🏡 Vacation Rentals & Retreats

Gather and be refreshed at The Cabin! This beloved cabin is nestled between farmland, where the sun rises and a lake village over which the sun sets. With nearly 2 acres of private yard with a pool, fire pit, patio, shaded gathering spots, and reading nooks in nature, and next to 366 acres of beautiful woods and picnic areas along an 84 acre lake that will soon be fully renovated. This home sleeps 20+ people with five private sleeping rooms and has had all kinds of multi family stays and a great variety of retreats, weddings, and other notable celebrations. 

One of the best places to stay in Iowa! Epic events take place inside and outside this home. Schedule your gathering today! Plan a wedding anniversary with live music in the back yard, a beauty spa in the dining room while a baby-sitter plays with the children in the pool, a chef cooking for and with your group, live music, family and friend reunions,  indoor and outdoor games and end the night with good times around the fire. This home sleeps 16-19 and has lots of large areas for entertaining. 

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. Fully stocked, open-concept kitchen with premium stainless steel appliances and a large island. 

Hidden butler’s pantry with a coffee bar, snack station, and plenty of extra prep space. This home sleeps 9 

Still Waters Iowa is a farm family cabin that can be used for events such as reunions, conferences, and holiday get togethers, as well as overnight stays. It is located just off of an active farmyard and is adjacent to a four acre pond. There is a recreation room with a basketball court, extra tables and chairs for a very large gathering and a full kitchen to prepare for the whole crew! Catering is available for your group. This space has held wedding receptions, large work parties, family reunions, and much more! The owners are full of adventure, love and kindness.

Cute, rustic cabin on the river. Relax with the whole family and friends, or have a quiet get away with someone special. Watch the sunset, relax in the screened porch, have a fire and tell stories by one of the fire pits, fish the DesMoines river or cozy up to the indoor fireplace in the winter. There is a fully stocked kitchen, no oven at the moment but hot plate burners available, air fryer, and electric grill. This cabin sleeps 10 guests, and is sure to be a space where reconnection and inspiration can take place. 

Make yourselves at home in our Sunny Cottage. Many return guests say it's their favorite home in Oskaloosa.  It's been a writer's retreat, girls getaway, hunting stay, race fans home away from home, brides and bridesmaids, bride and groom, a whole lot of college students' parents, and more! Come make it your garden for as long as you'd like! 

Experience luxury and comfort amidst curated vintage treasures and a library collection for all ages and interests. The outdoors complements this home's appeal with an outdoor patio and a peaceful back yard with beautiful shady reading and conversation areas. Occasionally we have short term stays here, but it is usually taken by traveling professionals. 

Up in the trees and two blocks from downtown, this 2 bedroom, 1 1/2 bath upscale condo with attached garage is your home for a month or more. Laundry in suite. Master bedroom has a king bed and in suite half bath. Guest bedroom has a full bed with extra blankets and pillows in the closet as needed. 

Kick back and relax in this vibrant, peaceful space. This stylish open living space is conveniently located a few blocks from the town center on a large yard and the three bedrooms have been occupied by professionals in the area for work or by families visiting people in Oskaloosa. 

This two bedroom one bath home with a large deck out back can be rented alone or with the two bedroom Garden Loft above, if available. Occasionally it is available for short term rentals; it is usually occupied by a professional or family needing a home for several months. 

The day after photos were taken, we welcomed our second guest who wanted a place to stay in Oskaloosa for a few months. This loft, just a few blocks from Oskaloosa's historic downtown gives your a private space to get away, yet close to everything Oskaloosa.

Come stay at this fun second floor condo in the heart of Oskaloosa, recently featured by Olio in Iowa.  Walk out your door to a bakery, across the street to wings, pizza or a salad and one block to an award winning square with an idyllic coffee shop, boutiques, thrift stores, art center, history walk and more. 

Come stay at this fun second floor condo in the heart of Oskaloosa, recently featured by Olio in Iowa.  Walk out your door to a bakery, across the street to wings, pizza or a salad and one block to an award winning square with an idyllic coffee shop, boutiques, thrift stores, art center, history walk and more.