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 AU$410
includes taxes & fees
12 Apr - 13 Apr
The Carriage House at Parker's Place

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 AU$229
includes taxes & fees
13 Apr - 14 Apr
Charming cabin with WiFi and AC in delightful Eldon

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 AU$680
includes taxes & fees
12 Apr - 13 Apr
Historic 4-bedroom pet friendly rental close to downtown.

Powell Lakehouse | Hot Tub, Dock & Sunset Views | Featured on Staycation episode

Powell Lakehouse | Hot Tub, Dock & Sunset Views | Featured on Staycation episode
Sunrise Beach
10.0 out of 10, Exceptional, (103 reviews)
"Very nice property that housed our family for a great weekend on the lake. Nice to have a dock to put our boat close by while not on the water. Host were very kind and accommodating. Definitely recommend this property. "
United States
nathan
The price is AU$650
includes taxes & fees
10 Apr - 11 Apr
Powell Lakehouse | Hot Tub, Dock & Sunset Views | Featured on Staycation episode

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 AU$442
includes taxes & fees
9 Apr - 10 Apr
Newly remodeled updated condo,12x32 Boat slip, wi-Fi Internet cable TV, pwc slip

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, (93 reviews)
"Great place to stay with great view. Property managers were great and easy to contact, and quick to respond to us with a question we had. I would stay here again"
United States
Marcus B.
The price is AU$352
includes taxes & fees
20 Apr - 21 Apr
Stylish Lakefront, King Bed Suite, Sunset View, Pool, Boat Slip, PrivateTopFloor

Stunning Views, Inviting Pools, and Endless Fun!

Stunning Views, Inviting Pools, and Endless Fun!
Osage Beach
9.8 out of 10, Exceptional, (12 reviews)
"Super cute place and a great location, perfect for our girls getaway! "
United States
Stacey M.
The price is AU$828
includes taxes & fees
9 Apr - 10 Apr
Stunning Views, Inviting Pools, and Endless Fun!

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

SALE! Lakefront | 4 Pools | Dock | Sauna | +Resort
Lake Ozark
9.4 out of 10, Exceptional, (12 reviews)
"I will definitely stay there again. The home was beautiful. "
United States
Megan L.
The price is AU$617
includes taxes & fees
13 Apr - 14 Apr
SALE! Lakefront | 4 Pools | Dock | Sauna | +Resort

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 AU$711
includes taxes & fees
9 Apr - 10 Apr
Fairway To Heaven-Four Seasons Condo 2BD/2BA/Deck/Pool/Golf/Firepit-6PP

Regatta Bay Getaway-Luxury Lakefront Condo/2BD/2BA/Deck/Pool/Dock-6PP

Regatta Bay Getaway-Luxury Lakefront Condo/2BD/2BA/Deck/Pool/Dock-6PP
Lake Ozark
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful condo, great location on the lake. Would stay again in a heartbeat"
United States
Nick C.
The price is AU$445
includes taxes & fees
9 Apr - 10 Apr
Regatta Bay Getaway-Luxury Lakefront Condo/2BD/2BA/Deck/Pool/Dock-6PP

Lakefront cozy cottage!

Lakefront cozy cottage!
Rocky Mount
9.8 out of 10, Exceptional, (11 reviews)
"Comfortable stay, great fishing and kids loved swimming off the dock! "
United States
Jessica H.
The price is AU$443
includes taxes & fees
9 Apr - 10 Apr
Lakefront cozy cottage!

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 AU$251
includes taxes & fees
11 Apr - 12 Apr
Cozy 1-bedroom condo in charming Village of Four Seasons with WiFi, fitness room

Treetop Vibes on Horseshoe Bend

Treetop Vibes on Horseshoe Bend
Lake Ozark
9.2 out of 10, Wonderful, (11 reviews)
"Great time, beautiful property, everything was perfect! Will definitely be back. "
United States
Lydia B.
The price is AU$480
includes taxes & fees
13 Apr - 14 Apr
Treetop Vibes on Horseshoe Bend

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 AU$240
includes taxes & fees
13 Apr - 14 Apr
Business or Pleasure - a perfect and cozy get-away!

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, (17 reviews)
"Very happy with our stay, and the great communication with our host. "
United States
Greg K.
The price is AU$242
includes taxes & fees
17 Apr - 18 Apr
Cozy 1-bedroom condo with WiFi, AC in peaceful Lake Ozark. Prime location on 4MM

Our Cove Retreat - Perfect for Wave-Free Swimming, Tanning & Prime Location Fun!

Our Cove Retreat - Perfect for Wave-Free Swimming, Tanning & Prime Location Fun!
Lake Ozark
9.8 out of 10, Exceptional, (25 reviews)
"Great place!"
United States
Amber M.
The price is AU$430
includes taxes & fees
9 Apr - 10 Apr
Our Cove Retreat - Perfect for Wave-Free Swimming, Tanning & Prime Location Fun!

Penthouse Level Condo w/ Lake & Pool Views, Tennis & Pickleball

Penthouse Level Condo w/ Lake & Pool Views, Tennis & Pickleball
Lake Ozark
10.0 out of 10, Exceptional, (8 reviews)
"One of the cleanest rentals I stayed in. "
United States
Jeff D.
The price is AU$649
includes taxes & fees
9 Apr - 10 Apr
Penthouse Level Condo w/ Lake & Pool Views, Tennis & Pickleball

Amazing Lakefront Pool On Coveted Horseshoe Bend!

Amazing Lakefront Pool On Coveted Horseshoe Bend!
Four Seasons
9.2 out of 10, Wonderful, (12 reviews)
"Beautiful Property, great location!"
United States
Allan M.
The price is AU$432
includes taxes & fees
9 Apr - 10 Apr
Amazing Lakefront Pool On Coveted Horseshoe Bend!

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 AU$403
includes taxes & fees
12 Apr - 13 Apr
Summer Serenity Waterfront Condo!- Indoor Pool!

Top Floor 2Bd 2Bath Condo at Lighthouse Landing!

Top Floor 2Bd 2Bath Condo at Lighthouse Landing!
Lake Ozark
9.4 out of 10, Exceptional, (6 reviews)
"Excellent accommodations and check-in and check-out were a breeze. Very pleased with entire trip. "
United States
Nick A.
The price is AU$494
includes taxes & fees
9 Apr - 10 Apr
Top Floor 2Bd 2Bath Condo at Lighthouse Landing!
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 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$251 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?

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.