Holiday rentals in Oskaloosa

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Top-rated holiday rentals in Oskaloosa

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Top guest favourite
A spacious living area features original hardwood flooring and exposed brick walls. Comfortable seating options include a leather sofa and armchair. Large windows allow natural light to fill the room while potted plants add a touch of greenery to the inviting space.
Loft in Leavenworth
4.97 out of 5 average rating, 401 reviews

Follow Lincoln's Steps at Queenie's Loft in Leavenworth

Look out at the pristine City Hall with the Statue of Liberty and a bronze sculpture marking the city where Honest Abe visited just before announcing his run for Presidency. The original bricks and hardwood in this unique 170-year-old home have stood the test of time. Take a an elevator (or stairs) to the 2nd floor. Located in the heart of historic downtown Leavenworth, the First City of Kansas. Within a few blocks are several coffee shops, bakeries, boutiques, and bars. Located only 10 miles from the award-winning tourist town of Weston, which has many breweries, wineries, and hiking trails. You won't find this anywhere else! Original wide hardwood floors that were laid 165 years ago and the original brick walls that have stood the test of time. A view from nine windows that overlook our pristine city hall with the statue of liberty and statue of Abraham Lincoln. (Lincoln announced his run for presidency right there in Leavenworth!) And to think, he most likely walked across the street and came in our building as it was a saloon at the time! You will enter our loft from the street by keypad and there is a small room leading to our new elevator (big steel door) to take you to the 2nd floor. Directions for the elevator are on the wall. Very easy, just always close the white accordian door to elevator in case your party calls it from another floor. Your party is the only people who have access to this elevator. Check in is between 4 and 7pm. Please drop us a text if it is not in that time frame. Check out is 11am. Again, please drop us a text if you need more time! Mac and Stacy are always just a text away and can be there within 10 minutes. #913-651-7798. Text us with any questions! Ride a custom elevator to the open yet cozy space above the host's candle and gift boutique. The flat is a great base to explore KC, Fort Leavenworth, the county seat, and quaint Weston, MO. Shops, restaurants, coffeehouses, and bars are steps away. There is a large parking lot behind the building on 5th street. 65" tv, but we do not have cable. There is a dvd player, and you are welcome to hook your phone to the tv to watch your prime video, hulu, etc. That is what we do, and use the data from our phone or computer to display on the tv screen!

Top guest favourite
Three horses graze on lush green grass under a glowing sunset. The sun casts a warm light across the landscape, creating a serene backdrop. A dog is visible nearby, adding a friendly element to the peaceful countryside scene.
Farm stay in Weston
4.93 out of 5 average rating, 392 reviews

Hippie Hills-FIFA World Cup 2026 near Kansas City

FIFA World Cup Visitors: We speak Dutch, German & Swiss German. LGBTQ friendly. Like a storybook, but with Wi-Fi, a hot tub, and a hospitality crew. Dogs Taco, Ally, and Bullet greet you at your car, frisbee in tow and zero chill. Donkeys Slim and Shady expect breakfast negotiations, while cats Potato and French Fry judge from afar. Horses Pieces and Jasper love head scratches. Historic Weston is 5 minutes away with shops, wineries, and charm. After exploring, unwind in hot tub under the stars.

Guest favourite
A cozy living area is equipped with a large leather couch adorned with decorative cushions. A massage chair is positioned nearby for relaxation, while a coffee table adds functionality. Natural light filters in through a large window, framed by soft curtains, enhancing the inviting setting.
Townhouse in Lawrence
4.96 out of 5 average rating, 361 reviews

cowboy house Massage chair, near I-70, fenced yard

License STR-18-00048. Rare find! Welcome to western style ranch nestled right in the center of town. Walking distance to a park, food & shopping. Just minutes from KU & downtown. The kitchen sports a convection oven stove, dishwasher, full-size microwave, full-size fridge, and lots of counter space. Shady backyard to play in and a fenced-in side porch for relaxation or dog. For your convenience, we provide a full-size washer, dryer & desk to catch up on school/office work. Popular! book now!

