LOCATION, AND LOCATION!
Waterfront Condo, 2 Bed, 2.5 Bath, Sleeps 6
10.0 out of 10, Exceptional, (20)
"This is a great spot if you have a boat and like to fish. Slip is conveniently located. Its an easy walk from the first level condo to the boat slip. Great Four Seasons location close to many amenities. Would highly recommend."
Waterfront Condo, 2 Bed, 2.5 Bath, Sleeps 6
Lakefront Condo,2BR/2BA, Indoor & Outdoor pool/Hot Tub, WIFI,Tennis, Basketball
9.4 out of 10, Exceptional, (162)
"The overwhelming thing that should be pointed out is there are 30 steps. Two females had a difficult time navigating with luggage and groceries. If you’re young and healthy, great. The toilets had black mold and the screen door is completely broken. The wrong gate code was given to us so that took some time. The good: Location is great, complex seemed safe, it’s literally RIGHT on the dock/water and is decorated really cute."
The price is AU$654
per night
3 July - 4 July
Lakefront Condo,2BR/2BA, Indoor & Outdoor pool/Hot Tub, WIFI,Tennis, Basketball
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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.

Other types of properties in Olean you may be interested in

Lodge Of Four Seasons Golf Resort, Marina & Spa
4.0 star property
7.4 out of 10, Good, (1012)
"Needs to be updated "
The price is AU$309
per night
4 June - 5 June
Lodge Of Four Seasons Golf Resort, Marina & Spa
The Resort at Lake of the Ozarks
3.0 star property
8.4 out of 10, Very good, (116)
"Amazing stay in the Ozarks right next to Encore. A beautiful restaurant and pool bar overlooking the lake and a very nice poolside bar. The room was spacious and clean. Absolutely would love to go back"
The price is AU$271
per night
9 June - 10 June
The Resort at Lake of the Ozarks
Baymont by Wyndham Jefferson City
2.5 star property
8.2 out of 10, Very good, (1005)
"Everything was perfect "
The price is AU$138
per night
23 June - 24 June
Baymont by Wyndham Jefferson City
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.

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 favourite 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 depend 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 AU$280 per night. Entering your travel dates in the search wizard might find you 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?

💕Retreats, Families, Friends, STUNNING & SECLUDED Voted #1 by USA Today!: 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 8 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 garden, 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 Horseshoebend. In the wider area, you’ll find Osage National Golf Club 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.

Recent reviews of Olean properties
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