Holiday rentals in Ottumwa

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!

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.

Travelers / corporate housing / hospital workers

Come and enjoy a peaceful, quiet neighborhood at Granny's Place. As you walk in the door, you will feel at home in the spacious entire first floor of the house consisting of two bedrooms and a beautiful sunroom dining area to enjoy a morning cup of coffee. A washer/dryer combo is located between the bedrooms for convenience. This house is centrally located and only 1 mile away, and less than 5 minutes from the hospital if that is your temporary place of employment. A place to relax!

The Short Stay

Situated on the second floor of a historic mid-1880s Main Street building, this smoke-free, pet-free apartment blends charm and modern convenience, catering exclusively to adult guests. Featuring a contemporary layout, quality amenities, and a prime location within walking distance of local bars and eateries, it also offers easy access to our mercantile and hidden speakeasy (21+). Ideal for visitors and professionals seeking a comfortable, temporary stay in Downtown Ottumwa.

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.

Dixon Block Loft

Dixon Block loft is a historical building renovated into a beautiful 2 bedroom loft apartment. Old historic charm is embedded into the style. Overlooks charming town square. Walking distance to stores and restaurants. We live locally to assist with anything needed. We can't wait for you to enjoy the local small town charm. Many events happen in December, Lighted Christmas Parade. In the summer time, the town square has many concerts.

O Town Cozy Cottage

Discover your perfect cozy hideaway! This relaxing one-bedroom, one-bath home is nestled on a quiet street, offering hotel-like convenience with all the comforts of home. Unwind in a space designed for comfort and ease, while staying just minutes from shops, dining, and local attractions. Whether you're visiting for work or leisure, you'll love this peaceful retreat that’s close to everything you need yet feels worlds away.

Lovely 1 or 2 bedroom apartment.

Beautiful private setting, fully furnished modern apartment available as 1 or 2 bedroom in central part of the city. This property is centrally located in Ottumwa. Within five minutes of the hospital, John Deere facilities, JBS facilities, high school, restaurants, courthouse, park, downtown within 5 to 10 minutes of the mall area. Several churches in the area. No animals allowed.

Fran's Cottage

🏡 Your Ultimate Getaway Awaits! 🏡 Step into a world of comfort and charm at this delightful house, where every corner exudes relaxation. With a generous 950 sq. ft. of space, you'll find room to breathe and unwind. 🌟 Discover 2 cozy bedrooms offering the perfect retreat after your adventures. Nestle into a snug queen bed or opt for a full size bed in the 2nd bedroom.

Country getaway

Plan your next family getaway at our home! Nestled in a peaceful, country setting. Just minutes from town! Enjoy the quiet space that includes a pool, large deck, grill, hot tub and a pond! We have three bedrooms and two areas that can be used for bedrooms with an air mattress! This is perfect for a few families to get together for a long weekend as well!

Droptine Cottage

A back road get-away in Iowa's best deer country. Featuring all the comforts of home with 2 bedrooms (1 queen & 1 full/twin bunk bed). Relax outside on the deck or by the firepit. Perfect for a group of hunters, fishermen or a family visiting the Villages! Included TV, DVD, Washer & Dryer, Wi-Fi, Charcoal & Gas Grills. Daily or weekly rentals available.

Spacious Guesthouse in Oskaloosa

This spacious rental resides in a quiet neighborhood, just a short walking distance from the local University and the historic downtown. You will enjoy a fully stocked kitchen, a relaxing living space, and all the conveniences of home.