Olean Holiday Rentals

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Holiday Rentals in Olean

Remodeled Private Waterfront Cottage, Pet Friendly, with dock in Osage Beach!

10.0 out of 10, Exceptional, (227)
"The place was perfect for my son and I. Loved being able to unload the boat and leave it in the dock. Definitely plan on coming back!"
Remodeled Private Waterfront Cottage, Pet Friendly, with dock in Osage Beach!

Top-Floor Lands End Luxury Condo - Elevator - Waterpark - Pool - Wi-Fi & More!

10.0 out of 10, Exceptional, (173)
"We needed some chill time and this was the perfect condo for us at this time."
Top-Floor Lands End Luxury Condo - Elevator - Waterpark - Pool - Wi-Fi & More!

Treetop villa with panoramic view

9.8 out of 10, Exceptional, (12)
"Overall it was a nice stay, close to the water and the property was clean. It is a little dated but did not affect are stay at all. Very Satisfied"
Treetop villa with panoramic view

🦃Together for the Holidays: A Place for Thankfulness & Togetherness🍂

9.8 out of 10, Exceptional, (168)
"Connie is amazing! We needed to reschedule our dates and she got back to me in a timely manner, as well as changed our dates with no issues. This is our 2nd time staying at this house for our staff retreat and it was truly amazing. The house is absolutely beautiful and cozy. Plus great outdoor views! You definitely won't be disappointed with staying here. The only thing that I would add is to maybe put some lighting at the end of the driveway since it's a little hard to see at nighttime and a...
The price is AU$2,248
includes taxes & fees
1 Dec - 2 Dec
🦃Together for the Holidays: A Place for Thankfulness & Togetherness🍂

Lake Life: Amazing Weekday Specials! Dock, Swim Mat, Cove Water

9.8 out of 10, Exceptional, (9)
"This house was clean and great as far as size for a large group, what was provided in the home and had a nice view of a quiet location on the lake. The only issues we had were the garbage was never picked up all week even after notifying the property manager and the road to get in and out was treacherous which was not mentioned in the listing. "
Lake Life: Amazing Weekday Specials! Dock, Swim Mat, Cove Water

SALE!-2bd/2bth,waterfront,amazing pool on point,hot tub,gated community

9.6 out of 10, Exceptional, (148)
"Property as advertised, great location, great pool."
SALE!-2bd/2bth,waterfront,amazing pool on point,hot tub,gated community

UNIT 75 - TREELOFT 3 BEDROOM VILLA

UNIT 75 - TREELOFT 3 BEDROOM VILLA

Sleeps 10, large deep water dock, 2 swim platforms- ladders & covered slip.

9.8 out of 10, Exceptional, (29)
"Loved this beautiful home and all its coziness, we would definitely stay again. "
Sleeps 10, large deep water dock, 2 swim platforms- ladders & covered slip.

Amazing Lake Experiences! Private Hot Tub, Aamazing Dock, Firepit & Two Layers of Decks

10.0 out of 10, Exceptional, (22)
"Easy access to the dock and lake. Loved the kayaks and pedal boat. Kids and grandkids spent most of their time on the lily pad, swimming, diving platform, fishing. Thank you for an enjoyable weekend."
Amazing Lake Experiences! Private Hot Tub, Aamazing Dock, Firepit & Two Layers of Decks

Porto Cima Exclusive Luxury Mansion! Private Pool! Master Spa Hot Tub! Game Room

9.4 out of 10, Exceptional, (59)
"We celebrated our anniversary with our five children, their spouses, eighteen grandchildren, ages 2 to 24, and one great grandchild. We did not feel crowded at all. The kitchen was wonderful and had a nice pantry attached. The garage which was converted into a game room was popular with everyone. We all appreciated the fact that so many of the bedrooms were king suites. Communication with the property host, John, was excellent. This is a beautiful and spacious home and the views from their...
Porto Cima Exclusive Luxury Mansion! Private Pool! Master Spa Hot Tub! Game Room

Best Cove & Private! Hot Tub! Large Dock! Jumping board! Near Strip! Pool near!

9.8 out of 10, Exceptional, (84)
"We had an amazing time and this place was perfect for our needs! The location was beautiful and easy to get to, and the place had everything we could need. The girls are already making plans to come back next year! Thanks for everything. "
The price is AU$618
includes taxes & fees
3 Dec - 4 Dec
Best Cove & Private! Hot Tub! Large Dock! Jumping board! Near Strip! Pool near!

