Holiday houses in Pleasant Hill

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Top-rated holiday rentals in Pleasant Hill

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Home in Pleasant Hill
5 out of 5 average rating, 28 reviews

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!

Top Guest favourite
A treehouse, elevated on stilts, is surrounded by various trees and greenery. The wooden structure features large windows and a balcony, with a staircase leading up, inviting guests to its elevated entrance. Bright blue skies provide a clear backdrop.
Treehouse in Norwalk
5 out of 5 average rating, 99 reviews

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.

Top Guest favourite
Home in Altoona
4.97 out of 5 average rating, 93 reviews

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.

Superhost
Home in Des Moines
5 out of 5 average rating, 4 reviews

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.

Top Guest favourite
An outdoor patio area features a decorative brick fireplace with an oven. Two cushioned chairs are arranged around the fireplace, providing a comfortable space to relax. A patterned rug lies beneath, enhancing the setting. Colorful potted flowers are visible in the background.
Guest suite in Pleasant Hill
4.97 out of 5 average rating, 39 reviews

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

Top Guest favourite
An open living area showcases comfortable seating and a decorative ottoman on a dark rug. The kitchen is visible in the background, featuring wooden cabinetry and appliances. Walls are adorned with framed art, contributing to a well-appointed and welcoming space.
Guest suite in Pleasant Hill
5 out of 5 average rating, 239 reviews

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.

Top Guest favourite
A spacious living area features a modern design with a large sofa and two green accent chairs. A sleek entertainment unit with a fireplace is centered on the wall. Large windows provide natural light, enhancing the open and airy atmosphere.
Barn in Des Moines
5 out of 5 average rating, 172 reviews

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***

Top Guest favourite
A queen-size bed is centered against a light grey wall, dressed in crisp white linens. Accent pillows in soft teal are positioned at the head of the bed. A decorative sign rests above the bed, and a nightstand with a lamp is visible to the side.
Home in Bondurant
4.98 out of 5 average rating, 204 reviews

Quintessential Iowa Stay -Quiet, Cozy & Convenient

Bring the family and settle into our newer ranch home in tranquil Bondurant — just minutes from Des Moines and all the area’s top attractions! *Adventureland Park 2 miles *Prairie Meadows Casino 2 miles *Outlets of DSM 2 miles *Civic Center 12 miles *Jack Trice Stadium Ames 34 miles *Newton Speedway 27 miles *The District at Prairie Trail Ankeny 12 miles *Blank Park Zoo 17 miles *Iowa State Fairgrounds 11 miles *Des Moines Farmers’ Market 12 miles

Superhost
A welcoming living area features a light gray couch and a beige armchair with a soft throw pillow. A small blue ottoman sits nearby. Natural light enters through two large windows, complemented by a green plant and a decorative mirror on the wall. A small table holds a flower arrangement.
Bungalow in Des Moines
4.83 out of 5 average rating, 255 reviews

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.

Top Guest favourite
A spacious living area features a gray sectional sofa adorned with a mix of pillows in earthy tones. A glass-top coffee table sits at the center, holding stacked books and a decorative bowl. Natural light filters through the large windows, creating a warm ambiance.
Home in Pleasant Hill
4.85 out of 5 average rating, 177 reviews

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.

Top Guest favourite
Tiny home in Des Moines
4.94 out of 5 average rating, 113 reviews

Rittenhouse Inn

Enjoy the convenience of being less than a 5 minute drive from the Des Moines International Airport and 10 minutes from Downtown DSM. Tucked away in a residential neighborhood, Rittenhouse Inn, is an eclectic tiny house that is well equipped for the modern day traveler. Set back from the road, the Inn can serve as a secluded place to relax and unwind, or a convenient basecamp for whatever adventure awaits you.

Top Guest favourite
A serene outdoor area is depicted, featuring two white plastic chairs placed on a wooden platform nestled among lush green plants. A small stream flows gently beside the platform, while tall green grass and leaves frame the peaceful setting.
Guest suite in Pleasant Hill
4.92 out of 5 average rating, 291 reviews

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.

Popular amenities for Pleasant Hill holiday rentals