Top guest favourite
A well-lit bedroom features a spacious bed with a grey quilt and a second smaller bed, both flanked by bedside tables and lamps. Artwork depicting cowboys adorns the walls, and natural light filters in through a window covered by curtains.
Home in Ozawkie
4.97 out of 5 average rating, 123 reviews

Bunkhouse

♥️Perry Lake ,Ozawkie KING BED. Attention outdoor enthusiasts! This 1800-square foot ranch features three bedrooms, two baths, and an open floor concept that is great for entertaining or kicking back after a long day on beautiful Lake Perry. ✔ 3 min.away from Old Town boat ramp and campground . ✔8 min to village green golf course 5 min crooked post winery. ✔Pet friendly, family reunion friendly. ✔8 beds, 2 bathrooms, 3 tvs. Free WiFi ✔big yard, corn hole boards. Boat parking/trailer .

Top guest favourite
The exterior of the cottage features a green facade with a welcoming entrance. A decorative wreath hangs on the door, accompanied by seasonal decor on a shelf. A vibrant red wagon and wooden seating are visible, along with a stylish wooden privacy screen and a covered entry area.
Tiny home in Tonganoxie
4.99 out of 5 average rating, 390 reviews

Kathy's Kottage (near Legends)hot tub-fire pit

First of - Kathy’s Kottage offers a uniquely private, warm and inviting detached cottage. We are not a huge commercial venture, but owned, operated, maintained, and cleaned by hosts who live within 150 yards. The Kottage is our only offering. We charge a cleaning fee of $35 a stay, so there isn't a list of chores at check out. We take up to 4 hours between every stay to extensively clean and disinfect every surface. We are proud of the Kottage as shown in every review over the last four years.

Guest favourite
An outdoor seating area is set in a spacious yard, featuring red benches arranged around a fire pit. A brick home with a sloped roof and front porch is visible in the background, surrounded by shade trees and green grass.
Farm stay in Auburn
4.9 out of 5 average rating, 375 reviews

Charming Farm Retreat Near Topeka, KS

🌾 Escape to Hidden Hill Farms, just 20 minutes south of Topeka! Our 4‑bed, 3‑bath farmhouse sits on an 80‑acre working farm with shady cottonwoods, a spacious deck, cozy fire pit, and peaceful countryside views. Families love our hands‑on farm tours—feed chickens, collect eggs, and meet the cattle. Inside, enjoy a fully stocked kitchen, Wi‑Fi, streaming TV, board games, and family‑friendly amenities. Perfect for reunions, retreats, and multi‑generational getaways filled with lasting memories.

Top guest favourite
A warm living area showcases a wooden accent wall and a stone fireplace. A comfortable sofa is paired with a coffee table and two stools near a kitchen island. A TV is mounted on the wall, while natural light enters through a nearby doorway.
Guest house in Topeka
4.97 out of 5 average rating, 418 reviews

Quiet Countryside Retreat. No pet fees!

Enjoy our piece of country paradise! 1 BR lodge sleeps 4 comfortably w/fully equipped kitchen, W/D, fire pit & grill. Relax at our peaceful lodge after hunting at nearby Ravenwood Lodge or escape with the family. Spacious walk-in shower. Breakfast items & great coffee options provided! You may see pheasant, quail & deer on the property. Near Echo Cliff park & on the edge of the Flint Hills. No pet fees!! Low cleaning fees & no occupancy tax! Early check in/ late check out may be available.