Amazing Wall of Windows, Swim Dock & Pet Friendly

9.4 out of 10, Exceptional, (12)
"Dog day "
Amazing Wall of Windows, Swim Dock & Pet Friendly

Luxurious, 5 Star Experience, Lakefront Home on Horseshoe Bend

10.0 out of 10, Exceptional, (239)
"This was an amazing lake house, the hosts were very helpful and friendly. Great views, very relaxing, the house had everything you would need or want. This was my first visit to Lake of Ozarks.it won't be my lastit won't be my lasr. "
Luxurious, 5 Star Experience, Lakefront Home on Horseshoe Bend

Magazine-Featured Mansion, Golf Green, Casino, etc

9.8 out of 10, Exceptional, (12)
"We would come back to this awesome lake house at any future vacation time it was an excellent place it filled all expectations "
The price is AU$1,388
includes taxes & fees
2 Dec - 3 Dec
Magazine-Featured Mansion, Golf Green, Casino, etc

Private Pool, Dock, Lots of Deck Space, Amazing Views, Quiet Location, Lots of Space

9.2 out of 10, Wonderful, (36)
"Had the best time! "
Private Pool, Dock, Lots of Deck Space, Amazing Views, Quiet Location, Lots of Space

Lakefront Condo,2BR/2BA, Indoor & Outdoor pool/Hot Tub, WIFI,Tennis, Basketball

9.4 out of 10, Exceptional, (176)
"We have stayed in this condo before. We like this location in the ozarks. We enjoyed sitting on the deck with a wonderful view of the water and boats. The ducks and turtles can be entertaining. Even though there is alot of stairs this is a favorite condo in southwood shores. The owners are very nice and helpful. We will be returning next fall "
Lakefront Condo,2BR/2BA, Indoor & Outdoor pool/Hot Tub, WIFI,Tennis, Basketball

LOCATION, LOCATION, AND LOCATION!

10.0 out of 10, Exceptional, (97)
"Love the place great location "
The price is AU$336
includes taxes & fees
1 Dec - 2 Dec
LOCATION, LOCATION, AND LOCATION!

Right on the Water w/ Own Dock, Pet Friendly Flat Lot, Wheel Chair accessible!

9.8 out of 10, Exceptional, (102)
"The house is very spacious and comfortable. We had a great 3 day weekend ! The beds were all very comfortable and the layout worked well for our family. There were 2 adults, 4 teenagers and our dog. Plenty of room for us all! Great cove for swimming or using the Lilly pad. I would give this house and location a 10/10"
Right on the Water w/ Own Dock, Pet Friendly Flat Lot, Wheel Chair accessible!

Lake Of The Ozarks ~ Great Family Rental With The Best View On The Lake!

9.8 out of 10, Exceptional, (113)
"This place was perfect for our family of 8 adults and a 10 month old baby. The separate rooms and two levels were great. It was stocked with everything you would need. Except food. You could cook anything you wanted, the kitchen had every pot or pan, every utensil. It was very clean. The outdoor space is very big with chairs and tables everywhere, the private swim dock was spacious and a fun spot. Everyone loved it and said they wanted to come back next year A+ "
Lake Of The Ozarks ~ Great Family Rental With The Best View On The Lake!

Great lake front Location-Gorgeous View- a Lake House Getaway Near Laurie

9.6 out of 10, Exceptional, (98)
"We had an amazing weekend with great friends. The house has everything you need and the view of the lake is spectacular. "
Great lake front Location-Gorgeous View- a Lake House Getaway Near Laurie
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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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, (1132)
"It was nice back in the day...Its an older hotel...could use updates...or make it all Rustic...lodge style..."
The price is AU$161
includes taxes & fees
30 Nov - 1 Dec
Lodge Of Four Seasons Golf Resort, Marina & Spa

The Resort at Lake of the Ozarks

3.0 star property
8.2 out of 10, Very good, (338)
"Nice close to everything and has a bar area where bands play...theyll even give u a golf cart ride back to your hotel..."
The price is AU$165
includes taxes & fees
30 Nov - 1 Dec
The Resort at Lake of the Ozarks

Capitol Plaza Hotel Jefferson City

3.5 star property
7.0 out of 10, Good, (1116)
"Close to capital building "
The price is AU$179
includes taxes & fees
1 Dec - 2 Dec
Capitol Plaza Hotel 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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

🦃Together for the Holidays: A Place for Thankfulness & Togetherness🍂: 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.