Vacation rentals in Olean

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Top-rated vacation rentals in Olean

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Guest favorite

Cottage in California

4.96 out of 5 average rating, 115 reviews

Restored cottage built in 1906 (2 bed/2 bath)

Looking for a nice place to stay close to Jeff City? Spend a few nights in this restored cottage built in 1906! You are sure to be comfortable in this great little hideaway! The cottage has period appropriate furnishings with all the modern amenities! This historic property is located on a quiet street near an elementary school. California is a great location. We are an easy 25 minute drive to downtown Jefferson City and situated halfway between St. Louis and Kansas City right off Highway 50!

Guest favorite

Home in Jefferson City

5 out of 5 average rating, 111 reviews

A *Spicy* Couples Getaway at DungeonJC!

DungeonJC is the ultimate retreat for adventurous couples who are looking for a truly unforgettable experience. Our 114-year-old brick bungalow has been completely transformed into a stunning, fully outfitted dungeon space that's perfect for indulging your deepest desires. Whether you're a seasoned kinkster or a curious newcomer, our immersive environment is designed to take your breath away. You'll be transported to a world of sensuality and pleasure, where every detail is crafted to inspire.

Guest favorite

Home in Bonnots Mill

4.96 out of 5 average rating, 282 reviews

Secluded "Heaven": soaker tub, sauna, sunset view

"Heaven" ( 1,512 sq ft, 7 ac) sits on a bluff overlooking the Osage river. An open home with huge full length windows and a sun room provides abundant natural lighting. Two porches offer views over the river and to the woods. A soaker tub and sauna are situated in the cabin with a view to the sunset. The cabin is at the end of a secluded forest road. A locked garage is available for parking small cars. Drive: 15-20 min to Linn for supplies / 30 min to Jeff City / 5 min to public river access.

Guest favorite

Condo in Osage Beach

4.93 out of 5 average rating, 178 reviews

Lake Life Reimagined -best location best view 17mm

Escape from the concrete jungle and rejuvenate your energy with a stay at this Osage Beach condo! Featuring a panoramic view of the Lake of the Ozarks from your very own deck, this 1-bed, 1-bath vacation rental is a modern retreat close to shopping, recreation, and entertainment venues. Spend the day cruising the coastline and enjoying water activities like fishing, jet-skiing, tubing, and more! Finally, head home and fire up the gas grill for a pleasant evening of good food and quality time.

Guest favorite

Condo in Lake Ozark

4.84 out of 5 average rating, 345 reviews

Large, Great View, Fully furnished Luxury 3bd 2ba

Awesome Lake of the Ozarks location off Hwy HH close to the Lodge of the Four Seasons, great restaurants, nightlife, golf, and family friendly activities. 3 bed, 2 bath luxury condo with a gorgeous lake view, three season room accessible from the living room and each bedroom, master bedroom suite and stainless appliances. Great for couples, solo, business travelers, families with kids, and groups. Walking distance to the Regalia Hotel huge swim up bar pool & restaurant. Access to POA gym.

Guest favorite

Condo in Lake Ozark

4.98 out of 5 average rating, 127 reviews

Lakescape Romantic Retreat w/ Hammock

"This is IT!" 3mm Million Dollar Main Channel Panoramic View, Walk-in Level Entry, Two 58" Roku TV's, King Sized Bed, Electric Fireplace, Screened-in Deck, Electric Blackstone Griddle, Salt-water Pool, Deck Furniture, Papasan Lounger, Keurig Coffee, 400mbps WiFi... and a hammock! The perfect retreat for couples, but big enough for a small family... we'd love to host you at Lakescape Romantic Retreat! We believe our condo checks so many boxes that you'll say, just like we did, "This is IT!"

Guest favorite

Home in Gravois Mills

4.97 out of 5 average rating, 140 reviews

*Wow, Luxury 5BR, 4BA Edgewater Escape w/ Hot Tub!

This phenomenal lakeside home has 5 bedrooms, 4 baths, hot tub, swim dock and is built for entertaining with over 3000 sq ft of space! Enjoy swimming in the quiet cove and take advantage of our two kayaks, peddle boat, & fishing. Inside, enjoy our gourmet kitchen, shuffle board, foosball table, games and multiple decks to enjoy the view! Located on the 7MM just a few minutes by water to H Toads and Shady Gators. With space to sleep your entire family & friends, come relax with us!

Guest favorite

Rental unit in Village of Four Seasons

4.92 out of 5 average rating, 101 reviews

No Stairs! Hot Tub! Indoor/Outdoor Pool! Boat Slip

12 MM Lake Views + Deck + Hot Tub + 2 pools! Indoor and Outdoor Pool with views!! Make yourself at home! This condo boasts new furnishings! This condo is located in a very popular complex on Horseshoe bend, just minutes from the Bagnell Dam strip and Osage Beach. Guests enjoy access to a lakefront pool, clubhouse with indoor pool and hot tub(opening early October 2024), playground, tennis court, basketball court and private boat launch. Amazing sunset views from the relaxing deck!

Guest favorite

Home in Lake Ozark

4.99 out of 5 average rating, 140 reviews

Awesome Lakefront A-Frame Cabin! Unique, Cozy Interior-Private Dock-Great Location!

Experience the Ultimate Lake Ozark getaway in this unique, newly renovated A-FRAME! If you’ve never stayed in an A-Frame, you’re going to want to stay here…situated in a cove, the bright and airy 3-bedroom, 2-bath cabin offers serene views and a modern interior. It has plenty of “Selfie Walls" & an outdoor living space with a private dock full of fun! It’s located near many attractions like the infamous Bagnell Dam Strip. Perfect for relaxing, fishing, or wet and wild fun!

Guest favorite

Yurt in Holts Summit

4.99 out of 5 average rating, 324 reviews

Yurt in the Forest

Step into the serenity of trees and sky. The yurt has been crafted to relax and refresh you with comfort and convenience and the simple joys of peaceful proximity to nature. The round common room has a kitchenette, queen-size bed, table, chairs, and a futon which opens out to a double bed. A shower room completes the setting. And now no additional cleaning fee!. also, the water is from our deep well: tested, certified.... And delicious!

Guest favorite

Farm stay in California

4.93 out of 5 average rating, 221 reviews

The Shouse

The Shouse is a rustic living quarters built directly under the same roof as our horse stable. Bring your horses along and they can stay here too. The home has recently been fully renovated from an Amish tack shop. It is located in the heart of an Amish community. Spend your evenings relaxing on the front porch and watch the horse and buggies go by. Ask about booking your own buggy ride while you stay to get the most out of your visit!

Guest favorite

Condo in Camdenton

4.97 out of 5 average rating, 327 reviews

Lakeside Condo w Kayaks & Pools

Relax and catch the lake breeze on the balcony of this quiet condo on the Niangua Arm of the Lake of the Ozarks. Right off highway 54, but tucked away from the hustle and bustle. Just minutes from Ha Ha Tonka State Park, two golf courses and tons of amenities in nearby Camdenton and Osage Beach and lots of lake fun! 2 adult kayaks, 2 pools, a playground, horseshoe pitch, beach volleyball court and a large lawn for family games.