Guest favourite
The ranch-style home is set on a spacious corner lot, framed by large trees. A large driveway leads to a two-car garage and carport. The exterior features a mix of stone and wood, complementing the natural landscape.
Home in Leavenworth
4.95 out of 5 average rating, 158 reviews

Family, Pool, Business, Dog, Arcade and Toys

Three bedrooms (one queen and four twin), two tiled bathrooms, a twin-over-twin bunk and a sleeper-sofa. House sleeps nine comfortably. Six smart TV's. Dogs allowed! Large, fenced backyard. Two washers and two dryers. Basement is dedicated playroom and has a large arcade, pool table, skee ball, foosball, basketball machine, Barbie House and play kitchen. Dozens of board games and outdoor toys. Ultra-fast internet. Easy 20-minute drive from both from the airport and Legends Mall and Plaza.

Top guest favourite
A cozy barn exterior is adorned with warm white string lights along the roofline. A welcoming entrance with a white door is visible, along with a few windows. The surrounding grassy area features flowering plants and a shaded sitting area with chairs.
Barn in Lawrence
4.94 out of 5 average rating, 358 reviews

The Barn in The City.

NO CLEANING FEES. Take it easy at this unique and tranquil getaway. Cozy converted barn. Sleeping loft, NOTE: The sleeping loft has a maximum height of 5'1". very short walking distance to MANY bars and restaurants, 3 blocks from Allen Fieldhouse, near K.U. campus, just off K-10 and Hiway 59 junction. Off-street parking. 2 Amazon Fire T. V.'s with Wi-Fi, streaming and antenna T.V. Please Note: A 3rd guest will incur an additional charge of $35.00 A 4th guest is an additional $20.00

Top guest favourite
A bright living area features large windows framing views of the surrounding nature. Comfortable seating includes a blue sofa with orange cushions and two accent chairs. A colorful area rug lies beneath a coffee table, enhancing the spaciousness of the room.
Earthen home in Perry
4.99 out of 5 average rating, 101 reviews

The Meadow - Modern Strawbale on 10 Private Acres

Take it easy at this unique and tranquil getaway. The Meadow house, a modern strawbale home, is surrounded by creeks and woodlands on ten secluded acres. Explore the surrounding woods, relax on the spacious deck and take in the stars, and plan adventures in nearby Lawrence and at Perry Lake Inside the home, curl up in a peaceful corner to enjoy a book, challenge family and friends to various games in the rec room, and enjoy meals from the modern kitchen with all the amenities.

Guest favourite
A spacious studio features a comfortable bed, a colorful blue dresser, and a futon. A large wall map adds character to the room, while a flat-screen television is mounted nearby. Natural light fills the space through a window with a minimalist window unit above.
Guest suite in Ozawkie
4.91 out of 5 average rating, 115 reviews

Rock Creek Studio Neighboring Lake Perry

Voted one of the top Airbnbs to stay at in Kansas & the most affordable! Fully equipped kitchen, stove, microwave, Starlink & 55' Roku Satellite HD TV, patio, & picnic area. Relax in our newly remodeled first floor studio nestled in the back of the guesthouse garage w/ separate private entrance. Located within a 3 minute walk to the Rock Creek Marina where you can kayak, fish, jet ski, boat or fish off the dock. Golfing, hiking, biking, ATV trails are minutes away.

Top guest favourite
A newly renovated log cabin is surrounded by lush greenery, offering a tranquil entrance. A stone pathway leads to the rustic wooden door, while a picnic table is positioned nearby under the shade of a tree, enhancing the inviting outdoor space.
Cabin in Tonganoxie
4.96 out of 5 average rating, 881 reviews

Cozy Cabin Retreat

Escape to our cabin which earned top-rated Airbnb in all of Kansas for a cozy, quiet getaway. Ideal for unwinding and rejuvenating after the demands of a hectic day. Enjoy scenic hiking trails, axe throwing, horseshoes, or a peaceful walk through our labyrinth. End the day with a stunning sunset over the valley from our swing. Just 5 minutes from the lake! Note: The cabin is on a shared property with a retreat center, Sacred Hearts Healing.

Popular amenities for Oskaloosa holiday rentals

  1. Airbnb
  2. United States
  3. Kansas
  4. Jefferson County
  5. Oskaloosa