Holiday rentals 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!

Historic Home on 4 Acres - Hot Tub, Pool, Tiki Bar

Our 1948 vacation home is on 4 acres & boasts 3 bedrooms, 3 full baths, 2 half baths, Bridal Suite (4th bedroom), 70s TV/Game Room, Tiki Bar, & Children's Playroom. Outside we have a pool (guaranteed to be open 5/26 - 9/5) & hot tub (year round). Located 15min away from Downtown DSM & a mile away from a grocery store/restaurants. Up to 2 dogs allowed for an additional fee. ***Events/photo shoots are allowed with written permission only and will be an added fee. No events larger than 25 total.***

RARE Spacious Treehouse & Sauna Near Des Moines

Come home to luxury in nature in this spacious, double king-bed treehouse and sleep among the stars. Expansive views of rolling hills greet you as you sip your pour-over coffee on the wrap around balcony twenty feet above ground. Rain? No problem. Tuck away on the three-season screened-in porch to watch the iconic Iowa pink sunsets. Built with special touches including stained glass and intricate woodwork, this treehouse boasts warmth throughout and is sure to be a once-in-a-lifetime get-away.

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.

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.

The Norwood

Your family will be close to everything when you stay at this centrally-located place. very close to the Iowa state Fair, Adventureland Park,Grandview Golf Course,Shops of Iowa,Teachout swimming Pool,Grandview Park Sargent's Park, Grace Church,Hilltop Restraunt (highly recommend) Restraunts . Grocery stores, gas stations, {Caseys, Quick Trip, Git N GO, Kum N Go, Kwik Star] Bike Trails, Shopping, Interstate 235 & I-80. right inbetween Des Moines, Altoona, close to Pleasant hill, Bondurant

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.

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

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.*

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.

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.

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.