Holiday rentals in Oskaloosa

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Top-rated holiday rentals in Oskaloosa

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A hot tub sits invitingly, surrounded by a lush green landscape. Gentle bubbles rise from the water, offering a sense of relaxation. In the background, rolling hills and trees provide a picturesque setting under a clear blue sky.
Farm stay in Weston
4.93 out of 5 average rating, 384 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.

Top guest favourite
A private outdoor space features a hot tub with a wooden cover, surrounded by a gravel area and bordered by a wooden fence adorned with decorative designs. A light blue chair provides a seating option next to decorative wooden panels.
Tiny home in Tonganoxie
4.99 out of 5 average rating, 385 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
The octagonal cottage is surrounded by a well-manicured lawn and features a stepping stone pathway leading to a patio area. Large windows with shutters offer natural light, and a small air conditioning unit is visible on the side of the structure.
Guest house in Eudora
4.89 out of 5 average rating, 249 reviews

Cozy cottage getaway in garden paradise

Get away and relax in a whimsical octagonal cottage surrounded by a lush garden, overlooking a aqua pond and the Wakarusa river. You will have everything you need for a romantic date night or an inspiring place to slow down and reconnect with nature. •1 bedroom open living space with lots of natural light and beautiful views. • Coffee cart with microwave and electric burner and mini frig are provided. • Paddle boat at the lower pond & 2 disc golf nets available for fun. •NO PETS ALLOWED

Top guest favourite
A serene outdoor setting features a winding path illuminated by soft lights, bordered by stone and lush grass. Torches are positioned along the path, creating a calming ambiance. The space is surrounded by trees, offering a sense of privacy and natural beauty.
Barn in Lawrence
4.94 out of 5 average rating, 353 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

Guest favourite
Home in Lawrence
4.94 out of 5 average rating, 228 reviews

Disabled access king bed, massage chair, near I-70

This duplex is the perfect stop for a weary traveler! Sleep in a Big king-size bed or an adjustable queen bed! Garage to park in. This place is fully disabled accessible. One level, anti-allergen hardwood floors throughout. Walk-in shower with grab bars. Raised commode. For living room comfort,we provide a massage chair, power recliner sofa, Xbox Game system, and TV with premium channels on Roku! Kitchen is very open and fully stocked. 10 minutes from KU & downtown 5 minutes to i-70.

Top guest favourite
Guest house in Eudora
4.95 out of 5 average rating, 183 reviews

Relaxing Vineyard Getaway

BlueJacket Crossing Vineyard is a small, family vineyard located in Northeast Kansas, west of Kansas City, just 5 miles east of Lawrence, Kansas home of the University of Kansas. The space is designed as a small apartment adjacent to the Winery. The 1st floor houses the Living Room (with TV/Cable/Internet), Queen Fold Out Sofa, Small Kitchenette, Breakfast Bar, & Bathroom/Shower. The 2nd floor is the Master Bedroom with King Bed, & French Doors to a Deck overlooking the Vineyard.

Guest favourite
A hot tub is positioned outdoors amidst lush greenery and tall trees, offering a tranquil setting. The water surface reflects the surrounding foliage, creating a serene environment for relaxation.
Guest suite in Topeka
4.95 out of 5 average rating, 156 reviews

Located on Beautiful Lake Shawnee! 2 BDRM, 1 BATH.

Located in the SW area of Lake Shawnee within walking distance to many of the lake’s amenities such as the tennis courts, sand volleyball, playground, shelter house three, the south boat ramp, and the walking/bike trail. It’s close to both gazebos & the rose garden - popular wedding venues. It's great for a romantic getaway or a long weekend. Enjoy sunrises over the lake with a hot cup of coffee on the patio. And there’s a hot tub and pool to enjoy during your stay.

Top guest favourite
A bright dining area is showcased, featuring a wooden table surrounded by four chairs. Large windows allow natural light to fill the space, offering views of the surrounding landscape. Floral centerpieces enhance the inviting atmosphere, while cozy seating is visible along the window ledge.
Home in Kansas City
4.98 out of 5 average rating, 458 reviews

Enjoy Nature at Modern Farmhouse Close to City

The perfect getaway that's close to it all! Enjoy your privacy at our restored 1933 bungalow on 18 acres just minutes off I-70. Relax after a road trip or gather your friends for a concert. Soak in the tub and get your best night of sleep on a plush mattress. Cook in a stocked kitchen or eat out at restaurants five minutes away. Meander along mowed paths, and let the kids play! We are pet-friendly, and business-ready with Gigabit Internet and an office setup.

Top guest favourite
The exterior of a single-story home is showcased, featuring a light gray facade with three large windows. A simple landscaped area is present in front, with a concrete pathway leading to the entrance. Trees are lightly visible in the background.
Home in Topeka
4.85 out of 5 average rating, 198 reviews

Capital City Cottage

Entire abode to yourself! Two bedrooms with queen beds, one bath. Off street, covered parking. Roku is available on the TV, for you to log in to your preferred choice of viewing pleasure. Close to VA Med Center & Washburn Univ. Minutes from State Capitol & Downtown. Centrally located from downtown and west side ( where all the chain stores and restaurants are located). NO parties are to be hosted in our house. NO smoking of any kind inside the house.

Top guest favourite
Cabin in Tonganoxie
4.96 out of 5 average rating, 870 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.

Top guest favourite
An open-concept living area features a spacious sectional sofa and a circular coffee table adorned with fruit. Large windows allow natural light to illuminate the interior, while decorative plants add a touch of greenery. Industrial elements are highlighted by exposed ductwork and a stone accent wall.
Loft in Lawrence
5 out of 5 average rating, 145 reviews

On Mass St • Stylish, Quiet & Super Cozy Stay

Stay right on Mass Street in this spacious 1,400 sq ft open-concept loft designed for comfort, light, and walkable convenience. Despite its central location, the space is calm and comfortable inside, making it easy to relax after a day downtown. Enjoy modern finishes, generous living areas, and quick access to dining, shopping, and KU. Ideal for couples, friends, or families who want space and location without sacrificing comfort.

Top guest favourite
A tiny house made of wood stands surrounded by cedar trees, with a wooden deck leading to its entrance. A small table with two chairs is placed nearby, illuminated by hanging lights, providing a serene outdoor seating option.
Tiny home in Perry
4.96 out of 5 average rating, 583 reviews

The Batch - Tiny House Living

Located 20 minutes from downtown Lawrence, the Batch is a sustainable tiny house nestled in the cedar forests of Perry, KS. Decorated in a minimalist southwestern style, this tiny cabin is a serene and peaceful setting for souls seeking restoration, quiet, and the healing qualities of the woods. Or just a great place to getaway with your love or friends with an even greater view!

Popular amenities for Oskaloosa holiday rentals

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