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Holiday houses in Oskaloosa

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Quick stats about holiday rentals in Oskaloosa

  • Total holiday rentals

    Explore 20 holiday rentals in Oskaloosa

  • Nightly prices starting at

    Oskaloosa holiday rentals start at $72 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,100 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Oskaloosa holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Oskaloosa rentals

  • 4.9 Average rating

    Oskaloosa stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated holiday rentals in Oskaloosa

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

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Guest favourite
Home in Oskaloosa

Sunny Cottage: FirePit, by Prairie & Wooded Trails

This bright, cheerful two bedroom home with full service kitchen, vaulted open living area, smart Weber grill, fire pit and private backyard is tucked away in a quiet neighborhood with easy access to a 14 mile paved recreation trail, nearly 1700 acres of forests, wetlands, prairies and parks to explore, local winery with dine in nights, cheese farm, museums and active art community. Guests will have easy access to the home with keyless entry. You'll find yourself rested, refreshed and reignited!

4.95 out of 5 average rating, 152 reviews
Top Guest favourite
Apartment in Brooklyn

The Attic on Front

Welcome to your home away from home in the heart of historic Brooklyn, Iowa! Located on the second floor of a downtown building, this space includes a full kitchen, office nook, bathroom, and a large living area with sleeping quarters. Enjoy beautiful downtown views, just steps from the Michael J. Manatt Community Center and Brooklyn Opera House. Centrally located between Des Moines and Iowa City, with easy access to I-80, this is the perfect spot to experience Brooklyn's charm and history.

4.99 out of 5 average rating, 135 reviews
Top Guest favourite
The exterior of a remodeled house is adorned with warm white lights, highlighting the entrance. A porch with two chairs is visible, alongside decorative plants and stones. The landscape features a welcoming pathway leading to the front door, surrounded by winter foliage.
Cottage in Pella

The Strawtown Cottage - in downtown Pella

Completely remodeled 1865 original Strawtown Store of Pella conveniently located in one of the best small towns in Iowa. Three blocks to downtown Pella, 1 1/2 blocks to West Market Park, 2 blocks to Central football, baseball and softball complex. Enjoy the cottage charm with two private bed and bath suites, a family room with dining, full kitchen, front and side porch, laundry and large back yard. Off-street parking in the back. Luxury sheets on queen beds await after your adventures.

4.99 out of 5 average rating, 422 reviews
Top Guest favourite
A spacious studio apartment with an open floor plan is highlighted. Two reclining sofas are arranged around a coffee table, while a dining area features a table with white chairs. Natural light enhances the overall space, which is finished with modern flooring.
Apartment in Oskaloosa

Downtown Oskaloosa Square

Brand new in 2021! 650 sf studio apartment in downtown Oskaloosa. Located on 3rd floor of commercial building, across the street from the iconic bandstand and Oskaloosa square. Elevator access to private 3rd floor. 10 foot ceilings, washer & dryer in unit, (2) 50" smart tvs with high speed wifi and cable tv included. Nectar memory foam Queen mattress, double reclining sofa. Plenty of closet space and furnishings for long stays. Professional property management office on main floor.

4.94 out of 5 average rating, 218 reviews
Top Guest favourite
Home in Pella

Pristine getaway for groups; 5 BR - sleeps 16+

Wildflower on Independence was designed to provide you with a relaxing, spacious, peaceful house to gather with family and friends! With five bedrooms, a fully equipped kitchen, open dining room, seven TVs, capacious family room, and beautiful bathrooms, you will have ample room to relax and fellowship. Whether you are planning a family reunion, girls getaway, or bridal shower, Wildflower will not disappoint! Come and be our guest while you enjoy the history and flavor of Pella, Iowa.

5.0 out of 5 average rating, 137 reviews
Top Guest favourite
Home in New Sharon

Niland Nook

Relax with the whole family at this wonderful 3 bedroom, 2 bath house nestled in the farming countryside. Whether you're in the cozy living room, sitting out in the screened in porch, or spending time in the backyard....this house has all the amenities to make your stay an enjoyable one. Cows and calves can be seen for that added country experience. Several local attractions and nearby activities are just 15 minutes away in Oskaloosa, Iowa. Just a short 27 miles from Interstate 80.

4.98 out of 5 average rating, 52 reviews
Top Guest favourite
The exterior of the cottage is displayed, showcasing a gray facade with white trim. Two doors are visible, one leading into the home and another to a small utility space. Soft outdoor lighting highlights the entrance, while a manicured yard with green grass surrounds the structure.
Cottage in Oskaloosa

"The Lost Gem" A little bit country...

Get ready to enjoy good 'ole country livin' when you choose to stay at our little cottage, The Lost Gem. Its a quiet retreat, recently renovated on a hard surfaced road with all the privacy you could desire. The yard is large enough to sit outside, giving children area to run .While enjoying the spacious outdoors, you'll be able to gaze at the beautiful sunsets each day. The entrance is very accessible and well lit to welcome you. Our guests enjoy a single level home with no steps.

4.97 out of 5 average rating, 66 reviews
Top Guest favourite
A spacious living area features a black leather couch and a wooden coffee table on a textured area rug. Light wood flooring complements the neutral walls. In the background, a kitchen with dark cabinetry and bar seating is visible, enhancing the openness of the space.
Loft in Montezuma

Monte Lofts, on the square.

