Holiday houses in Pleasant Hill

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.***

Location · Family · Getting around

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.

Location · Family · Nearby

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 · Checkout

New A-Frame Cabin by Des Moines (Milkweed theme)!

Make some memories at this unique and family-friendly place. Escape to one of our three brand-new, fully furnished A-frame cabins at River Oaks RV Park—where modern comfort meets rustic charm. Each A-frame is uniquely designed, stylishly appointed, and perfect for making unforgettable memories. Whether you’re relaxing by the river, roasting s’mores under the stars, or just soaking in the cool, creative vibe of your private space, this family-friendly getaway is anything but ordinary.

Location · Family · 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

Family · Location · Kitchen

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.

Location · Family · Layout

8000sqft Barndo | Indoor Court + 2 Living Qtrs

Welcome to The Lodge on 3rd - a massive 8000 sq ft Barndominum. Nestled in the heart of Des Moines, Iowa, this stunning retreat offers the perfect blend of rustic charm and modern elegance. With 4 spacious bedrooms and a large loft, there is plenty of room for you and your guests to unwind in style. This property is next door to Luxury Living on Third. airbnb.com/h/luxurylivingonthird These combined properties are ideal for family reunions, etc. ***$200 Pet Fee***

Location · Family · Pool

Cozy Retreat | Steps to Yellow Banks Park Sleeps 6

Escape to this charming, fully renovated home nestled in a peaceful, scenic setting. Designed for comfort & relaxation, with access to nature right out your back door. Two queen bedrooms + 1 full bathroom upstairs, plus a bonus queen bed in unfinished basement. Surrounded by mature trees and open skies, enjoy a private, quiet atmosphere just steps from outdoor fun. Perfect for an adventure or a serene retreat close to nature. We look forward to hosting you!

Family · Location · Decor

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 · Walkability

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.

Location · Family · Bathroom

Wells Fargo - Huge King Bed Loft - Free Parking

Discover the heart of Des Moines in this vibrant downtown Airbnb! Nestled in the best locale, steps away from nightlife, historical landmarks, groceries, diverse dining, and lively bars. - King bed loft - 12.5 foot ceilings - Walk to Wells Fargo Arena - Walk to Science Center - Private balcony - Restaurants, bars, nightlife and coffee nearby - Fully stocked kitchen - Free parking included - 65" smart TV and Roku - Roll away bed

Location · Value · Pets

Restored Victorian, Walk & Bike

Completely restored Victorian home that is walking and biking distance to the East Village, Civic Center, Wells Fargo, world-renowned skate park, and the Iowa Capitol! Bring your bike and enjoys the trails (and indoor bike parking). Walk to a concert at Wells Fargo or a show at the Civic Center. We are dedicated to making your stay simple and easy. This house is special to us, and we want to share it with you!

Value · Family · Indoor spaces