Holiday houses in Pleasant Hill

Modern Luxury • Hot Tub • Game Room • Pickleball

Escape to this modern Midwest retreat in a peaceful neighborhood just 15 minutes from top Des Moines attractions. Clean, spacious, and designed for comfort and convenience, the home features two en-suite masters, a spa-style soaking tub and rainfall shower, a game room, and a fully equipped open-concept kitchen. Enjoy a private outdoor oasis with a hot tub and fire pit in a fenced yard. Pickleball courts and a playground are just steps away. This home is perfect for relaxing and making memories!

Value · Location · Hot tub

Family Friendly Spacious House W/ Gameroom

Nestled in a quiet residential neighborhood, this home offers the perfect balance of peace and convenience—ideal for families, groups, or travelers visiting the Des Moines area. Inside, you’ll find a clean, cozy space designed for comfort and ease. Whether you’re here for a weekend getaway or an extended stay, the home is thoughtfully set up to help you relax after a long day. Enjoy spacious living areas, comfortable sleeping arrangements, and all the essentials you need for a stress-free stay.

Family · Location · Checkout

CozyHouse w/ HotTub, Sleeps 8,3BR,2BA,2LvngRms

Old world charm with modern conveniences! 2 Living Areas, 3 bedrooms, 2 baths, large patio with HOT TUB. plenty of seating and fire pit. Laundry, privacy-fenced yard. 72" TV in main level living room, 55" upstairs; all bedrooms have TV's with Roku. Quiet residential neighborhood. 5 minutes to Adventureland, Prairie Meadows Racetrack/Casino and the Outlets of Des Moines. 10 minutes to the Iowa State Fairgrounds and 15 minutes to downtown Des Moines. Garage space not included. Bedding may vary.

Location · Family · Decor

Walk to Fairgrounds! | Cozy Bungalow | Fenced Yard

Welcome to the Fairgrounds Bungalow: Your Cozy Escape with Vintage Charm! Step into a one-of-a-kind getaway at our charming Fairgrounds Bungalow, where modern comfort meets nostalgic vibes. This inviting home is perfect for families, small groups, or couples seeking a unique stay near the heart of the Iowa State Fairgrounds. Property includes a cozy 2 bedroom bungalow, vintage camper and a game shed. Very dog friendly! Please include in your reservation dog guests as well(up to two).

Value · Family · Quiet

Fairground Boho Bungalow

Have fun with family or friends at this stylish bungalow. One block from the west gates of the historic fairgrounds. Less than 3 miles from the East Village in beautiful downtown Des Moines. This property allows for pets offering a fenced in backyard. Amenities include a full kitchen, dishwasher, electric range, refrigerator, propane barbecue grill, and outdoor seating. There is offstreet parking that will accommodate two vehicles as well as free parking along the street.

Family · Location · Cleanliness

The Office - Pet Friendly Duplex near Downtown!

“The Office" is a 2-bedroom, 1-bathroom Dunder Mifflin themed duplex near downtown Des Moines. It's decorated with inspiration from the TV show. The duplex has a kitchen (but no stove), a comfy TV watching area, and offers a unique and central location with a large driveway. Whether you’re a die-hard fan or have never watched an episode, the Office is designed to be a comfortable and welcoming place for everyone. Traveling with a group? Check out our adjoining Airbnb, the Rosebud!

Family · Location · Condition

A Touch of Pleasant

Welcome travelers! Enjoy a quiet and comfortable stay in our ranch-style home with a private entrance to the lower-level apartment. You'll have a spacious living room, bedroom, bathroom, home theater, and cozy kitchen with a dining area. Whether you're in town for business or leisure, our clean, quiet space provides a restful retreat. We look forward to hosting you! Easy access to bike trails 10 mins to fairgrounds 15 mins to Downtown 15 mins Altoona Outlets 20 mins Airport

Location · Family · TV

Walk to the fair! Santorini Retreat: sleeps 5

Escape to your own slice of Santorini in the heart of Des Moines! This Mediterranean-inspired retreat features a private hot tub, fully fenced yard, dog run, kids’ play area, outdoor games, and a signature indoor swing bed perfect for relaxing. Enjoy the patio lounge and outdoor dining area with premium outdoor speakers for the perfect staycation vibe. Walking distance to the Iowa State Fairgrounds! *NOTE: Main house ONLY; detached backyard guest cottage (ADU) not included.*

Family · Value · Decor

Windy Pines Suite

Windy Pines offers a spacious bedroom with a comfortable king sized bed and large bathroom. The kitchen and living room are great. This clean, comfortable, & uncluttered space is a home away from home! You will be surrounded by beautiful greenery, in a safe neighborhood with accessible parking. Close to interstate 80 & 35, the Iowa State Fair Grounds, and Downtown Des Moines. WP is attached to our home but with its own separate outside entrance. Please send me any questions.

Family · Location · Check-in

Cozy bungalow steps away from IA State Fairgrounds

Located just steps away from the Iowa State Fairgrounds, this cozy bungalow will make you feel right at home. Whether you're here for one of the many events at the Fairgrounds or just visiting Des Moines, this house has just what you need to make your stay comfortable and convenient. The house is located on a 4-lane, main city street so please be aware if you are sensitive to noise. However, majority of guests don't notice any noise disturbances.

Value · Family · Comfort

Large Home Near Adventureland, Fair, downtown DSM

Speedy access to the best that Des Moines and eastern Polk County have to offer--downtown, the fairgrounds, and Adventureland! Spacious, comfortable, and classic home tucked away in a quiet, lush, established Pleasant Hill neighborhood just minutes away from most of the capital's popular destinations. The Hill on Tyler provides space for multi-family getaways or medium- and large-sized groups. Walking and biking trails are quite close.

Family · Location · Decor

Cozy 2 bed place with outdoor oasis.

Take it easy at this unique and tranquil getaway. We are less than 3 miles from the Iowa state fairgrounds, 6 miles from downtown Des Moines, and 8 miles from Des Moines International Airport. Please note that from October-April we are willing to negotiate longer term stays (multiple consecutive weeks or months) for a much lower rate, pending availability. Please send an inquiry if interested.

Family · Value · Check-in