Welcome to Monte Lofts in downtown Montezuma. This spacious, newly remodeled loft is smoke free and pet free. The loft features a private, secured entrance, a huge, fully stocked kitchen with stainless steel appliances and a laundry room with front load washer and dryer. The bedroom features a large walk in closet and its own entrance to the laundry room and full bathroom. The living room, with floor to ceiling windows offers a great view of the historic downtown Montezuma square.

5.0 out of 5 average rating, 101 reviews
Top Guest favourite
The entrance of the home features a welcoming front porch with two rocking chairs. The exterior showcases a combination of blue siding and natural stone accents, complementing the charming wood garage door. A sweeping driveway leads to the inviting entrance.
Home in Oskaloosa

Luxury Lakefront at Lake Keomah

Welcome to your upscale lake retreat in Keomah Village, Oskaloosa, Iowa — where refined comfort meets lakeside relaxation. Just steps from Lake Keomah, this beautifully curated home offers everything from elegant finishes and serene outdoor spaces to family-friendly features and year-round entertainment. Relax on the inviting front porch, where two rocking chairs welcome you to slow down, breathe in the fresh air, and begin your perfect getaway.

5.0 out of 5 average rating, 19 reviews
Top Guest favourite
A well-appointed living room features a spacious sectional sofa, paired with a wooden coffee table. Natural light streams through large windows, accentuated by light curtains. A modern armchair and floor lamp provide additional seating and illumination. A television is mounted on a wooden console, with decorative elements enhancing the space.
Home in Pella

Modern Downtown Retreat In The Heart Of Pella

Enjoy the convenience of being a block from Pella’s square and all that the downtown area has to offer. This fully remodeled, 3 bedroom, 2 bath home offers you a centrally located base to plan your daily excursions. Whether your day is spent perusing the unique shops around the square, on the trails or water at Lake Red Rock, or meeting up with friends and family, this home will be the perfect place to recharge and refresh between activities.

5.0 out of 5 average rating, 179 reviews
Top Guest favourite
A serene pond reflects the colors of the sky during sunset, surrounded by lush green grass and scattered trees. The property is observed in the background, framed by the branches of nearby trees, creating a peaceful and natural setting.
Home in Pella

Songbird Hideaway

If you are searching for a unique and tranquil retreat amidst nature's beauty, Songbird Hideaway is a great choice. The 2 bedroom, 2 bathroom home with a modern western vibe features a secluded property overlooking a pond, an expansive yard, and walking trails throughout the grounds. The relaxing and peaceful atmosphere is a superb place to unwind or spend quality time with family and friends.

5.0 out of 5 average rating, 59 reviews
Guest favourite
Home in Eddyville

Home In Eddyville

New little one bedroom home in a quiet little town. Located by the city park and walking distance from three restaurant/ bar and grills along with the view of the DesMoines River within walking distance. We live about 6 mins away, so we can be available if needed. Place has high speed Wifi.

4.93 out of 5 average rating, 88 reviews

Popular amenities for Oskaloosa holiday rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Oskaloosa

Top Guest favourite
The spacious living area features large windows that frame scenic views of greenery, with natural light illuminating the room. Soft, neutral-toned sofas and vibrant yellow chairs complement a round coffee table, while decorative elements like a cozy throw and a textured pouf add warmth.
Home in Pella

TheGuesthouse, 2BR2Bath, KING bed, QUIET Hideaway

5.0 out of 5 average rating, 47 reviews
Top Guest favourite
Barn in Pella

Sandstone Creek Barn

5.0 out of 5 average rating, 22 reviews
Top Guest favourite
Home in Pella

The Mid-Town Cottage

5.0 out of 5 average rating, 43 reviews
Top Guest favourite
Home in Pella

Mid-Century Modern Retreat

5.0 out of 5 average rating, 43 reviews
Top Guest favourite
The exterior of a charming cottage-style home is showcased, featuring a dark blue facade, a brick chimney, and a welcoming front porch with large windows. Lush green lawn and neatly trimmed landscaping enhance the inviting curb appeal. A driveway leads to the attached garage.
Home in Pella

Warm, inviting home in the heart of Pella

5.0 out of 5 average rating, 96 reviews
Top Guest favourite
A spacious farmhouse is surrounded by lush green grass, with a large driveway and trees in the foreground. The house's brick exterior features multiple windows, blending harmoniously with the rural landscape and farmland visible in the distance.
Home in Otley

Woodland Estate

4.96 out of 5 average rating, 25 reviews
Guest favourite
Home in Ottumwa

Country getaway

4.84 out of 5 average rating, 19 reviews
Guest favourite
The grand brick estate is presented, featuring multiple gabled roofs and a welcoming front entry. Surrounded by landscaped gardens and manicured lawns, an inviting circular driveway leads to the main entrance. A private pool can be seen in the backyard, framed by lush greenery.
Home in Knoxville

Home w/ Pool/Hot Tub- Knoxville/Pella/DesMoines IA

5.0 out of 5 average rating, 14 reviews

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Oskaloosa?

    Oskaloosa has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in hotel rentals in Oskaloosa?

    Experience the best of Oskaloosa with our hotel rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Oskaloosa?

    Yes! Work meets play with ease at over 10 vacation rentals in Oskaloosa featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do hotel rentals in Oskaloosa have air conditioning?

    Absolutely! We offer over 10 hotel rentals with air conditioning in Oskaloosa. Enjoy a tailored experience with all the comforts you desire.

  • Do hotel rentals in Oskaloosa have wifi?

    Absolutely! We offer over 10 hotel rentals with wifi in Oskaloosa. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Hotel Rentals in Oskaloosa?

    Enhance your stay in our Hotel Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.